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

Destino ambiental - Ecotoxicología - La salud humana - A a Z Indice - Inicio

RESUMEN

Bifenthrin is a pyrethroid insecticide used to control a range of pests. It has a low aqueous solubility and is volatile. There is a low risk of groundwater contamination based on its chemical properties and it is not persistent in soil. There are some concerns about bioaccumulation and the pesticide shows a high oral toxicity to mammals as well as being an endocrine distupter and a neurotoxicant. It is toxic to birds, most aquatic organisms, honeybees and earthworms.

INFORMACIÓN GENERAL Click here for an explantaion of the general chemical status information
for bifenthrin

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

Ejemplos de plagas controladas: Fire ants; Blue grass weevil; Armyworms; Cutworms; centipedes; Crickets; earwigs; Millipedes; Sowbugs; Mole crickets; Ticks; Fleas; Grasshoppers

Ejemplos de aplicaciones: Non-cropped situations including lawns, athletic fields, ornamentals, residences and commercial buildings

Eficacia y actividad: -

Availability status: Current

Introduction & key dates: circa 1984

CEE Regulación 1107/2009 ( 91/414):
Estado Approved
Dossier rapporteur/co-rapporteur Belgium/Hungary
Date inclusion expires 31/07/2021
UE Candidatas a sustitución Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
Incluido en la base de datos de la UE

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

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, Estados Unidos

Estructura química: Click here for further information on the general chemical status information used on this site
Isomerism Bifenthrin is chiral molecule and is a mixture of the Z-isomer (~99.7%) and the E-isomer (~0.3%).
Fórmula química C23H22ClF3O2
Canonical SMILES CC1=C(C=CC=C1COC(=O)C2C(C2(C)C)C=C(C(F)(F)F)Cl)C3=CC=CC=C3
Isomeric SMILES CC1=C(C=CC=C1COC(=O)[C@@H]2[C@@H](C2(C)C)/C=C(/C(F)(F)F)\Cl)C3=CC=CC=C3
International Chemical Identifier Key (InChIKey) OXCDWLBJSLVWHB-LKRLXIKPSA-N
International Chemical Identifier (InChI) InChI=1S/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-
¿Diagrama de estructura 2D / imagen disponible?

Estado general: Click here for further information on the general chemical status information used on this site
Tipo de pesticida Insecticide, Acaricide
Grupo químico Pyrethroid
Minimum active substance purity 930 g/kg
Known relevant impurities EU dossier - Toluene <5 g/kg
Sustancias de origen Sintéticas
Modo de acción Contact and stomach action with some residual effect. Sodium channel modulator.
CAS RN 82657-04-3
CEE número -
Número CIPAC 415
EPA américaine chimiques de code 128825
PubChem CID 6442842
Masa molecular (g mol-1) 422.88
PIN (Preferred Identification Name) rac-(2-methyl[1,1'-biphenyl]-3-yl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
Nombre IUPAC 2-methyl-3-phenylbenzyl (1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Nombre CAS (2-methyl(1,1'-biphenyl)-3-yl)methyl (1R,3R)-rel-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
Otra información de estado -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) No aplicable
Herbicide Resistance Classification (WSSA) No aplicable
Insecticide Resistance Classification (IRAC) 3
Fungicide Resistance Classification (FRAC) No aplicable
Examples of recorded resistance Bemisia argentifolii
Frankliniella occidentalis
Plutella xylostella
Tetranychus turkestani
plus others
Estado físico Off-white waxy solid
Related substances & organisms

Formulaciones:
Propiedad Click here for information on the general product and branding information used on this site Valor
Example manufacturers & suppliers of products using this active now or historically
  • 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
Estado de UK LERAP Buffer probably required in UK - see product label
Formulation and application details Often supplied as a soluble or emulsifiable concentrate which is mixed with water and applied as a spray.


DESTINO AMBIENTAL

for bifenthrin

Propiedad Click here for information on the parameters used to describe environmental fate on this site Valor Fuente/Cuenta de Cualidad/Otra Información Click here for information on the primary data sources used to populate this database with fate data Interpretación Click here for information on the way in which we interpret environmental fate data
Solubilidad - En aqua en 20oC (mg l-1) 0.001 A5 Bajo
Solubilidad - en solventes organicos en 20oC (mg l-1) 735700 A5 - Acetona -
144500 A5 - n-Heptano -
48000 A5 - Metanol -
556300 A5 - Xileno -
Punto de fusión (oC) 79.6 A5 -
Punto de ebullición (oC) Decomposes before boiling A5 -
El punto de degradación (oC) 280 A5 -
Punto de inflamación (oC) 151 L3 - (closed cup) -
Octanol-aqua coeficiente de particiónat en pH 7, 20oC P 3.98 X 1006 Calculado -
Log P 6.6 A5 Alto
Masa densidad (g ml-1)/Peso específico 1.26 A5 -
Disociación constante (pKa) at 25oC No aplicable H3 -
Nota: Ninguna disociación
Presión de vapor en 20oC (mPa) 0.0178 A5 Baja volatilidad
Constante de Henry a 25oC (Pa m3 mol-1) 7.74 X 10-05 A5 No volátil
Indice de potencial de lixiviación GUS Click here for a note on the limitations of the GUS index -2.76 Calculado Bajo posibilidad de lixiviación
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Valor 5.35 X 10-03 Calculado -
Nota 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
Potencial para transportar de 'particle bound' Click here for a note on the limitations of the potential for particle bound transport index - Calculado Mediano
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) - - -

Degradación:
Propiedad Click here for information on the parameters used to describe substance degradation Valor Fuente/Cuenta de Cualidad/Otra Información Click here for information on the primary data sources used to populate this database with degradation data Interpretación Click here for information on the way in which we interpret substance degradation data
Biodegradabilidad general -
Degradación de suelo (días) (aerobic) DT50 (típico) 26 Q3 No persistente
DT50 (laboratorio en 20oC) 102.2 A5 Persistente
DT50 (campo) 86.8 A5 Persistente moderado
DT90 (laboratorio en 20oC) 346.5 A5 -
DT90 (campo) 3410.8 A5 -
Endpoint de modelado DT50 - - -
Nota 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.
Dissipation rate RL50 on plant matrix Valor 6.1 R4 -
Nota Published literature RL50 range 1.3-27.0 days, 5 field & undercover grown crops, various matrices, n=6
Dissipation rate RL50 on and in plant matrix Valor 4.5 R4 -
Nota Published literature RL50 range 0.8-14.0 days, 11 field & undercover grown crops, various matrices, n=20
Acuoso fotólisis DT50 (días) en pH 7 Valor 12 B5 Moderado rápido
Nota DT50: 255 days in natural sunlight, 12 days in artifical light
Acuoso hidrólisis DT50 (días) en 20oC y pH 7 Valor Estable A5 -
Nota Stable pH 5 to pH 9 at 25 degC. Hydrolysis occurs at elevated temperatures e.g. DT50 20 mins at pH 4, 90 degC
Aqua-Sedimento DT50 (días) 161 A5 Lento
Fase de agua sola DT50 (días) 8 K4 Moderado rápido

De absorción del suelo y la movilidad:
Propiedad Click here for information on the parameters used to describe substance adsorption and mobility Valor Fuente/Cuenta de Cualidad/Otra Información Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretación Click here for information on the way in which we interpret substance adsorption and mobility
Lineal Kd 3567 A5 No Móvil
Koc 236610
Notas y rango EU dossier Kd range 992-5429 mL/g, Koc range 130526-301611 mL/g, Soils=4
Freundlich Kf - - -
Kfoc -
1/n -
Notas y rango -
pH senbsibilidad No

Key metabolites:
Metabolito Medio de formación Maximó Calculado de Fracción Ocurrencia 1107/2009 Importancia Click here for further information on 1107/2009 relevancy
(1RS,3RS)-3-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid This metabolite may cause environmental pollution, click here for further information Suelo   0.116   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Medio de formación / Rate Maximó Calculado de Fracción Ocurrencia 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 - -


