fipronil (Ref: BAS 350l) ** fipronil ** RPA 030 ** Traducciones

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Destino ambiental - Ecotoxicología - La salud humana - A a Z Indice - Inicio
Otros datos se pueden encontrar en el VSDB

RESUMEN

A broad-spectrun insecticide that is no longer approved for use in the EU on crops but may be used as a veterinary treatment, for the control of parasites on animals not destined for the food chain. It has a low aqueous solubility, a low volatility and is not greatly mobile in the environment. It can be quite persistent in soil systems but is less so in aquatic and sediment systems. It is highly toxic to humans and may bio-accumulate. It is considered a neurotoxicant and both an eye and skin irritant. Fipronil is highly toxic to mammals, birds and bees but slightly less so to fish, aquatic invertebrates, aquatic plants and earthworms.

INFORMACIÓN GENERAL
for fipronil

Descripción: An insecticide used to control a broad range of insect pests mainly in horticultural crops

Ejemplos de plagas controladas: Ants, Beetles, Cockroaches, Fleas, Termites, Thrips, Black vine weevil and other insects

Ejemplos de aplicaciones: Hardy ornamentals; Non-edible ornamentals; Turf

Eficacia y actividad: Effective as an antiparasitic although there is growing and historic evidence of resistance in fleas. Research has shown that fipronil appeared to be a very effective alternative to existing substances in stored-grain protection however, it is not approved for such uses in the EU.

Availability status: Current

Introduction & key dates: 1987, discovered; 1992, first reported

CEE Regulación 1107/2009 ( 91/414):

Estado	Not approved
Dossier rapporteur/co-rapporteur	France
Date inclusion expires	No aplicable
UE Candidatas a sustitución	-
Incluido en la base de datos de la UE	Sí

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, Estados Unidos

Estructura química:

Isomerism	A chiral molecule, fipronil is an isomeric mixture of two enantiomers (+/-; S/R)
Fórmula química	C12H4Cl2F6N4OS
Canonical SMILES	C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)C(F)(F)F)N)Cl)C(F)(F)F
Isomeric SMILES	No data
International Chemical Identifier Key (InChIKey)	ZOCSXAVNDGMNBV-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2
¿Diagrama de estructura 2D / imagen disponible?	Sí

Cambridge Crystallographic Data Centre diagrams:

Nombre Común	Relación	Vínculo
Fipronil	Unstated isomer

Estado general:

Tipo de pesticida	Insecticide, Veterinary substance
Grupo químico	Phenylpyrazole
Minimum active substance purity	950 +/- 25 g/kg
Known relevant impurities	EU dossier - None declared
Sustancias de origen	Sintéticas
Modo de acción	Broad-spectrum with contact and stomach action. GABA-gated chloride channel antagonist.
CAS RN	120068-37-3
CEE número	424-610-5
Número CIPAC	581
EPA américaine chimiques de code	129121
PubChem CID	3352
Masa molecular (g mol-1)	437.15
PIN (Preferred Identification Name)	5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethanesulfinyl)-1H-pyrazole-3-carbonitrile
Nombre IUPAC	5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile
Nombre CAS	5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile
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)	2B
Fungicide Resistance Classification (FRAC)	No aplicable
Examples of recorded resistance	Frankliniella occidentalis Sogatella furcifera Spodoptera litura Blattella germanica Chilo suppressalis Musca domestica many others
Estado físico	White powder
Related substances & organisms	-

Formulaciones:

Propiedad	Valor
Example manufacturers & suppliers of products using this active now or historically	BASF Certis Bayer Kingtai Chemicals
Example products using this active	Goliath Gel Vi-Nil Regent 500FS Regency Sofion
Estado de UK LERAP	None
Formulation and application details	Often supplied as fine granules which are dissolved in water and used as a seed or compost treatment for crop applications, and as cutaneous sprays and spot-on liquids for animal use.

DESTINO AMBIENTAL
for fipronil

Propiedad		Valor	Fuente/Cuenta de Cualidad/Otra Información	Interpretación
Solubilidad - En aqua en 20oC (mg l-1)		3.78	A5	Bajo
Solubilidad - en solventes organicos en 20oC (mg l-1)		28	A5 - Hexano	-
		3000	A5 - Tolueno	-
		137500	A5 - Metanol	-
		545900	A5 - Acetona	-
Punto de fusión (oC)		203	A5	-
Punto de ebullición (oC)		Decomposes before boiling	A5	-
El punto de degradación (oC)		230	A5	-
Punto de inflamación (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-aqua coeficiente de particiónat en pH 7, 20oC	P	5.62 X 1003	Calculado	-
	Log P	3.75	A5	Alto
Masa densidad (g ml-1)/Peso específico		1.71	A5	-
Disociación constante (pKa) at 25oC		No aplicable	A5	-
		Nota: Ninguna disociación
Presión de vapor en 20oC (mPa)		0.002	A5	Baja volatilidad
Constante de Henry a 25oC (Pa m3 mol-1)		2.31 X 10-04	A5	No volátil
Indice de potencial de lixiviación GUS		2.45	Calculado	Estado de transición
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Valor	1.55 X 10-01	Calculado	-
	Nota	-
Potencial para transportar de 'particle bound'		-	Calculado	Mediano
Maximum UV-vis absorption L mol-1 cm-1		203nm = 48385, 286nm = 7281, 291nm = 6008	A5	-
Surface tension (mN m-1)		72.5	A5 at 20oC	-

