| beta-cypermethrin (Ref: OMS 3068) |
 |
Environmental Fate - Ecotoxicology - Human Health
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SUMMARY
A pyrethroid insecticide currently within the EU regulatory review process. It has a low aqueous solubility, in relatively volatile and, based on its chemical properties, is not expected to leach to groundwater. It is non-persistent in soil systems. It is highly toxic to mammals and there is some concern regarding its ability to bioconcentrate. It is moderately toxic to birds, earthworms and highly toxic to honey bees and most aquatic species except for algae where there is a reduced risk. GENERAL INFORMATION 
for beta-cypermethrin
Description: A broad spectrum insecticide used to control common pests in crops, public health and veterinary situations.
Example pests controlled: Aphids; Cockroaches; Fleas; Ticks; Flies; Mosquitoes
Example applications: Oilseed rape; Wheat; Barley; Maize; Livestock; Public health situations
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1989
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | United Kingdom |
| 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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Also used in: Australia
Chemical structure:
| Isomerism | Cypermethrin is a chiral molecule and consists of eight isomers, four cis and four trans. Beta -cypermethirn is a reaction mixture of two enantiomeric forms. |
| Chemical formula | C22H19Cl2NO3 |
| Canonical SMILES | CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C |
| Isomeric SMILES | CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C |
| International Chemical Identifier key (InChIKey) | GUQZCTLEJXHSIH-RZAVTOELSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1 |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide, Veterinary substance | |
| Substance group | Pyrethroid | |
| Minimum active substance purity | >960mg/kg | |
| Known relevant impurities | EU dossier: none declared | |
| Substance origin | Synthetic | |
| Mode of action | Non-systemic with contact and stomach action. Sodium channel modulator. | |
| CAS RN | 65731-84-2 | |
| EC number | 265-898-0 | |
| CIPAC number | 632 | |
| US EPA chemical code | 109702 | |
| PubChem CID | 6455379 | |
| Molecular mass (g mol-1) | 416.3 | |
| PIN (Preferred Identification Name) | reaction mixture comprising the enantiomeric pair rac-(R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in ratio approximately 2:3 with the enantiomeric pair rac-(R)-cyano(3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate | |
| IUPAC name | (R)-α-cyano-3-phenoxybenzyl (1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (S)-α-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate | |
| CAS name | cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | UK Environment Agency non-statutory standard for the protection of aquatic life in freshwater and saltwater annual average 0.0002 ug/L, max acceptable conc 0.002 ug/L UK statutory standard for water quality: ‘Good’ for fresh, transitional & saltwater: 0.1 ng/L as annual mean conc, 0.4 ng/L 95th percentile |
|
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | 3 | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | Musca domestica Triatoma infestans |
|
| Physical state | White powder | |
| 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 | Usually supplied as an emulsifiable concentrate. | |||
ENVIRONMENTAL FATE
for beta-cypermethrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.9 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 14000 | A5 - n-Heptane | - | |
| 45000 | A5 - Methanol | - | ||
| 26000 | A5 - Octanol | - | ||
| 1000000 | A5 - Ethyl acetate | - | ||
| Melting point (oC) | 63 | A5 | - | |
| Boiling point (oC) | 253 | A5 - Decomposes | - | |
| Degradation point (oC) | 253 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.31 X 1005 | Calculated | - |
| Log P | 5.8 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.34 | L3 | - | |
| Dissociation constant (pKa) at 25oC | n/d | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.02 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 9.1 X 10-08 | A5 | Non-volatile | |
GUS leaching potential index  |
-1.52 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 5.35 X 10-03 | Calculated | - |
| Note | Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | Acidic: 204nm=44881, 277nm=714 Neutral: 203nm-61241 Basic: 208nm=39764, 310nm=2756 |
A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 27.1 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 27.1 | A5 | Non-persistent | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier DT50 lab studies range 15.2-43.4 days days ; DT90 range 257-734 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 4.9 | R4 | - |
| Note | Published literature RL50 range 3.7-6.0 days, 2 field crops, various matrices, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | - | - | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | - | - | - |
| Note | - | |||
| Water-sediment DT50 (days) | 22.2 | A5 | Fast | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 1369 | A5 | Non-mobile |
| Kfoc | 114676 | |||
| 1/n | 1.001 | |||
| Notes and range | EU dossier Kf range 889-1622 mL/g, Kfoc range 41167-249607 mL/g, 1/n range 0.946-1.072, Soils=4 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 3-phenoxybenzoic acid |
Soil | 0.171 | Major fraction; Relevant | |
| 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate |
Soil | 0.271 | Major fraction; Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 3-phenoxybenzaldehyde | - | Aqueous and soil photolysis | - | - |
| 3-phenoxybenzylactetic acid | - | Aqueous photolysis | - | - |
| Phenol | - | Aqueous photolysis | - | - |
| Cyperamide | - | Aqueous and soil photolysis; Hydrolysis | - | - |
| alpha-carbamoyl-3-phenoxybenzyl-alcohol | - | Soil photolysis | - | - |
| 2-OH-PBAcid | - | - | - | - |
| PBAlcohol | - | - | - | - |
| N-(3-phenoxybenzoyl)glycerine | - | - | - | - |
| N-(3-phenoxybenzoyl)glutamic acid | - | - | - | - |
| 3-(4-hydroxyphenoxy)benzoic acid O-sulfate | - | - | - | - |
| taurine-PBA | - | Mouse | - | - |
ECOTOXICOLOGY
for beta-cypermethrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 846 | A5 | Threshold for concern |
| CT50 (days) | 2.0 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 93.0 | A5 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L3 Rat | - |
| (ppm diet) | > 250 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Collinus virginians | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.00039 | A5 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.00037 | A5 Pimephales promelas, 34 days | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.00042 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.0000059 | A5 Mysidopsis bahia | High | |
| 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) | 0.00006 | A5 Chironomus riparius | High | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 0.053 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 0.014 | A5 | High |
| Oral acute 48 hour LD50 (μg bee-1) | 0.05 | A5 | High | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 150 | A5 Eisenia foetida, corr | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 0.243 | A5 Eisenia foetida, corr | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 100 | Mortality, Dose 12.5g ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 100 | Mortality, Dose 12.5g ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.67mg kg-1, 28days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for beta-cypermethrin
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) | 93.0 | A5 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 1.06 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.0016 | A5 Dog, SF=300 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.0016 | A5 Dog, SF=300 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.0008 | A5 Dog, SF=600 | - | |
| Dermal penetration studies (%) | 5-7 | A5 Concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Risk from vapour exposure risk identified for bystanders in the vicinity | ||
| Occupational | PPE/PPC required to reduce exposure risk | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Risk of serious damage to the eye | |||||||
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
IMDG Transport class 6.1 Not explosive or oxidising |
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| CLP classification 2013 | Health: H301, H318, H332, H335 Environment: H410 |
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| EC Risk Classification |
T - Toxic: R25 Xn - Harmful: R20, R41 Xi - Irritant: R37 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S22, S26, S39, S60, S61 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | - | - | ||
| UN Number | - | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for beta-cypermethrin
| Language | Name |
| English | beta-cypermethrin |
| French | betacypermethrine |
| German | beta-Cypermethrin |
| Danish | betacypermethrin |
| Italian | beta-cipermetrina |
| Spanish | beta-cipermetrina |
| Greek | - |
| Slovenian | beta-cipermetrin |
| Polish | beta-cypermetryna |
| Swedish | - |
| Hungarian | beta-cypermethrin |
| Dutch | - |
Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk