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fluopicolide (Ref: AE C638206)
** Translations

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

Description: A fungicide used for the control of a range of Oomycete diseases including downy mildew and blight

Example pests controlled: Various Oomycete diseases including downy mildews (Plasmopara, Pseudoperonospara, Peronospora, Bremia), late blight (Phytophthora), and some Pythium species.

Example applications: Grapes; Hops; Potatoes; Various vegetables including onions, roots and tubers

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 2006

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK/Spain
Date inclusion expires 31/05/2023
EU Candidate for substitution (CfS) Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C14H8Cl3F3N2O
Canonical SMILES C1=CC(=C(C(=C1)Cl)C(=O)NCC2=C(C=C(C=N2)C(F)(F)F)Cl)Cl
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) GBOYJIHYACSLGN-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C14H8Cl3F3N2O/c15-8-2-1-3-9(16)12(8)13(23)22-6-11-10(17)4-7(5-21-11)14(18,19)20/h1-5H,6H2,(H,22,23)/f/h22H
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Benzamide
Minimum active substance purity 970 g/kg
Known relevant impurities EU dossier - toluene max 0.3%
Substance origin Synthetic
Mode of action Protectant, novel mode of action as fluopicolide delocalises spectrin-like proteins
CAS RN 239110-15-7
EC number -
CIPAC number 787
US EPA chemical code 027412
PubChem CID 11159021
Molecular mass (g mol-1) 383.58
PIN (Preferred Identification Name) -
IUPAC name 2,6-dichloro-N-[3-chloro-5-(trifluoromethyl)-2-pyridylmethyl]benzamide
CAS name 2,6-dichloro-N-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)methyl)benzamide
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) 43
Examples of recorded resistance -
Physical state Beige coloured solid
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
  • Bayer CropScience
Example products using this active
  • Infinito
UK LERAP status None
Formulation and application details Available as dispersible granules that are mixed with water and used as a spray.


ENVIRONMENTAL FATE

for fluopicolide

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) 2.8 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 200 A5 - n-Hexane -
19200 A5 - Ethanol -
20500 A5 - Toluene -
74700 A5 - Acetone -
Melting point (oC) 150 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 320 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 7.94 X 1002 Calculated -
Log P 2.9 A5 Moderate
Bulk density (g ml-1)/Specific gravity 1.65 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 3.03 X 10-04 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 4.15 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 3.63 Calculated High leachability
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 8.10 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 Neutral solution 203nm = 44519, 271nm = 3601 A5 -
Surface tension (mN m-1) 71.3 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) 271 A5 Persistent
DT50 (lab at 20oC) 271 A5 Persistent
DT50 (field) 138.8 A5 Persistent
DT90 (lab at 20oC) 900 A5 -
DT90 (field) 720 A5 -
DT50 modelling endpoint - - -
Note EU dossier Lab studies DT50 range 194-333 days, DT90 range 644-2216 days; Field studies DT50 range 50-172 days, DT90 range 863-1184 days
Dissipation rate RL50 on plant matrix Value 4.3 R3 -
Note Cabbage leaves, n=1
Dissipation rate RL50 on and in plant matrix Value 7.4 R4 -
Note Published literature RL50 range 3.6-11.3 days, 2 field crops, various matrices, n=2
Aqueous photolysis DT50 (days) at pH 7 Value 64 A4 Stable
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Not pH sensitive
Water-sediment DT50 (days) 1117 A5 Stable
Water phase only DT50 (days) 91.4 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 4.20 A5 Moderately mobile
Kfoc 321.1
1/n 0.90
Notes and range EU dossier Kf range 1.42-9.27, Kfoc range 172-580 mL/g, 1/n range 0.86-0.93, Soils=8
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
4-N-[3-chloro-5-trifluoromethyl-pyridin-2-yl-(hydroxyl)methyl]-2,6-dichlorobenzamide (Ref: AE-0608000) This metabolite may cause environmental pollution, click here for further information Soil   0.106   Major fraction, Relevant
2,6-dichlorobenzamide (Ref: AE C653711) This metabolite may cause environmental pollution, click here for further information Soil   0.250   Major fraction, Relevant
3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid (Ref: AE-C657188) Soil   0.073   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
2,6-dichloro-N-[(3-chloro-5-trifluoromethylpyridin-2-yl)methyl]-4-hydroxy benzamide
(Ref: AE 0712556)
- Animal - -
3-methylsulfinyl-5-trifluoro-methylpyridine-2-carboxylic acid
(Ref: AE 1344122)
- Plant; Soil; Groundwater - -
3-sulfo-5-trifluoromethylpyridine-2-carboxylic acid
(Ref: AE 1344123)
- Groundwater; Soil - -
3-mesyl-5-(trifluoromethyl)pyridin-2-ol
(Ref: AE 1388273)
- Soil; Groundwater - -
3,5-dichloro-4-[3-chloro-5-trifluoromethylpyridine-2-yl-methyl) carbamoyl] benzenesulfonic acid
(Ref: AE 1413903)
- Soil; Groundwater - -
3-chloro-2-hydroxy-5-trifluoromethylpyridine
(Ref: AE B102859)
- Plant - -
2,6-dichloro-N-((3-chloro-5-trifluoromethylpyridine-2-yl)methyl)-3-hydroxybenzamide
(Ref: AE C643890)
- Plant; Animal - -
3-chloro-5-trifluoromethylpyridine-2-carboxamide
(Ref: AE C653598)
- Plant; Groundwater - -
2,6-dichloro-3-hydroxybenzamide
(Ref: AE C657378)
- Plant; Rat - -


ECOTOXICOLOGY

for fluopicolide

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) 121 A5 Threshold for concern
CT50 (days) 0.51 -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 10 A3 Rabbit High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2250 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 1744 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 0.36 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.155 A4 Pimephales promelas, 35 day Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 1.8 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.37 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 49.0 A5 Chironomus riparius Low
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) > 3.2 A5 Lemna gibba Moderate
Non-target plants > 3000 A5 Lettuce, Cucumber
Seedling emergence, ER50
as g/ha
-
> 3000 A5 OSR
Vegetative vigour, ER50
as G/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 0.029 A5 Navicula pelliculosa, Biomass Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 241 A5 Low
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) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect 31.25 A5 Folsomia candida, 28 day NOEC -
Other arthropod (1) LR50 g ha-1 8230 48 hour
A5 Aphidius rhopalosiphi
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 7130 7 day
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 1.84 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for fluopicolide

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) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.16 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.08 A3 proposed, Mouse, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.18 A3 proposed 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) 0.05 A3 proposed Rat, 90 day, SF=100 -
Dermal penetration studies (%) 0.24-2.75 A5 concentration dependent -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public No unacceptable risks for bystanders identified
Occupational Potential risk to operators if PPE/PPC not utilised
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=0.24 μg l-1; A5 -

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 Possible liver, kidney and spleen toxicant

: 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 flammable, explosive or oxidising
CLP classification 2013 Environment: H400
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R50, 53
EC Safety Classification Click here to view information omn the EU safety phrases S35, S57
WHO Classification NL - Not listed
US EPA Classification (formulation) No consensus across products or no products available - -
UN Number Usually 3077
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for fluopicolide

Language Name
English fluopicolide
French fluopicolide
German Fluopicolid
Danish fluopicolid
Italian fluopicolide
Spanish fluopicolida
Greek -
Slovenian flupokolid
Polish fluopikolid
Swedish fluopikolid
Hungarian -
Dutch fluopicolide

Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk
© University of Hertfordshire