bifenthrin (Ref: FMC 54800) ** bifenthrine ** biphenthrin ** biphentrin ** biphenate ** Translations

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GENERAL INFORMATION

Description: A pyrethroid acaricide/insecticide for use in a wide range of crops to control sucking and biting foliar pests

Introduction: circa 1984

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

Status	Pending (Re-submitted)
Dossier rapporteur/co-rapporteur	France
Date inclusion expires	-

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	Insecticide, Acaricide
Substance group	Pyrethroid
Substance origin	Synthetic
Mode of action	Contact and stomach action with some residual effect. Sodium channel modulator.
CAS RN	82657-04-3
EC number	-
CIPAC number	415
US EPA chemical code	128825
Chemical formula	C23H22ClF3O2
SMILES	Cl\C(=C/C3C(C(=O)OCc2cccc(c1ccccc1)c2C)C3(C)C)C(F)(F)F
International Chemical Identifier (InChI)	InChI=1/C23H22ClF3O2/c1-14-16(10-7-11-17(14)15-8-5-4-6-9-15)13-29-21(28)20-18(22(20,2)3)12-19(24)23(25,26)27/h4-12,18,20H,13H2,1-3H3/b19-12-
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	422.88
IUPAC Name	2-methyl-3-phenylbenzyl (1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
CAS Name	(2-methyl[1,1'-biphenyl]-3-yl)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
Insecticide Resistance Classification (IRAC)	3
Fungicide Resistance Classification (FRAC)	Not applicable
Physical state	Off-white waxy solid
Related substances & organisms	malathion

Formulations:

Property	Value
Example manufacturers of products using this active	Belchim Certis FMC Chemicals Lapafarm INC United Phosphorus
Example products using this active	Gala 10 EC Gyro Starion Flo Talstar Flo Brigade Talstar 8 SC
UK LERAP status	LERAP Category A, Broadcast Air Assisted LERAP
Formulation and application details	Often supplied as a soluble or emulsifiable concentrate which is mixed with water and applied as a spray.

ENVIRONMENTAL FATE

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		0.001	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		735700	A5 - Acetone	-
		144500	A5 - n-Heptane	-
		48000	A5 - Methanol	-
		556300	A5 - Xylene	-
Melting Point (oC)		79.6	A5	-
Boiling Point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		280	A5	-
Flashpoint (oC)		151	L3 - (closed cup)	-
Octanol-water partition coefficient at pH 7, 20oC	P	3.98 X 1006	Calculated	-
	Log P	6.6	A5	High
Bulk density (g ml-1)/Specific gravity		1.26	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	H3	-
		Note: No dissociation
Vapour pressure at 25oC (mPa)		0.0178	A5	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		7.74 X 10-05	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		4.10 X 10-02	K3	Volatile
GUS leaching potential index		-1.94	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		All pH's: 250nm = 3282.9, sigificant absorption 290-300nm	A5	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	26	Q3	Non-persistent
	DT50 (lab at 20oC)	102.2	A5	Persistent
	DT50 (field)	86.8	A5	Moderately persistent
	DT90 (lab at 20oC)	346.5	A5	-
	DT90 (field)	3410.8	A5	-
	Note	EU dossier lab studies DT50 range 54.2-173.7 days, DT90 range 223-577 days, field studies DT50 range 5.4-267 days, DT90 range 135.3-965.2 days; Other studies DT50 (1) range 65-125 days, (2) range 2-6 months depending on soil type.
Aqueous photolysis DT50 (days) at pH 7	Value	12	B5	Moderately fast
	Note	DT50: 255 days in natural sunlight, 12 days in artifical light
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	Very persistent
	Note	Stable pH 5 to pH 9 at 25 degC. Hydrolysis occurs at elevated temperatures e.g. DT50 20 mins at pH 4, 90 degC
Water-Sediment DT50 (days)		161	A5	Slow
Water phase only DT50 (days)		8	K4	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	3567	A5	Non-mobile
	Koc	236610
	Notes and range	EU dossier Kd range 992-5429 mL/g, Koc range 130526-301611 mL/g, Soils=4
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		No

Key metabolites:

