Draft Version: Final Draft (No Previous Version)

Fact sheets on production, use and release of priority substances in the WFD Royal Haskoning Endrin, Final draft For official use only Draft version: Final draft (no previous version)

Status date: 30 September 2002

Comments: - Changed format - Remarks of EU letter ENV B.1/PMM/JD’E/ipD (2002) 310893 (30-702) incorporated - Measures added

SUBSTANCE: Endrin

I Chemical identity

CAS number: 72-20-8

Chemical group: drins

Molecular Formula: C12H8Cl6O

Homologues: not relevant

Synonyms: Endrex, Experimental Insecticide 269, Hexadrin, Nendrin, NCI-COO157, ENT17251, OMS 197, Mendrin [IPCS, 1992]

Technical mixtures: not relevant

II Physical properties

Water solubility: Practically insoluble (0.23 mg/litre at 25°C) [IPCS, 1992]

Vapour pressure: 2.7 x 10-7 mmHg at 25°C (36 Pa at 25°C) [IPCS, 1992]

Log Kow: 5 [EaSI-View 10.0]

III Production and use in 15 EU member states and accession states

1. Way of production/Process description:

Endrin is produced by condensing vinyl chloride with hexachlorocyclopentadiene, dehydrochlorinating the adduct, and subsequent reaction with cyclopentadiene to form isodrin, which is epoxidized by peracetic or perbenzoic acid (Weston, 1964). The intermediate isodrin can be manufactured via 1,2,3,4,7,7-hexachloronorbornadiene (US EPA, 1985) [IPCS, 1992]

2. Fields of application:

Identified uses of endrin are [Brown et al, 2000]: - As an insecticide to protect crops including cotton and grains; - As a rodenticide for mice and vole control; - As an avicide.

3. Production volume:

No estimates of former manufacture in the EU, or of potential current manufacture outside EU, have been indentified during this study [Brown et al, 2000].

4. Number of production sites and locations of production:

Endrin is no longer manufactured in the EU. Former manufacturers were [Tomlin, 1997 in Brown et al, 2000]: - Shell International Chemical Company; - J. Hyman & Co.

5. Use volume:

4K0976.01/O0013/JVS/TL 1 Fact sheets on production, use and release of priority substances in the WFD Royal Haskoning Endrin, Final draft For official use only

Endrin is banned in many countries, including Belgium (1963), Cyprus, Ecuador, Finland, France (1992), Germany (1988), Isreal, Netherlands (1981), Philippines, Portugal (1988), Singapore, Thailand, Togo, UK (1964-1984) [Brown et al, 2000].

6. Relative use volumes in various applications:

Not relevant

7. Existing regulation in member states or associated member states:

European Union Black List, endrin, listed, EC (1982) List I within the framework of Directive 76/464/EEC on pollution caused by certain dangerous substances discharged into the aquatic environment of the Community. Official Journal C 176, 14.7.1982 p. 7 – 10. [EaSI-View 10.0]

UNECE POP & Heavy Metals, Endrin, Listed OPSAR (1998) OSPAR 1998 List of Candidate Substances. OSPAR Strategy with regard to Hazardous Substances (Ref. Nr. 1998-16), Annex 3. Sintra 22-23 July 1998. [EaSI-View 10.0]

The EU prohibited the marketing and use of endrin as a plant protection product in 1988 (79/117/EEC). In addition, there are still community wide limit values for discharges of wastes and water quality objectives in place (88/347/EEC) [Brown et al, 2000].

8. Industrial associations to be addressed:

Not relevant.

IV Releases to environment

1. General way of entrance and schematic picture:

Relevant main routes of release to the environment are given in appendix 1 and summarised as follows:

Point sources: production and formulation plants; transport, storage and handling Diffuse sources: use as rodenticide against mice in orchards, possible contamination by spray-drift, farm wastes, soil- runoff [EURECO, 1990].

2. Atmospheric cycle a. Industrial Point Sources to the air

Not relevant. b. Municipal Collective Sources to the Air:

Release from buildings (Release route: A3) No data available in project database.

Release from waste disposal (release route: A7) No data available in project database. c. Diffuse sources to air and deposition

Deposition from rainfall (release route: S3.3 / S4.3) No data available in project database.

3. Aquatic releases: a. Industrial Point Sources to the aquatic environment:

Production, formulation and industrial use (release route: S8.4/S9) Discharge factor during production was: <0.1 mg/l (at) (total “drins”) NL, 1977 [Arent, 1977 in Eureco, 1990] Discharge during former production and formulation in the total EC was 0.6 t/y (total “drins”) [Water Research Centre, 1987 in Eureco, 1990]

Contamination of surface water by industrial effluents and careless practices and disposal (such as washing of drums and spray equipment in streams) resulted in regional effects [IPCS, 1992].

Release from industrial WWT (release route: S9.2.1)

Relating emission values (or elimination gradient):

Release from WWT/STP (release route S7, S8.4 and S9.2) Relating emission values (or elimination gradient):

Release from waste disposal (release route: S10) Endrin can reach surface water via waste disposal. [IPCS, 1992] c. Diffuse sources to the aquatic environment:

Release from agricultural use The most important route of contamination is surface run-off from soil and crops. Run-off is affected by several complex factors, such as intensity of precipitation, irrigation practices, soil permeability, topographic relief, organic content of the soil, and the degree of vegetative cover. Soils of low permeability and low organic content allow corpious run-off after heavy precipitation [Donoso et al., 1979 in IPCS, 1992]. Another less important source of water contamination is run-off from endrin-coated seeds. Martson et al. (1969) found that although approximately 11% of the initial amount was washed off by water under laboratory conditions, in field conditions the loss was smaller. [IPCS, 1992] A third possible source of contamination is fall-out by precipitation in the form of rain and snow, but the measured levels are negligible. [IPCS, 1992]

Release from traffic and transport Not relevant.

