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tefluthrin (Ref: R 151993)
** tefluthrine ** Translations

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

GENERAL INFORMATION
for tefluthrin

Description: An insecticide used to control a wide range of soil pests including Coleoptera, Lepidoptera and Diptera

Example pests controlled: Springtails; Symphylids; Millipedes; Pygmy beetle; Fire ants; rootworms; Wireworms; White grubs

Example applications: Sugarbeet; Fodder beet; Cotton; Field corn; Popcorn

Availability status: Current

Introduction & key dates: 1986, Belgium

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Germany
Date inclusion expires 31/12/2021

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

Also used in: Australia

General status:
Pesticide type Insecticide
Substance group Pyrethroid
Minimum active substance purity 920 g/kg
Known relevant impurities EU dossier - hexachlorobenzene
Substance origin Synthetic
Mode of action Contact and respiratory action with some repellant effects. Sodium channel modulator.
CAS RN 79538-32-2
EC number -
CIPAC number 451
US EPA chemical code 128912
Chiral molecule Chiral, a specific isomer or a derivative of a chiral molecule
Chemical formula C17H14ClF7O2
SMILES Cl\C(=C/C2C(C(=O)OCc1c(F)c(F)c(c(F)c1F)C)C2(C)C)C(F)(F)F
International Chemical Identifier key (InChIKey) ZFHGXWPMULPQSE-SZGBIDFHSA-N
International Chemical Identifier (InChI) InChI=1S/C17H14ClF7O2/c1-6-11(19)13(21)7(14(22)12(6)20)5-27-15(26)10-8(16(10,2)3)4-9(18)17(23,24)25/h4,8,10H,5H2,1-3H3/b9-4-
Structure diagram/image available? Yes
Molecular mass (g mol-1) 418.73
PIN (Preferred Identification Name) rac-(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
IUPAC name 2,3,5,6-tetrafluoro-4-methylbenzyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylate
CAS name (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-rel-3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylate
Other status information -
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) 3
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Helicoverpa armigera
Pseudoplusia includens
Physical state Colourless solid
Related substances & organisms

Formulations:
Property Value
Example manufacturers & suppliers of products using this active now or historically
  • Syngenta
Example products using this active
  • Force ST
UK LERAP status None (may vary with mixtures)
Formulation and application details Often supplied as suspensions for preparation as a seed treatment.


ENVIRONMENTAL FATE
for tefluthrin

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 0.016 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 500000 A5 - Acetone -
500000 A5 - Hexane -
262000 A5 - Methanol -
500000 A5 - Toluene -
Melting point (oC) 44.6 A5 -
Boiling point (oC) 156 A2 - (1 mmHg) -
Degradation point (oC) 295 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 2.51 X 1006 Calculated -
Log P 6.4 A5 High
Bulk density (g ml-1)/Specific gravity 1.48 A5 -
Dissociation constant (pKa) at 25oC 9 L2 -
Note: Hydrolysis prevents accurate determination
Vapour pressure at 25oC (mPa) 8.4 A5 Volatile
Henry's law constant at 25oC (Pa m3 mol-1) 2.00 X 1002 A5 Volatile
Henry's law constant at 20oC (dimensionless) 2.00 X 10-02 K3 Volatile
GUS leaching potential index -2.76 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Value 5.35 X 10-03 Calculated -
Note Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW
Potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 211.7nm = 25400, 268.3nm = 1190 A5 -
Surface tension (mN m-1) 69.0 A5 at 20oC, 94.9% -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 37 A5 Moderately persistent
DT50 (lab at 20oC) 37 A5 Moderately persistent
DT50 (field) 27.1 A5 Non-persistent
DT90 (lab at 20oC) 83 A5 -
DT90 (field) 237.8 A5 -
Note EU dossier lab studies DT50 range 7-151 days, DT90 range 43-160 days; field studies DT50 range 9-206 days, DT90 range 31-686 days
Plant matrix DT50 (days) Value - - -
Note -
Aqueous photolysis DT50 (days) at pH 7 Value 11.2 A4 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 Very persistent
Note pH sensitive: stable pH 5 and pH 7, DT50 30 days at pH 9, all at 20 degC
Water-sediment DT50 (days) 72 K4 Moderately fast
Water phase only DT50 (days) 7 K4 Moderately fast