ECOTOXICOLOGÍA

for bifenthrin

Propiedad Click here for information on the parameters used to describe substance ecotoxicology Valor Fuente/Cuenta de Cualidad/Otra Información Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretación Click here for information on the way in which we interpret substance ecotoxicology
Factor de la bio-concentración BCF (l kg-1) 1703 E4 Umbral de importancia
CT50 (días) No disponible -
Mamíferos - Agudos oral LD50 (mg kg-1) 54.5 A5 Rata Alto
Mamíferos - a corto plazo NOEL (mg kg-1) > 5 B5 Rata Alto
(ppm dieta) > 100 -
Pájaros/aves - Agudos LD50 (mg kg-1) 1800 A5 Colinus virginianus Moderado
Birds - Short term dietary (LC50/LD50) 4450 mg kg feed-1 A5 Colinus virginianus -
Pez - agudo 96 hora LC50 (mg l-1) 0.00026 A5 Oncorhynchus mykiss Alto
Pez - Crónico 21 días NOEC (mg l-1) 0.000012 A5 Salmo gardneri Alto
Invertebrados acuáticos - Agudos 48 hora EC50 (mg l-1) 0.00011 A5 Daphnia magna Alto
Invertebrados acuáticos - Crónicos 21 días NOEC (mg l-1) 0.0000013 A5 Daphnia magna, LOEC Alto
Crustáceos acuáticos - Agudos 96 hora LC50 (mg l-1) 0.0000012 A5 Americamysis bahia Alto
Sediment dwelling organisms - Agudos 96 hora LC50 (mg l-1) - - -
Sediment dwelling organisms - Crónicos 28 día NOEC, estático, agua (mg l-1) 0.00032 A5 Chironomus riparius Alto
Sediment dwelling organisms - Crónicos 28 día NOEC, sedimento (mg kg-1) - - -
Plantas acuáticas - Agudos 7 día EC50, biomasa (mg l-1) - - -
Non-target plants - - -
- - -
Algas - Agudos 72 hora EC50, crecimiento (mg l-1) 0.822 A5 Scenedemus subspicatus Moderado
Algas - Crónicos 96 hora NOEC, crecimiento (mg l-1) 10 Q2 Unknown species Bajo
Abejas mielíferas Contacto aguda 48 hora LD50 (μg abeja-1) 0.016 A4 Apis mellifera Alto
Oral aguda 48 hora LD50 (μg abeja-1) 0.1 A5 Apis mellifera Alto
Modo desconocido aguda 48 hora LD50 (μg abeja-1) - - -
Lombrices - Agudos 14 día LC50 (mg kg-1) > 8.0 A5 Eisenia foetida, corr Alto
Lombrices - Crónicos 14 día NOEC, reproducción (mg kg-1) 1.065 A5 Eisenia foetida, 56 días corr Moderado
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Causalidad - - -
Otro arthropoda (1) LR50 g ha-1 - - -
% Causalidad 100 Mortalidad
Dose: 60g ha-1
A5 Aphidius rhopalosiphi
-
Otro arthropoda (2) LR50 g ha-1 0.113 A5 Typhlodromus pyri -
% Causalidad 100 Mortalidad
Dose: 60g ha-1
A5 Typhlodromus pyri
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.128 mg kg-1
-
Mesocosm study data NOEAEC mg l-1 0.000015 A5 Gammarids, copepods & chaoboridae -
NOEAEC mg l-1 - - -


LA SALUD HUMANA Y PROTECCIÓN

for bifenthrin

General:
Propiedad Click here for information on the parameters used to describe human health and protection issues Valor Fuente/Cuenta de Cualidad/Otra Información Click here for information on the primary data sources used to populate this database with human health and protection data Interpretación Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mamíferos - Agudos oral LD50 (mg kg-1) 54.5 A5 Rata Alto
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 1.01 A5 Rat, 4 hr -
Other Mammal toxicity endpoints - -
Consumo cada día aceptable (mg kg-1p.c. días-1) 0.015 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1p.c. días-1) 0.03 A5 Rat, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
El nivel de exposición del operador (AOEL) sistemíco (mg kg-1p.c. días-1) 0.0075 A5 Dog, SF=100 -
Estudios den la absorción cutánea (%) 18 A5 -
Directivo 76/464 Sustancias Peligrosas Lista II - -
Limites de exposiciones - - -
Exposure Routes Public Bystanders should not access orchards or vineyards during spraying
Occupational Some risk identified especially during orchard spraying - PPE advised
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) 0.1 EU Dir 89/778/EC limit; Calc MAC=45.0 μg l-1; A5 -

Health issues:
Carcinogen Mutágeno Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

Cuestiones generales de la salud humana May cause tremors and staggered gait
USEPA - possible human carcinogen

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

Handling issues:
Propiedad Click here for information on the parameters used to describe substance handling issues Valor Fuente/Cuenta de Cualidad/Otra Información Click here for information on the primary data sources used to populate this database with data on handling issues Interpretación Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H300, H317, H331, H351, H372
Environment: H400, H410
CEE clasificación de riesgos Click here to view information omn the EU risk phrases Carcinogen category 3: R40
T - Toxic: R25, R23
Xn - Harmful: R22, R48
N - Dangerous for the environment: R50, R53
CEE clasificación sin riesgos Click here to view information omn the EU safety phrases -
Clasificación de OSM II - Peligroso mediano
US EPA Classification (formulation) II - Warning - Moderately toxic
Número de las NU 3349
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRADUCCIONES

for bifenthrin

Idioma Nombre
Inglés bifenthrin
Francés bifenthrine
Alemán Bifenthrin
Danés bifenthrin
Italiano bifentrin
Español bifentrin
Griego -
Esloveno bifentrin
Polaco bifentryna
Sueco -
Húngaro bifenthrin
Holandés -

Última actualización del registro: Friday 24 May 2019
Contacto: aeru@herts.ac.uk