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Endosulfan (Ref: OMS 570)
Last updated: 10/12/2019
(Also known as: thiodan; benzoepin; FMC 5462; ENT 23979; thiosulfan)

SUMMARY
Endosulfan is an insecticide and acaricide that is not approved for use in the EU. It has a low aqueous solubility and is volatile. Based on its chemical properties it may have a tendency to leach to groundwater. Endosulfan is moderately persistent in soil but does not tend to persist in water systems. It is highly toxic to mammals, a neurotoxin and possibly a mutagen. It is moderately toxic to birds, honeybees and earthworms but slightly more toxic to aquatic organisms.
GENERAL INFORMATION
Description
An isomer mixture of alpha- and beta-endosulfan which is an insecticide and acaricide used to control sucking, chewing and boring insects
Example pests controlled
Whiteflies; Aphids; Leafhoppers; Colorado beetle; Cabbage worms; Ticks; Mites; Tstetse flies.
Example applications
Vegetable crops; Cotton; Potatoes; Tomatoes; Apples
Efficacy & activity
-
Availability status
Current
Introduction & key dates
circa 1956
UK regulatory status
UK approval status
Not approved
EC Regulation 1107/2009 (repealing 91/414)
EC Directive 91/414 Status
Not approved
Dossier rapporteur/co-rapporteur
Spain
Date inclusion expires
Expired
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
Yes
Approved for use (✓) or known to be used (#) in the following EU-27 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
Australia, USA
Chemical structure
Isomerism
A molecule with 4 chiral centres, endosulfan is is a mixture of the alpha- and beta-forms.
Chemical formula
C₉H₆Cl₆O₃S
Canonical SMILES
C1C2C(COS(=O)O1)C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl
Isomeric SMILES
C1[C@@H]2[C@H](COS(=O)O1)[C@@]3(C(=C([C@]2(C3(Cl)Cl)Cl)Cl)Cl)Cl
International Chemical Identifier key (InChIKey)
RDYMFSUJUZBWLH-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C9H6Cl6O3S/c10-5-6(11)8(13)4-2-18-19(16)17-1-3(4)7(5,12)9(8,14)15/h3-4H,1-2H2
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
endosulfan Beta-isomer
General status
Pesticide type
Insecticide, Acaricide
Substance group
Organochlorine
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic with contact and stomach action, acts as a non-competitive GABA antagonist
CAS RN
115-29-7
EC number
204-079-4
CIPAC number
89
US EPA chemical code
079401
PubChem CID
3224
Molecular mass
406.93
PIN (Preferred Identification Name)
(5aE,6E,9E,9aE)-6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-one
IUPAC name
1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene sulfite
CAS name
6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin 3-oxide
Other status information
POP - regulated by Stockholm Convention; OSPAR pfa/soc; WFD priority substance; Severe Marine Pollutant; Global ban (2011); Chemical subject to PIC regulation
Relevant Environmental Water Quality Standards
EU Directive 2008/105/EC EQS surface waters: annual average 0.005 µg l⁻¹; max measured 0.01 µg l⁻¹
UK Statutory standard for the protection of aquatic life in inland waters, coastal and territorial waters: 0.003 µg l⁻¹ as annual average
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
2A
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
Many recorded cases, Aphis gossypii, Bemisia tabaci, Dasineura tetensi, Leptinotarsa decemlineata, Myzus persicae, many others
Physical state
Colourless to brown coloured crystals
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Thiodan
  • Benzoepin
Example products using this active
  • Bayer CropScience
  • Hoechst
  • FMC
  • Velsicol
  • Makhteshim-Agan
UK LERAP status
No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details
Supplied in a variety of formulations including emulsifiable concentrates, wettable powders, granules and dusts
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.32
H4 H = The US ARS pesticide properties database (click here )
4 = Verified data
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
200000
C4 C = AGRITOX (click here )
4 = Verified data
Ethyl acetate
-
65000
C4 C = AGRITOX (click here )
4 = Verified data
Ethanol
-
24000
C4 C = AGRITOX (click here )
4 = Verified data
Hexane
-
200000
C4 C = AGRITOX (click here )
4 = Verified data
Toluene
-
Melting point (°C)
80
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
5.62 X 1004 Calculated -
Log P
4.75
E4 E = Manufacturers safety data sheets
4 = Verified data
High
Bulk density (g ml⁻¹)
1.8
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
0.83
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
1.48
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Moderately volatile
GUS leaching potential index
5.28 Calculated High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
5.86 X 1000 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
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)
50
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Moderately persistent
DT₅₀ (lab at 20 °C)
39
A5 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 )
5 = Verified data used for regulatory purposes
Moderately persistent
DT₅₀ (field)
86
A5 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 )
5 = Verified data used for regulatory purposes
Moderately persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
EU dossier lab studies DT₅₀ range 28-50 days, field studies DT₅₀ range 62-126 days for summer applications, 68-87 days for autumn applications (UK); FAO state DT₅₀ 60-800 days
