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Captafol (Ref: Ortho-5865)
Last updated: 05/01/2021
(Also known as: captofol; difolatan; merpafol)

SUMMARY
Captafol is a broad spectrum fungicide that is not approved for use in the EU. It has a low aqueous solubility, is non-volatile and, based on its chemical properties, would not normally be expected to leach to groundwater. It is not persistent in soil or water systems. Captafol has a low mammalian toxicity and is not expected to bioaccumulate. It is reported as a carcinogen and irritant. It is moderately toxic to birds, honeybees, earthworms and most aquatic organisms.
GENERAL INFORMATION
Description
A broad-spectrum phthalimide, contact fungicide often used to control diseases of fruit and other crops
Example pests controlled
Foliage and fruit fungal diseases
Example applications
Fruit including apples, citrus, cranberry, blueberry, prunes, stone fruit; Potatoes; Tomatoes; Coffee; Peanuts; Onions;
Efficacy & activity
-
Availability status
Unknown
Introduction & key dates
circa 1962
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Expired/Banned
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
-
Date EC 1107/2009 inclusion expires
Expired/Banned
EU Candidate for substitution (CfS)
-
Listed in EU database
Yes
Approved for use (✓) under EC 1107/2009 in the following EU Member States
ATAustria
BEBelgium
BGBulgaria
CYCyprus
CZCzech Republic
DEGermany
DKDenmark
EEEstonia
ELGreece
                 
ESSpain
FIFinland
FRFrance
HRCroatia
HUHungary
IEIreland
ITItaly
LTLithuania
LULuxembourg
                 
LVLatvia
MTMalta
NLNetherlands
PLPoland
PTPortugal
RORomania
SESweden
SISlovenia
SKSlovakia
                 
Also used in
Also used in
-
Chemical structure
Isomerism
A chiral molecule, an isomeric mixture
Chemical formula
C₁₀H₉Cl₄NO₂S
Canonical SMILES
C1C=CCC2C1C(=O)N(C2=O)SC(C(Cl)Cl)(Cl)Cl
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
JHRWWRDRBPCWTF-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C10H9Cl4NO2S/c11-9(12)10(13,14)18-15-7(16)5-3-1-2-4-6(5)8(15)17/h1-2,5-6,9H,3-4H2
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
captafol Unstated isomer
General status
Pesticide type
Fungicide
Substance group
Phthalimide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Acts by inhibiting the germination of spores. Multi-site activity.
CAS RN
2425-06-1
EC number
219-363-3
CIPAC number
185
US EPA chemical code
081701
PubChem CID
17038
CLP index number
613-046-00-7
Molecular mass
349.06
PIN (Preferred Identification Name)
2-[(1,1,2,2-tetrachloroethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
IUPAC name
N-(1,1,2,2-tetrachloroethylthio)cyclohex-4-ene-1,2-dicarboximide
CAS name
3a,4,7,7a-tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-1H-isoindole-1,3(2H)-dione
Other status information
Chemical subject to PIC regulations; Rotterdam Convention (Class Ia)
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)
M04
Examples of recorded resistance
-
Physical state
Colourless/yellow crystals
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Merpafol
  • Crisfolatan
  • Folcid
  • Difolatan
  • Haipen
  • Sanspor
Example products using this active
  • Scotts Company
  • Chevron
  • Makhteshim Agan
  • Pillar International
Formulation and application details
Available in a variety of formulations including dusts, wettable powders, aqueous suspensions and suspension concentrates
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
1.4
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
25000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Benzene
-
17000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Toluene
-
100000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Xylene
-
43000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone
-
Melting point (°C)
161
A4 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
4 = Verified data
-
Boiling point (°C)
Decomposes before boiling
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Degradation point (°C)
161
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
6.76 X 1003 Calculated -
Log P
3.83
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
High
Bulk density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
1.30 X 10-09
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
3.30 X 10-01
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Moderately volatile
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
39
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
7.0
DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. MS in preparation
4 = Verified data
Non-persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
FAO state DT₅₀ 23-55 days; Other literature values DT₅₀ range from 2-11 days
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
- - -
Note
-
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Note
Rapidly hydrolysed in acidic and alkaline conditions
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Slightly mobile
Koc
2000
Notes and range
Best available data
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
0.59 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
6.88 X 10-03 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
Potential for loss via drain flow
Slightly mobile Calculated -
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
tetrahydrophthalimidic acid - Animals - -
dichloroactetic acid - Animals - -
phthalic acid - Animals - -
ammonia - Animals - -
tetrahydrophthalimide THPI Animals - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
27
Q2 Q = Miscellaneous internet resources
2 = Unverified data of unknown source
Estimated
Low potential
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5500
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 year
-
(ppm diet)
500 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
101700
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Anas platyrhynchos
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.5
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
> 0.25
J3 J = Pesticide Action Network database (click here )
3 = Unverified data of known source
Cyprinidae 13 day
Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 3.34
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
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)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)
- - -
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
> 96.7
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
72 Hr
Moderate
Bumblebees (Bombus spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Mason bees (Osmia spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Other pollinators (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other pollinators (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
> 351
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Eisenia foetida
Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5500
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
5000
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.72
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
Contact dermatitis, severe irritation of the respiratory tract, eye damage and other systemic effects are reported
European MRLs
EU MRL pesticide database 
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
Yes, known to cause a problem
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
XNo, known not to cause a problem
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
Yes, known to cause a problem
Yes, known to cause a problem
Eye irritant Phototoxicant  
?Possibly, status not identified
No data found  
General human health issues
IARC group 2A carcinogen; USEPA - probable human carcinogen
May cause dermatitis
May cause conjunctivitis and periorbital edema
Handling issues
Property
Value and interpretation
General
Corrosive to metals
Avoid generation of dust
CLP classification 2013
Health: H317, H350
Environment: H400, H410
EC Risk Classification
Carcinogen category 2: R45
Xn - Harmful: R43
N - Dangerous for the environment: R50, R53
EC Safety Classification
S45, S53, S61, S60
WHO Classification
Ia (Extremely hazardous)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
captafol
French
captafole
German
Captafol
Danish
captafol
Italian
captafol
Spanish
captafol
Greek
-
Polish
kaptafol
Swedish
-
Hungarian
-
Dutch
captafol

Record last updated: 05/01/2021
Contact: aeru@herts.ac.uk
Please cite as: Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242