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd 1088 A5 Non-mobile
Koc 112900
Notes and range EU dossier Kd range 492-267000 mL/g, Soils=8
Freundlich Kf 3428 A5 Non-mobile
Kfoc 574088
1/n 1.1
Notes and range EU dossier range kf 332-14400; Kfoc range 46000-3600000 mL/g, 1/n 0.83-1.23; Soils=8
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
(1R,3R;1S,3S)-3-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid (Ref: PP890) Soil   0.071   Minor fraction, Not relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-1-methylcyclopropane-1,2-dicarboxylic acid tefluthrin Compound XII Plant - -
2,3,5,6-tetrafluoro-4-methylbenzoic acid tefluthrin Compound X; tefluthrin Compound III Soil (Anaerobic) - -
2,3,5,6-tetrafluoroterephthalic acid tefluthrin Compound IV Water 0.07 -
2,3,5,6-tetrafluoro-4-hydroxymethyl benzoic acid
(Ref: R173204) 		tefluthrin Compound V1 Animal - -
3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2-hydroxymethylcyclopropanecarboxylic acid
(Ref: R173948) 		tefluthrin Compound X1 Rat; Plant - -
2,3,5,6-tetrafluoro-4-methylbenzyl (Z) (1R,2R,3R; 1S,2S,3S)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2-hydroxymethyl-2-methylcyclopropanecarboxylic acid
(Ref: R177540) 		tefluthrin Compound IX Rat - -


ECOTOXICOLOGY
for tefluthrin

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF (l kg-1) 1400 A5 Threshold for concern
CT50 (days) 14 -
Mammals - Acute oral LD50 (mg kg-1) 21.8 A5 Rat High
Mammals - Short term dietary NOEL (mg kg-1) > 75 B5 Rat High
(ppm diet) > 150 -
Birds - Acute LD50 (mg kg-1) > 267 A5 Passer domesticus Moderate
Birds - Short term dietary (LC50/LD50) > 179 mg kg bw-1 day-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 0.00006 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) - - -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.00007 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.000008 A5 Daphnia magna High
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.00005 F3 Americamysis bahia High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) > 0.0025 A4 Chironomus riparius, 48 hour EC50 High
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) > 0.47 A4 Chironomus riparius, Reproduction Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) - - -
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 1.05 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.18 Q2 Unknown species Moderate
Honeybees Contact acute 48 hour LD50 (μg bee-1) 0.28 A5 High
Oral acute 48 hour LD50 (μg bee-1) 1.88 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 1.0 A5 Eisenia foetida, corr High
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 Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect 		A5
Dose: 0.75 kg ha-1, 28 days 		-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION
for tefluthrin

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) 21.8 A5 Rat High
Mammals - Dermal LD50 (mg kg-1 body weight) 177 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 0.037 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.005 A2 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.005 A2 Dog, SF=100 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.0015 A2 Dog, SF=100 -
Dermal penetration studies (%) 0.12 A5 -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public No unacceptable risks to bystanders identified
Occupational No unacceptable risks to operators or other workers identified with PPE/PPC
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 Highly toxic
Possible thyroid toxicant

: 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 None allocated at this time
EC Risk Classification T+ - Very toxic: R26/28
T - Toxic: R24
N - Dangerous for the environment: R50
EC Safety Classification -
WHO Classification Ib - Highly hazardous
US EPA Classification (formulation) I - Danger - Highly toxic
UN Number 3349
Waste disposal & packaging Packaging Group III (minor danger)


TRANSLATIONS
for tefluthrin

Language Name
English tefluthrin
French tefluthrine
German Tefluthrin
Danish tefluthrin
Italian teflutrin
Spanish teflutrin
Greek -
Slovenian teflutrin
Polish teflutryna
Swedish teflutrin
Hungarian teflutrin
Dutch -

Record last updated: Saturday 12 December 2015
Contact: aeru@herts.ac.uk