Dissipation rate RL₅₀ on plant matrix
Value
3.7
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
Published literature RL₅₀ range 0.1-5.5 days, 19 field crops, various matrices, n=23
Dissipation rate RL₅₀ on and in plant matrix
Value
4.3
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
Published literature RL₅₀ range 0.4-14.5 days, 19 field & undercover grown crops, various matrices, n=41
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
20
C4 C = AGRITOX (click here )
4 = Verified data
Non-persistent
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Non-mobile
Koc
11500
Notes and range
-
Freundlich
Kf
0.28
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Mobile
Kfoc
18.6
1/n
0.558
Notes and range
Literature data Kf range 0.08-0.52 mL g⁻¹, Kfoc range 5.7-38.5 mL g⁻¹, 1/n range 0.500-0.648, soils=4
pH sensitivity
-
Key metabolites
Metabolite
Formation medium
Estimated maximum occurrence fraction
1107/2009 relevancy
endosulfan sulfate
Soil - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
2755
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
(Whole fish Literature values log BCF range 1.0-3.7 (R3))
Threshold for concern
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
38
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
High
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)
15 -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 111
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Anas platyrhynchos
Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.002
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
Oncorhynchus mykiss
High
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.0000005
P4 P = Other governments and regulators
4 = Verified data
Cyprinodon variegatus 28 day
High
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.44
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
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
0.24
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
Americamysis bahia
Moderate
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)
0.1
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
Chironomus riparius 2 day
Moderate
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)
2.15
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
Anabaena doliolum
Moderate
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)
> 7.81
C4 C = AGRITOX (click here )
4 = Verified data
Apis mellifera
Moderate
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
> 15.6
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
Apis mellifera 24hr
Moderate
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
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)
> 1.72
R4 R = Peer reviewed scientific publications
4 = Verified data
Bombus terrestris
Moderate
-
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)
0.210
R4 R = Peer reviewed scientific publications
4 = Verified data
Trigona spinipes
High
Mode of exposure
Contact
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)
> 14
C4 C = AGRITOX (click here )
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
Harmless
AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005
2 = Unverified data of unknown source
Chrysoperla carnea
-
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)
38
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
500
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.013
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)
0.006
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
JMPR 1998
-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.02
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
JMPR 1998
-
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
List II - -
Exposure Routes
Public
-
Occupational
-
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
XNo, known not to cause a problem
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
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
;
E1 E = Unspecified genotoxicity type (miscellaneous data source)
1 = Positive
?Possibly, status not identified
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
Yes, known to cause a problem
XNo, known not to cause a problem
Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found No data found No data found
Eye irritant Phototoxicant  
No data found No data found  
General human health issues
Mutagenic potential
Highly toxic
Research shows that endosulfan interferes with the spermatogenic & steroidogenic cycles in rats
Endocrine issues - Competitive binding to androgen receptors
Handling issues
Property
Value and interpretation
General
Corrosive
IMDG Transport Code is usually 6.1
CLP classification 2013
Health: H300, H312, H330
Environment: H400, H410
EC Risk Classification
T+ - Very toxic: R26/28
Xn - Harmful: R21
N - Dangerous for the environment: R50, R53
EC Safety Classification
S1/2, S28, S36/37, S45, S60, S61, S63
WHO Classification
II (Moderately hazardous)
UN Number
2761
Waste disposal & packaging
Packaging Group II (medium danger)
TRANSLATIONS
Language
Name
English
endosulfan
French
endosulfan
German
Endosulfan
Danish
endosulfan
Italian
endosulfan
Spanish
endosulfan
Greek
endosulphan
Polish
endosulfan
Swedish
-
Hungarian
endoszulfan
Dutch
endosulfan

Record last updated: 10/12/2019
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