4. Overall Releases and Summary

No quantitative data available in project database about releases due to historical use.

V Environmental fate of releases to environment

1. Adsorption to solids (sediment, sludge, soil):

No data available in project database.

2. Volatilisation:

Volatilisation and photodecomposition are the primary routes for the disappearance of endrin from soil surfaces Endrin can enter the air by volatilisation, evaporation and aerial drift during application, and as a vapour from manufacturing and formulating plants. Most studies showed rapid volatilization following application to soils and crops, the extent of vaporization depending upon a large number of factors, including soil organic matter, moisture content, air humidity, air flow and surface area of plants. [IPCS, 1992]

3. Degradation:

Microbial degradation of endrin depends on presence of an appropriate microbial species and suitable soil conditions; it occurs under anaerobic conditions [Donoso et al., 1979 in IPCS, 1992]. Biodegration is aided by fungi and bacteria as Trichoderma, Pseudomonas, and Baccilus. The major transformation product is delta-ketoendrin [Patil et al., 1970 in IPCS, 1992]. About 150 isolates from various soil samples were screened to investigate the role of these microorganisms in degrading endrin; 25 of the 150 isolates were active. At least seven metabolites were found, but conversion of endrin into ketoendrin was common troughout [Matsumura et al., 1971 in IPCS, 1992].

Biodegration [EaSI-View 10.0] Medium Exposure Exposure Time Degredation 10 mg/l 4 D 99.7 %1) AQ 5 mg/l 7 D 0 %2)

Notes: 1) The relative susceptibility was endrin > aldrin > dieldrin 2) Possible transformation activities by microorganisms in the static-culture-flask studies were not established by the analytical procedures used

4. Partition to compartments:

Endrin sorbs to organic matter in soil and sediment and it accumulates in biota.

5. Behaviour:

Due to low degradation endrin accumulates in the food chain.

VI Evaluation

1. Relevant NOSE-codes of point sources

NOSE-code Sources IPPC-code 107.6Use of pesticides (other than agriculture and forestry) -

2. Evaluation of emission data a. Emission to water

No quantitative data available in project database. Due to legislative controls there are no more emissions from production and formulation sites. b. Emission to air

No quantitative data available in project database. Due to legislative controls there are no more emissions from production and formulation sites. c. Deposition

No quantitative data available

3. Gaps and questions

There is no quantitative data available in the project databank on the emission of endrin due to historical use neither to the atmosphere nor to the aquatic compartment.

VII Measures

1. Measures at production level: a. Contribution to water at production level

Not relevant b. Relevant IPPC sector, documents and available emission criteria

Not relevant c. Voluntary agreements

Not relevant d. Substitution

Not relevant e. Process control, modifications

Not relevant f. Effluent treatment

Not relevant

2. Measures at use level: a. Contribution to water at use level

No data available in project database (on emission due to historical use). b. Use by IPPC sectors

Not relevant c. Use by SME groups

4K0976.01/O0013/JVS/TL 4 Fact sheets on production, use and release of priority substances in the WFD Royal Haskoning Endrin, Final draft For official use only Not relevant d. Use by consumers

Not relevant e. Use in agriculture

Not relevant

3. Measures at community level: a. Sewage treatment

Not relevant b. Waste disposal

No data available in project databank on possible runoff from waste disposal sites. If this occurs endrin may be part of general measures in waste disposal management (like monitoring).

Control and clearance of old stocks. c. Incineration

Not relevant d. Recycling

Not relevant

4. Measures at regulatory level: a. EU level: IPPC emission control

Not relevant b. EU level: Substitution or outphasing

Council Directive of 12 June 1986 on limit values and quality objectives for discharges of certain dangerous substances included in List I of the Annex to Directive 76/464/EEC (86/280/EEC)

Adding endrin to the new Soil Framework Directive. c. EU level: Limitations of use in certain applications

Not relevant d. Other regulatory and/or national policy measures

Endrin is included in various national acts on soil pollution and remediation.

4K0976.01/O0013/JVS/TL 5 Fact sheets on production, use and release of priority substances in the WFD Royal Haskoning Endrin, Final draft For official use only VIII LITERATURE

Brown, K.A., et al, 2000, Exploration of possible future POP control areas, a report produced for European Commission Directorate General Environment, AEA Technology Environment

Esch, G.T. van, E.A.H. Heemstra-Lequin, 1992, International Programme on Chemical Safety (IPCS), Environmental Health Criteria 130, Endrin, World Health Organization

EURECO, 1990, Technical data sheets on substances, candidates for list 1, Directive 76/464/EEC, EURECO

Royal Haskoning, 2002, EaSI-View 10.0, Royal Haskoning

4K0976.01/O0013/JVS/TL 6 Fact sheets on production, use and release of priority substances in the WFD Royal Haskoning Endrin, Final draft For official use only Appendix 1, Scheme of emission routes

A8 A1 Atmospheric Production Traffic deposition Formulation Consumer Historic Agriculture S1 201 Industrial use use Buildings pollution 101 202 IPPC : 101/104/105/106/107 SME : 107.01/111/112 113

SOIL S3.1 Waste

S21 STP GROUNDWATER Runoff S4-S6

Drainage S2

SURFACE WATER

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