Degradación:

Propiedad		Valor	Fuente/Cuenta de Cualidad/Otra Información	Interpretación
Biodegradabilidad general		-
Degradación de suelo (días) (aerobic)	DT50 (típico)	142	A5	Persistente
	DT50 (laboratorio en 20oC)	142	A5	Persistente
	DT50 (campo)	65	A5	Persistente moderado
	DT90 (laboratorio en 20oC)	-	-	-
	DT90 (campo)	-	-	-
	Endpoint de modelado DT50	-	-	-
	Nota	EU dossier lab studies DT50 range 32-346 days, geometric mean 142, field studies range 5.6-135 days 4 European sites; Other sources: 96 days (DW4)
Dissipation rate RL50 on plant matrix	Valor	3.3	R3	-
	Nota	Cabbage leaves, n=1
Dissipation rate RL50 on and in plant matrix	Valor	6.1	R4	-
	Nota	Published literature RL50 range 1.0-14.0 days, 9 field crops, various matrices, n=9
Acuoso fotólisis DT50 (días) en pH 7	Valor	0.33	B5	Rápido
	Nota	Rapid in artifical light
Acuoso hidrólisis DT50 (días) en 20oC y pH 7	Valor	Estable	A5	-
	Nota	Stable pH 5 to pH 7, some hydrolysis occurs at pH 9 - DT50 circa 11 days at 50 degC
Aqua-Sedimento DT50 (días)		68	A5	Moderado rápido
Fase de agua sola DT50 (días)		54	A5	Estable

De absorción del suelo y la movilidad:

Propiedad		Valor	Fuente/Cuenta de Cualidad/Otra Información	Interpretación
Lineal	Kd	-	-	-
	Koc	-
	Notas y rango	-
Freundlich	Kf	11.85	A5	Móvil un poco
	Kfoc	727
	1/n	0.95
	Notas y rango	EU dossier Kf range 4.19-20.7 mL/g, Kfoc range 427-1248 mL/g, Soils=5
pH senbsibilidad		No

Key metabolites:

Metabolito		Medio de formación	Maximó Calculado de Fracción Ocurrencia	1107/2009 Importancia
fipronil amide (Ref: RPA 200766)		Suelo	0.384	Major fraction, Relevant
fipronil sulfone (Ref: MB 46136)		Suelo	0.343	Major fraction, Relevant
fipronil sulfide (Ref: MB 45950)		Suelo	0.170	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Medio de formación / Rate	Maximó Calculado de Fracción Ocurrencia	Metabolising enzymes
5-amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-1H-pyrazole-3-carbonitrile (Ref: MB 45897)	-	Rat	-	-
5-amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-4-trifluoro-methylpyrazole-3-carbonitrile (Ref: MB 46513) Nota: Low mobility	-	Soil (Photolysis, Aerobic); Water; Plant	-	-
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) pyrazole-4-sulfonic acid, potassium (Ref: RPA 104615) Nota: Rat oral LD50 > 2000 mg kg-1 bw	-	Soil (Photolysis); Plant	-	-
1-(2,6-dichloro-4-trifluoromethylphenyl)-3-amino-5-amino-4-trifluoromethylsulfonylpyrazole (Ref: RPA 105048) Nota: Rat oral LD50 467 mg kg-1 bw	-	Water	-	-
5-amino-3-carbamyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-rifluoromethylsulfonylpyrazole (Ref: RPA 105320) Nota: Rat oral LD50 > 2000 mg kg-1 bw	-	Plant	-	-
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole-3-carboxylic acid (Ref: RPA 200761) Nota: Persistent	-	Soil (Aerobic); Plant	-	-

