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

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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

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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