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PhD Oportunity with Syngenta & the University of Hertfordshire

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

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
Further data may be found in the VSDB

SUMMARY

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.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for fipronil

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

Example pests controlled: Ants, Beetles, Cockroaches, Fleas, Termites, Thrips, Black vine weevil and other insects

Example applications: Hardy ornamentals; Non-edible ornamentals; Turf

Efficacy & activity: 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

EC Regulation 1107/2009 (repealing 91/414):
Status Not approved
Dossier rapporteur/co-rapporteur France
Date inclusion expires Not applicable
EU Candidate for substitution (CfS) -
Listed in EU database Yes

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, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A chiral molecule, fipronil is an isomeric mixture of two enantiomers (+/-; S/R)
Chemical formula 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
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Insecticide, Veterinary substance
Substance group Phenylpyrazole
Minimum active substance purity 950 +/- 25 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Broad-spectrum with contact and stomach action. GABA-gated chloride channel antagonist.
CAS RN 120068-37-3
EC number 424-610-5
CIPAC number 581
US EPA chemical code 129121
PubChem CID 3352
Molecular mass (g mol-1) 437.15
PIN (Preferred Identification Name) 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethanesulfinyl)-1H-pyrazole-3-carbonitrile
IUPAC name 5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile
CAS name 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) 2B
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Frankliniella occidentalis
Sogatella furcifera
Spodoptera litura
Blattella germanica
Chilo suppressalis
Musca domestica
many others
Physical state White powder
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site Value
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
UK LERAP status 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.


ENVIRONMENTAL FATE

for fipronil

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 3.78 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 28 A5 - Hexane -
3000 A5 - Toluene -
137500 A5 - Methanol -
545900 A5 - Acetone -
Melting point (oC) 203 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 230 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 5.62 X 1003 Calculated -
Log P 3.75 A5 High
Bulk density (g ml-1)/Specific gravity 1.71 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.002 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 2.31 X 10-04 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 2.45 Calculated Transition state
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 Value 1.55 X 10-01 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
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 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 142 A5 Persistent
DT50 (lab at 20oC) 142 A5 Persistent
DT50 (field) 65 A5 Moderately persistent
DT90 (lab at 20oC) - - -
DT90 (field) - - -
DT50 modelling endpoint - - -
Note 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 Value 3.3 R3 -
Note Cabbage leaves, n=1
Dissipation rate RL50 on and in plant matrix Value 6.1 R4 -
Note Published literature RL50 range 1.0-14.0 days, 9 field crops, various matrices, n=9
Aqueous photolysis DT50 (days) at pH 7 Value 0.33 B5 Fast
Note Rapid in artifical light
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 7, some hydrolysis occurs at pH 9 - DT50 circa 11 days at 50 degC
Water-sediment DT50 (days) 68 A5 Moderately fast
Water phase only DT50 (days) 54 A5 Stable

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 11.85 A5 Slightly mobile
Kfoc 727
1/n 0.95
Notes and range EU dossier Kf range 4.19-20.7 mL/g, Kfoc range 427-1248 mL/g, Soils=5
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
fipronil amide (Ref: RPA 200766) This metabolite may cause environmental pollution, click here for further information Soil   0.384   Major fraction, Relevant
fipronil sulfone (Ref: MB 46136) This metabolite may cause environmental pollution, click here for further information Soil   0.343   Major fraction, Relevant
fipronil sulfide (Ref: MB 45950) This metabolite may cause environmental pollution, click here for further information Soil   0.170   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction 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)
Note: 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)
Note: 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)
Note: Rat oral LD50 467 mg kg-1 bw
- Water - -
5-amino-3-carbamyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-rifluoromethylsulfonylpyrazole
(Ref: RPA 105320)
Note: 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)
Note: Persistent
- Soil (Aerobic); Plant - -


ECOTOXICOLOGY

for fipronil

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 321 A5 (Whole fish, Other literature Log BCF range 1.0-1.8 (R3)) Threshold for concern
CT50 (days) 3 -
Mammals - Acute oral LD50 (mg kg-1) 92 B5 Rat High
Mammals - Short term dietary NOEL (mg kg-1) 0.35 A5 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) 11.3 B5 Colinus virginianus High
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.248 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.015 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.19 B5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.068 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.00014 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) 0.0001 A5 Chironomus riparius High
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) 0.0002 A5 Chironomus riparius High
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.16 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.068 A5 Scenedemus subspicatus Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) 0.0059 A5 High
Oral acute 48 hour LD50 (μg bee-1) 0.00417 A5 Apis mellifera High
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 500 A5 Eisenia foetida, corr Low
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect 0.32 A5 Folsomia candida, EC50 Reproduction mg kg-1 -
Other arthropod (1) LR50 g ha-1 0.01 48 hour
A5 Aphidius rhopalosiphi, adult
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 0.101 7 day
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.67 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for fipronil

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation 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) - -
Mammals - Acute oral LD50 (mg kg-1) 92 B5 Rat High
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 - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.0002 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.009 A5 Rat, 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) 0.0035 A5 Dog, SF=100 -
Dermal penetration studies (%) 1.0 A5 -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
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 Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

General human health issues 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:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation 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
IMDG Transport Code is usually 6.1
CLP classification 2013 Health: H301, H311, H331, H372
Environment: H400, H10
EC Risk Classification Click here to view information omn the EU risk phrases T - Toxic: R23/24/25, R48/25
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S1/2, S28, S36/37, S45, S60, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II - Warning - Moderately toxic
UN Number 2588
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for fipronil

Language Name
English fipronil
French fipronil
German Fipronil
Danish fipronil
Italian fipronil
Spanish fipronil
Greek -
Slovenian fipronil
Polish fipronil
Swedish -
Hungarian fipronil
Dutch fipronil

Record last updated: Thursday 07 June 2018
Contact: aeru@herts.ac.uk