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endosulfan (Ref: OMS 570)
** thiodan ** benzoepin ** FMC 5462 ** ENT 23979 ** thiosulfan ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

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 Click here for an explantaion of the general chemical status information
for endosulfan

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

EC Regulation 1107/2009 (repealing 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 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 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

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Endosulfan Beta-isomer Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
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 (g mol-1) 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 ug/L; max measured 0.01 ug/L
UK Statutory standard for the protection of aquatic life in inland waters, coastal and territorial waters: 0.003 ug/L 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
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
  • Hoechst
  • FMC
  • Velsicol
  • Makhteshim-Agan
Example products using this active
  • Thiodan
  • Benzoepin
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

for endosulfan

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) 0.32 H4 Low
Solubility - In organic solvents at 20oC (mg l-1) 200000 C4 - Ethyl acetate -
65000 C4 - Ethanol -
24000 C4 - Hexane -
200000 C4 - Toluene -
Melting point (oC) 80 L3 -
Boiling point (oC) - - -
Degradation point (oC) - - -
Flashpoint (oC) - - -
Octanol-water partition coefficient at pH 7, 20oC P 5.62 X 1004 Calculated -
Log P 4.75 E4 High
Bulk density (g ml-1)/Specific gravity 1.8 L3 -
Dissociation constant (pKa) at 25oC - - -
Note:
Vapour pressure at 20oC (mPa) 0.83 L3 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.48 L3 Moderately volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 4.34 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 1.46 X 10+00 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 - - -
Surface tension (mN m-1) - - -

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) 50 L3 Moderately persistent
DT50 (lab at 20oC) 39 A5 Moderately persistent
DT50 (field) 86 A5 Moderately persistent
DT90 (lab at 20oC) - - -
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 -
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 -
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 20oC and pH 7 Value 20 C4 Non-persistent
Note -
Water-sediment DT50 (days) - - -
Water phase only DT50 (days) - - -

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 - L3 Non-mobile
Koc 11500
Notes and range -
Freundlich Kf 0.28 R3 Mobile
Kfoc 18.6
1/n 0.558
Notes and range Literature data Kf range 0.08-0.52 mL/g, Kfoc range 5.7-38.5 mL/g, 1/n range 0.500-0.648, soils=4
pH sensitivity -

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
endosulfan sulfate Soil   -   -


ECOTOXICOLOGY

for endosulfan

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) 2755 F4 (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 Rat High
Mammals - Short term dietary NOEL (mg kg-1) - L2 Rat, 2 year -
(ppm diet) 15 -
Birds - Acute LD50 (mg kg-1) > 111 L3 Anas platyrhynchos Moderate
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.002 F4 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.0000001 Q1 Oncorhynchus mykiss, 28 day High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.44 F4 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) - - -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.24 F4 Americamysis bahia Moderate
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) 0.1 F3 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 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 Apis mellifera Moderate
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 15.6 F3 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 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 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 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect Harmless AA2 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

for endosulfan

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) 38 L3 Rat High
Mammals - Dermal LD50 (mg kg-1 body weight) > 500 R3 Rat -
Mammals - Inhalation LC50 (mg l-1) 0.013 L3 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.006 JMPR 1998 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.02 JMPR 1998 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) - - -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 List II - -
Exposure Routes Public -
Occupational -
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A3; B0; C0; D0; E1

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

-

-

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
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: 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 Corrosive
IMDG Transport Code is usually 6.1
CLP classification 2013 Health: H300, H312, H330
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases T+ - Very toxic: R26/28
Xn - Harmful: R21
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, S63
WHO Classification II - Moderately hazardous
UN Number 2761
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group II (medium danger)


TRANSLATIONS

for endosulfan

Language Name
English endosulfan
French endosulfan
German Endosulfan
Danish endosulfan
Italian endosulfan
Spanish endosulfan
Greek endosulphan
Slovenian endosulfan
Polish endosulfan
Swedish -
Hungarian endoszulfan
Dutch endosulfan

Record last updated: Thursday 20 June 2019
Contact: aeru@herts.ac.uk