ECOTOXICOLOGÍA
for fipronil

Propiedad		Valor	Fuente/Cuenta de Cualidad/Otra Información	Interpretación
Factor de la bio-concentración	BCF (l kg-1)	321	A5 (Whole fish, Other literature Log BCF range 1.0-1.8 (R3))	Umbral de importancia
	CT50 (días)	3		-
Mamíferos - Agudos oral LD50 (mg kg-1)		92	B5 Rata	Alto
Mamíferos - a corto plazo NOEL	(mg kg-1)	0.35	A5 Rata	Alto
	(ppm dieta)	-		-
Pájaros/aves - Agudos LD50 (mg kg-1)		11.3	B5 Colinus virginianus	Alto
Birds - Short term dietary (LC50/LD50)		-	-	-
Pez - agudo 96 hora LC50 (mg l-1)		0.248	A5 Oncorhynchus mykiss	Moderado
Pez - Crónico 21 días NOEC (mg l-1)		0.015	A5 Oncorhynchus mykiss	Moderado
Invertebrados acuáticos - Agudos 48 hora EC50 (mg l-1)		0.19	B5 Daphnia magna	Moderado
Invertebrados acuáticos - Crónicos 21 días NOEC (mg l-1)		0.068	A5 Daphnia magna	Moderado
Crustáceos acuáticos - Agudos 96 hora LC50 (mg l-1)		0.00014	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)		0.0001	A5 Chironomus riparius	Alto
Sediment dwelling organisms - Crónicos 28 día NOEC, sedimento (mg kg-1)		0.0002	A5 Chironomus riparius	Alto
Plantas acuáticas - Agudos 7 día EC50, biomasa (mg l-1)		0.16	A5 Lemna gibba	Moderado
Non-target plants		-	-	-
		-	-	-
Algas - Agudos 72 hora EC50, crecimiento (mg l-1)		0.068	A5 Scenedemus subspicatus	Moderado
Algas - Crónicos 96 hora NOEC, crecimiento (mg l-1)		-	-	-
Abejas mielíferas	Contacto aguda 48 hora LD50 (μg abeja-1)	0.0059	A5	Alto
	Oral aguda 48 hora LD50 (μg abeja-1)	0.00417	A5 Apis mellifera	Alto
	Modo desconocido aguda 48 hora LD50 (μg abeja-1)	-	-	-
Lombrices - Agudos 14 día LC50 (mg kg-1)		> 500	A5 Eisenia foetida, corr	Moderado
Lombrices - Crónicos 14 día NOEC, reproducción (mg kg-1)		500	A5 Eisenia foetida, corr	Bajo
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Causalidad	0.32	A5 Folsomia candida, EC50 Reproduction mg kg-1	-
Otro arthropoda (1)	LR50 g ha-1	0.01	48 hora A5 Aphidius rhopalosiphi, adult	-
	% Causalidad	-	-	-
Otro arthropoda (2)	LR50 g ha-1	0.101	7 día A5 Typhlodromus pyri	-
	% Causalidad	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 0.67 mg kg-1 soil, 28 días	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

LA SALUD HUMANA Y PROTECCIÓN
for fipronil

General:

Propiedad		Valor	Fuente/Cuenta de Cualidad/Otra Información	Interpretación
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mamíferos - Agudos oral LD50 (mg kg-1)		92	B5 Rata	Alto
Mammals - Dermal LD50 (mg kg-1 body weight)		354	A5 Rabbit	-
Mammals - Inhalation LC50 (mg l-1)		0.36	A5 Rat	-
Other Mammal toxicity endpoints		-		-
Consumo cada día aceptable (mg kg-1p.c. días-1)		0.0002	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1p.c. días-1)		0.009	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)		0.0035	A5 Dog, SF=100	-
Estudios den la absorción cutánea (%)		1.0	A5	-
Directivo 76/464 Sustancias Peligrosas		Lista II	-	-
Limites de exposiciones		-	-	-
Exposure Routes	Public	Negligible risk to bystanders as pesticide as normally used as seed treatment
	Occupational	Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

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		Thyroid, kidney and liver toxicant Highly toxic Bioaccumulates 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		Valor	Fuente/Cuenta de Cualidad/Otra Información	Interpretación
General		Not explosive IMDG Transport Code is usually 6.1
CLP classification 2013		Health: H301, H311, H331, H372 Environment: H400, H10
CEE clasificación de riesgos		T - Toxic: R23/24/25, R48/25 N - Dangerous for the environment: R50, R53
CEE clasificación sin riesgos		S1/2, S28, S36/37, S45, S60, S61
Clasificación de OSM		II	-	Peligroso mediano
US EPA Classification (formulation)		II	-	Warning - Moderately toxic
Número de las NU		2588
Waste disposal & packaging		Packaging Group III (minor danger)

TRADUCCIONES
for fipronil

Idioma	Nombre
Inglés	fipronil
Francés	fipronil
Alemán	Fipronil
Danés	fipronil
Italiano	fipronil
Español	fipronil
Griego	-
Esloveno	fipronil
Polaco	fipronil
Sueco	-
Húngaro	fipronil
Holandés	fipronil

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Última actualización del registro: Wednesday 31 October 2018
Contacto: aeru@herts.ac.uk