| alpha-cypermethrin (Ref: OMS 3004) |
 |
Environmental Fate - Ecotoxicology - Human Health
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SUMMARY
Alpha-cypermethrin is a widely used pyrethroid insecticide that is approved for use in the EU. It has a low aqueous solubility, in non-volatile and, based on its chemical properties, is not expected to leach to groundwater. However, it is considered to be a serious water pollutant. It is moderately persistent in soil and has been known to persist in water. It is highly toxic to mammals and a recognised irritant. It is relatively non-toxic to birds but is highly toxic to most aquatic organisms and honeybees. It is moderately toxic to earthworms. GENERAL INFORMATION 
for alpha-cypermethrin
Description: An insecticide for control of chewing and sucking insects in a wide range of crops. Also has veterinary treatment applications.
Introduction: 1983, first reported; circa 1985, first introduced
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Belgium |
| Date inclusion expires | 28/02/2015 |
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 |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
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Also registered in: Australia
General status:
| Pesticide type | Insecticide, Veterinary substance | |
| Substance group | Pyrethroid | |
| Substance origin | Synthetic | |
| Mode of action | Non-systemic with contact and stomach action. Sodium channel modulator. | |
| CAS RN | 67375-30-8 | |
| EC number | 257-842-9 | |
| CIPAC number | 454 | |
| US EPA chemical code | - | |
| Chiral molecule | Chiral, a specific isomer or a derivative of a chiral molecule | |
| Chemical formula | C22H19Cl2NO3 | |
| SMILES | Cl/C(Cl)=C/C3C(C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)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 | |
| Molecular mass (g mol-1) | 416.30 | |
| PIN (Preferred Identification Name) | rac-(R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate | |
| IUPAC name | racemate comprising (R)-α-cyano-3-phenoxybenzyl (1S)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate | |
| CAS name | (R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-rel-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate | |
| Other status information | - | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | 3 | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Physical state | Colourless crystals | |
| Related substances & organisms | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active |
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| Example products using this active |
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| UK LERAP status | LERAP Category A | |||
| Formulation and application details | Available in various formulations including crops sprays and livestock pour-ons . | |||
ENVIRONMENTAL FATE
for alpha-cypermethrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.004 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 596000 | A5 - Toluene | - | |
| 21300 | A5 - Methanol | - | ||
| 584000 | A5 - Ethyl acetate | - | ||
| Melting point (oC) | 81.5 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 3.16 X 1005 | Calculated | - |
| Log P | 5.5 | A4 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.33 | A5 | - | |
| Dissociation constant (pKa) at 25oC | 5 | Q3 | - | |
| Note: Weak acid | ||||
| Vapour pressure at 25oC (mPa) | 0.00034 | A5 | Non-volatile | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 6.90 X 10-02 | A5 | Non-volatile | |
| Henry's law constant at 20oC (dimensionless) | 1.75 X 10-05 | Q2 | Moderately volatile | |
GUS leaching potential index  |
-1.18 | 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 | 276nm = 2073, 300nm = 38.64 | A4 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Soil degradation (days) (aerobic) | DT50 (typical) | 35 | A5 | Moderately persistent |
| DT50 (lab at 20oC) | 100 | A5 | Persistent | |
| DT50 (field) | 35 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | 166 | A5 | - | |
| DT90 (field) | 210 | A5 | - | |
| Note | EU dossier Lab studies DT50 range 25-125 days, DT90 range 102-792 days, field studies DT50 range 14-112 day (UK conditions), DT90 range 35-385 days; Other sources:DT50 77 days (DW4) | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | - | A5 | - |
| Note | Very slow degradation by sunlight | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 101 | A5 | Persistent |
| Note | DT50 sensitive to pH: stable at pH 4, 7.3 days at pH 9 | |||
| Water-sediment DT50 (days) | 21 | A5 | Fast | |
| Water phase only DT50 (days) | 1.3 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 577 | A5 | Non-mobile |
| Koc | 57889 | |||
| Notes and range | EU dossier Kd range 821-1042 mL/g | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 91/414 relevancy |
|
| 3-phenoxybenzoic acid |
Soil | 0.480 | Major fraction, Not relevant | |
ECOTOXICOLOGY
for alpha-cypermethrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF | 1204 | A5 | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Bioaccumulation potential | - | Calculated | High | |
| Mammals - Acute oral LD50 (mg kg-1) | 57 | A5 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 5 | A5 Rat | High |
| (ppm diet) | 200 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2025 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.0028 | A5 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.00003 | A5 Pimephales promelas | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.0003 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.00003 | A5 Daphnia magna | - | |
| 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) | - | - | - | |
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.1 | A5 Raphidocelis subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 0.033 | A5 | High |
| Oral acute 48 hour LD50 (μg bee-1) | 0.059 | A5 | High | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 100 | A5 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 | 0.256 | 48 hour, NOER = <0.03 g ha-1 A5 Aphidius rhopalosiphi, adult |
Harmful at 1 kg ha-1 Harmful at 0.1 kg ha-1 Harmful at 0.01 kg ha-1 |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 0.02 | 7 day, NOER = 0.0015 g ha-1 A5 Typhlodromus pyri, protonymph |
Harmful at 1 kg ha-1 Harmful at 0.1 kg ha-1 Harmful at 0.01 kg ha-1 |
| % Effect | 85 | Mortality Dose: 15 g ha-1 L3 Typhlodromus pyri |
Harmful | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.3 kg ha-1, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 0.000015 | A5 Aquatic invertebrates and algae | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for alpha-cypermethrin
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Mammals - Acute oral LD50 (mg kg-1) | 57 | A5 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.593 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.015 | A5 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.04 | A5 Rat, SF=100 | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.01 | A5 Dog, 90 day, SF=100 | - | |
| Dermal penetration studies (%) | 10 | A5 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | Inhalation and dermal routes | |||
| Examples of European MRLs (mg kg-1) | Value | Brassicas, beans (with pods) and peas (with pods): 0.5; Onions, garlic and asparagus: 0.10; Lettuce: 2.0; Cucubits: 0.02; Other vegetables: 0.05; Pomes, plums and cherries: 1.0; Citrus, apricots, nectarines and peaches: 2.0; Canefruit and grapes: 0.5; Barley and oat grains: 0.2; Other cereal grains: 0.05 | ||
| Note | Current May 2007. Limits applies to total of all cypermethrin isomers/enantiomers. For the EU pesticides database click here |
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| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | Respiratory tract irritant | Skin irritant | Eye irritant |
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| General human health issues | Highly toxic by ingestion | |||||||
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
IMDG Transport Code is product specific and usually a 6.1 or 3 | |||
| CLP classification 2013 | - | |||
| EC Risk Classification |
T - Toxic: R25 Xn - Harmful: R48/22 Xi - Irritant: R37 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S2, S36/37/39, S45, S61, S60 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | II | - | Warning - Moderately toxic | |
| UN Number | 3349 for active, variable with product, usually 1993, 3077 or 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for alpha-cypermethrin
| Language | Name |
| English | alpha-cypermethrin |
| French | alphacypermethrine |
| German | alpha-Cypermethrin |
| Danish | alpha-cypermethrin |
| Italian | alfametrina |
| Spanish | alfacipermetrina |
| Greek | - |
| Slovenian | alfa-cipermetrin |
| Polish | alfa-cypermetryna |
| Swedish | alfacypermetrin |
| Hungarian | alphamethrin / alpha cypremethrin |
| Dutch | alfa-cypermethrin |
Record last updated: Saturday 10 January 2015
Contact: aeru@herts.ac.uk