Metabolite		Formation Medium	Estimated Maximum Occurrence Fraction	91/414 Relevancy
(1RS,3RS)-3-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid		Soil	0.116	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation Medium / Rate	Estimated Maximum Occurrence Fraction	Metabolising Enzymes
(2-methylbiphenyl-3-yl)methyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2-(hydroxymethyl)-2-methylcyclopropanecarboxylate	OH-methyl bifenthrin	Animal; Hens (eggs); Soil	-	-
(4'-hydroxy-2-methylbiphenyl-3-yl)methyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylate	4'-OH bifenthrin	(a) Sediment; (b) Soil	b=0.08	-
2-methyl-3-phenylbenzoic acid	BP acid	Plant; Animal; Soil	-	-
2-methyl-3-phenylbenzyl alcohol	BP alcohol	Plant; Soil; Water	-	-

ECOTOXICOLOGY

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	1703	E4	Threshold for concern
	CT50 (days)	Not available		-
Bioaccumulation potential		-	Calculated	High
Mammals - Acute oral LD50 (mg kg-1)		54.5	A5 Rat	High
Mammals - Short term dietary NOEL	(mg kg-1)	> 5	B5 Rat	High
	(ppm diet)	> 100		-
Birds - Acute LD50 (mg kg-1)		1800	A5 Colinus virginianus	Moderate
Birds - Short term dietary (LC50/LD50)		4450 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		0.00026	A5 Oncorhynchus mykiss	High
Fish - Chronic 21 day NOEC (mg l-1)		0.000012	A5 Salmo gardneri	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.00011	A5 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.0000013	A5 Daphnia magna, LOEC	-
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.0000012	A5 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)		0.00032	A5 Chironomus riparius	High
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.822	A5 Scenedemus subspicatus	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		10	Q2 Unknown species	Low
Honeybees - Acute 48 hour LD50 (µg bee-1)		0.1	A5 Oral	High
Earthworms - Acute 14 day LC50 (mg kg-1)		> 8.0	A5 Eisenia foetida, corr	High
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		1.065	A5 Eisenia foetida, orr, 56 day	Moderate
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	100	Mortality Dose: 60g ha-1 A5 Aphidius rhopalosiphi	Harmful
Other arthropod (2)	LR50 g ha-1	0.113	A5 Typhlodromus pyri	-
	% Effect	100	Mortality Dose: 60g ha-1 A5 Typhlodromus pyri	Harmful
Soil micro-organisms		Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect	A5 Dose: 0.128 mg/kg	-
Mesocosm study data	NOEAEC mg l-1	0.000015	A5 Gammarids, copepods & chaoboridae	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Mammals - Acute oral LD50 (mg kg-1)		54.5	A5 Rat	High
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		1.01	A5 Rat, 4hr	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.015	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.03	A5 Rat, SF=100	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.0075	A5 Dog, SF=100	-
Dermal penetration studies (%)		18	A5	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	[Bystanders should not access orchards or vineyards during spraying]
	Occupational	[Some risk identified especially during orchard spraying - PPE advised]
Examples of European MRLs (mg kg-1)	Value	Lettuce: 2.0; Brussel sprouts and cabbage: 1.0; Currants, strawberries, beans (with pods), barley grains, oat grains and wheat grains: 0.5; Pomes, blackberries and raspberries: 0.3; Broccoli, cauliflowers, stone fruit and grapes: 0.2; Cucumbers, summer squash, peas (with pods) and citrus: 0.1; Other vegetables, other fruit and other cereal grains: 0.05
	Note	[Current May 2007.] For the EU pesticides database click here
Drinking Water MAC (µg l-1)		0.1	EU Dir 89/778/EC limit; Calc MAC=45.0 µg/l; A5	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
						-
General human health issues		[Skin sensitiser], [May cause tremors and staggered gait]

: 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]
EC Risk Classification		[T - Toxic: R25], [Xn - Harmful: R20], [Xi - Irritant: R43], [N - Dangerous for the environment: R50, R53]
EC Safety Classification		-
WHO Classification		II	-	Moderately hazardous
US EPA Classification (formulation)		II	-	Warning - Moderately toxic
UN Number		3349
Waste disposal & packaging		[Usually Packaging Group III (minor danger)]

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