| mirex (Ref: GC 1283) |
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SUMMARY
Mirex is an obsolete organochlorine insecticide. Toxic to humans and know to be a carcinogen. Mirex is also a reproduction and CNS toxin. It is practically insoluble and takes several years to degrade in soil. It is not expected to leach into groundwater but will accumulate in sediements. Environmentally persistent and will bioaccumulate. Moderately toxic to wildlife. GENERAL INFORMATION 
for mirex
Description: Now banned, Mirex was used to control ants and had several other non pesticide uses
Example pests controlled: Fire ants; Harvester ants
Example applications: Agricultural fields; Non-cropped areas
Efficacy & activity: -
Availability status: Obsolete, Discontinued, banned
Introduction & key dates: 1946, first reported
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Not applicable |
| 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: 
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 |
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Chemical structure:
| Isomerism | - |
| Chemical formula | C10Cl12 |
| Canonical SMILES | C12(C3(C4(C5(C3(C(C1(C5(C2(C4(Cl)Cl)Cl)Cl)Cl)(Cl)Cl)Cl)Cl)Cl)Cl)Cl |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | GVYLCNUFSHDAAW-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C10Cl12/c11-1-2(12)7(17)4(14)3(13,5(1,15)9(7,19)20)6(1,16)10(21,22)8(2,4)18 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide | |||
| Substance group | Organochlorine | |||
| Minimum active substance purity | - | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Central nervous system stimulant with contact activity, ingested toxin. | |||
| CAS RN | 2385-85-5 | |||
| EC number | 219-196-6 | |||
| CIPAC number | 375 | |||
| US EPA chemical code | 039201 | |||
| PubChem CID | 16945 | |||
| Molecular mass (g mol-1) | 545.54 | |||
| PIN (Preferred Identification Name) | 1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachloro-1,1a,3,3a,4,5,5a,5b-octahydro-1H-1,3,4-(epimethanetriyl)cyclobuta[cd]pentalene | |||
| IUPAC name | dodecachloropentacyclodecane | |||
| CAS name | 1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachlorooctahydro-1,3,4-metheno-1H-cyclobuta[cd]pentalene | |||
| Other status information | POP; LRTAP Annex I; OSPAR soc; Marine Pollutant; Banned 1978 | |||
| Relevant Environmental Water Quality Standards | - | |||
| 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 | - | |||
| Physical state | White crystalline solid | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | - | |||
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.0001 | F3 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 17000 | Q2 - Chloroform | - | |
| 14300 | Q2 - Xylene | - | ||
| Melting point (oC) | 485 | F3 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.91 X 1005 | Calculated | - |
| Log P | 5.28 | F3 | High | |
| Bulk density (g ml-1)/Specific gravity | - | - | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | - | - | - | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 839.4 | F3 | Volatile | |
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 | 1.16 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 300 | F3 | Persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Environmentally stable, DT50 circa 3000+ days, some reports say up to 10 years (R3) | |||
| 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 | Stable | Q3 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | Q3 | - |
| Note | - | |||
| Water-sediment DT50 (days) | Stable | Q3 | - | |
| Water phase only DT50 (days) | Stable | Q3 | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | F3 | Non-mobile |
| Koc | 5794 | |||
| Notes and range | Log10 Koc 3.763 | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| chlordecone (Ref: ENT 16391) | Soil | - | Not assessed under 91/414 or 1107/2009 | |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 51400 | F3 | High potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 235 | V3 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2400 | V3 Anas platyrhynchos | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 100 | F4 Oncorhynchus mykiss | Low | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 0.1 | F4 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) | 0.1 | F4 Chlorella pyrenoidosa | 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) | - | - | - |
| 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) | 7.15 | CA3 | 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) | - | - | - | |
| 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 | - | - | - | |
| 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 mirex
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | > 235 | V3 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | V3 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | - | - | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | - | - | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | - | - | - | |
| 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 I | - | - | |
| Exposure Routes | Public | Main concerns were from food residues but substance is now obsolete and banned in most countries so risk now minimal | ||
| 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 | |||
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A0; B0; C0; D0; E0 |
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- |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Moderately toxic Liver, thyroid and kidney toxicant Endocrine issues - Weak estrogen effect |
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| 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 |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
No information available | |||
| CLP classification 2013 | - | |||
| EC Risk Classification |
Carcinogen category 3: R40 Reproduction risk category 3: R62, R63, R64 Xn - Harmful: R22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S13, S36/37, S46, S60, S61 | |||
| WHO Classification | O | - | Obsolete substance | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | mirex |
| French | - |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | - |
| Greek | - |
| Slovenian | - |
| Polish | - |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Thursday 31 May 2018
Contact: aeru@herts.ac.uk