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

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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

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1986, Belgium

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	Hungary/Denmark
Date inclusion expires	31/12/2021
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes

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

Chemical structure:

Isomerism	A chiral molecule. Technical tefluthrin is a 1:1 mixture of Z-(1R, 3R) and Z-(1S, 3S) enantiomers.
Chemical formula	C17H14ClF7O2
Canonical SMILES	CC1=C(C(=C(C(=C1F)F)COC(=O)C2C(C2(C)C)C=C(C(F)(F)F)Cl)F)F
Isomeric SMILES	CC1=C(C(=C(C(=C1F)F)COC(=O)[C@H]2[C@H](C2(C)C)/C=C(/C(F)(F)F)\Cl)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

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
PubChem CID	11534837
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	-
Relevant Environmental Water Quality Standards	-
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	silica fludioxonil toluene 2,4-diisocyanate

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 20oC (mPa)		8.4	A5	Moderately volatile
Henry's law constant at 25oC (Pa m3 mol-1)		2.00 X 1002	A5	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
General biodegradability		-
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	-
	DT50 modelling endpoint	-	-	-
	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
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	11.2	A4	Moderately fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	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	1107/2009 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	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
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 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		Highly toxic Possible thyroid and CNS 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		Health: H300, H310, H330, H372 Environment: H400, H410
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	-

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Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk