| beta-cyfluthrin (Ref: OMS 3051) |
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SUMMARY
Beta-cyfluthrin is a pyrethroid insecticide approved for use in the EU. It has a low aqueous solubility, semi-volatile and is not expected to leach to groundwater. It is highly toxic to mammals and may be a neurotoxin. It is also highly toxic to fish, aquatic invertebrates and honeybees but slightly less toxic to birds, algae and earthworms. GENERAL INFORMATION 
for beta-cyfluthrin
Description: A pyrethroid insecticide effective against a range of common pests including locusts in a many different crops
Example pests controlled: Migratory locusts; Grasshoppers; Mosquitoes; Bedbugs; Loopers; Cutworms; Spittlebugs; Leaf hoppers; Caterpillars; Armyworms; Weevils; Stinkbugs
Example applications: Alfalfa; Corn; Cotton; Peanuts; Sorghum; Sugarcane; Sugarbeet; Tobacco; Wheat; Brassicas; Sweetcorn; Stone fruit; Root vegetables
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1993, first reported
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Germany/Hungary |
| Date inclusion expires | 31/10/2019 |
| EU Candidate for substitution (CfS) | No |
| 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, USA
Chemical structure:
| Isomerism | An isomeric mixture of the two biologically active diastereoisomeric pairs of cyfluthrin. |
| Chemical formula | C22H18Cl2FNO3 |
| Canonical SMILES | CC1(C(C1C(=O)OC(C#N)C2=CC(=C(C=C2)F)OC3=CC=CC=C3)C=C(Cl)Cl)C |
| Isomeric SMILES | CC1([C@H](C1C=C(Cl)Cl)C(=O)O[C@@H](C#N)C2=CC(=C(C=C2)F)OC3=CC=CC=C3)C |
| International Chemical Identifier key (InChIKey) | OFHFONYRMVKULH-WNYJFNBPSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide | |
| Substance group | Pyrethroid | |
| Minimum active substance purity | 965 g/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 | 1820573-27-0 | |
| EC number | 269-855-7 | |
| CIPAC number | 482 | |
| US EPA chemical code | 118831 | |
| PubChem CID | 56608859 | |
| Molecular mass (g mol-1) | 434.29 | |
| PIN (Preferred Identification Name) | reaction mixture comprising the enantiomeric pair rac-(R)-cyano(4-fluoro-3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in ratio 1:2 with the enantiomeric pair rac-(R)-cyano(4-fluoro-3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate | |
| IUPAC name | (R)-α-cyano-4-fluoro-3-phenoxybenzyl (1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (S)-α-cyano-4-fluoro-3-phenoxybenzyl (1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarbox | |
| CAS name | cyano(4-fluoro-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 freshwater and saltwater aquatic life 0.001 ug/L] | |
| 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 | Helicoverpa armigera Musca domestica Triatoma infestans |
|
| Physical state | Colourless crystals | |
| 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 | Buffer probably required in UK - see product label | |||
| Formulation and application details | Available in a wide variety of formulations including emulsifiable concentrates, granules, oil in water emulsions, suspension concentrates, ULVs and wettable powders. | |||
ENVIRONMENTAL FATE
for beta-cyfluthrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.0012 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 150000 | A4 - Toluene | - | |
| 10000 | A4 - n-Hexane | - | ||
| 200000 | A4 - Dichloromethane | - | ||
| Melting point (oC) | 93.5 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 210 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | L3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 7.94 X 1005 | Calculated | - |
| Log P | 5.9 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.35 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.000056 | A4 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 8.10 X 10-03 | A5 | Non-volatile | |
GUS leaching potential index  |
-1.17 | 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 | No absorption above 290nm | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 13 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 27.8 | A5 | Non-persistent | |
| DT50 (field) | 13 | A5 | Non-persistent | |
| DT90 (lab at 20oC) | 677 | A5 | - | |
| DT90 (field) | 102 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU Dossier Lab studies DT50 range 4-54 days, DT90 range 53-1664 days, field study DT50 range 5-21 days (Germany), DT90 range 70-133 days | |||
| Dissipation rate RL50 on plant matrix | Value | 1.4 | R4 | - |
| Note | Published literature RL50 range 0.8-1.7 days,2 field crops, various matrices, n=3 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 3.9 | R4 | - |
| Note | Published literature RL50 range 3.0-4.7 days, 2 field crops, various matrices, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 1 | A5 | Moderately fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 215 | A5 | Persistent |
| Note | pH sensitive: DT50: 1 year at pH 4, 38 hours at pH 9 | |||
| Water-sediment DT50 (days) | 3 | A5 | Fast | |
| Water phase only DT50 (days) | 1 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 1360 | A4 | Non-mobile |
| Koc | 64300 | |||
| Notes and range | EU dossier Kd range 1116-1764 mL/g, Koc range 73484-180290 mL/g, Soils=5 | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 4-fluoro-3-phenoxybenzoic acid |
Soil | 0.310 | Major fraction, Relevant | |
| 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid |
Soil | 0.100 | Major fraction, Relevant | |
ECOTOXICOLOGY
for beta-cyfluthrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 506 | A5 | Threshold for concern |
| CT50 (days) | 9 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 77 | A5 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 1.5 | L3 Rat | High |
| (ppm diet) | 100 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5000 ppm | A5 Colinus virginianus, as cyfluthrin | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.000068 | A5 Salmonidae | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.00001 | A4 Oncorhynchus mykiss | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.00029 | A4 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.00014 | A5 Daphnia magna | High | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.000002 | F3 Americamysis bahia | High | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | 0.00045 | A5 Chironomus riparius | High | |
| 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) | > 10 | A5 Scenedemus subspicatus | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.01 | A3 Unknown species | Moderate | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.001 | A4 Apis mellifera | High |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.05 | A4 Apis mellifera | High | |
| 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) | 0.46 | R3 Bombus terrestris | High |
| - | ||||
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.12 | R3 Bombus terrestris | High | |
| - | ||||
| Mason bees (Osmia spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.035 | R4 Osmia bicornis | High |
| 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) | > 1000 | A5 Eisenia foetida | Low | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | > 0.133 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 17 | 48 hour A5 Aphidius rhopalosiphi |
- |
| % Effect | 100 | Mortality Dose: 1.675 kg ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | 0.24 | 7 day A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.18 g as/ha |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 0.00005 | A5 Aquatic community | - |
| NOEAEC mg l-1 | 0.00001 | A4 NOEC Aquatic community | - | |
HUMAN HEALTH AND PROTECTION
for beta-cyfluthrin
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) | > 77 | A5 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.081 | A5 Rat (aerosol) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.003 | A5 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.02 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.02 | A5 Rat, 90 day, SF=100 | - | |
| Dermal penetration studies (%) | 10 | A5 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| 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 | |||
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A0; B0; C0; D0; E0 |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | No further information available | |||||||
| 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 |
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| General |
No information available IMDG Transport Code is usually 6.1 |
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| CLP classification 2013 | Health: H300, H330 Environment: H400, H410 |
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| EC Risk Classification |
T+ - Very toxic: R26/28 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S1/2, S36/37/39, S45, S60, S61 | |||
| WHO Classification | Ib | - | Highly hazardous | |
| UN Number | Usually 2588 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for beta-cyfluthrin
| Language | Name |
| English | beta-cyfluthrin |
| French | betacyflutrine |
| German | beta-Cyfluthrin |
| Danish | betacyfluthrin |
| Italian | beta-ciflutrina |
| Spanish | beta-ciflutrina |
| Greek | beta-cyfluthrin |
| Slovenian | beta-ciflutrin |
| Polish | beta-cyflutryna |
| Swedish | betacyflutrin |
| Hungarian | beta-ciflutrin |
| Dutch | - |
Record last updated: Thursday 20 June 2019
Contact: aeru@herts.ac.uk