| lambda-cyhalothrin (Ref: OMS 3021) |
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SUMMARY
A synthetic pyrethroid insecticide which is approved for use in the EU. It has a low aqueous solubility, is relatively volatile, is non mobile and, based on chemical properties, there is a low risk of it leaching to ground water. Lambda cyhalothrin is highly toxic to mammals and is a known irritant. It is also highly toxic to fish, aquatic invertebrates and honey bees. It is moderately toxic to earthworms GENERAL INFORMATION 
for lambda-cyhalothrin
Description: A quick-acting insecticide used to control a wide spectrum of agricultural crop and public health pests
Example pests controlled: Aphids; Thrips; Colorado beetles; Caterpillars; Mosquitoes; Ticks; Flies
Example applications: Cotton; Cereals; Potatoes; Hops; Vegetables
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1984, first reported; 1985, introduced Central America and Far East
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Sweden/Spain |
| Date inclusion expires | 31/03/2023 |
| EU Candidate for substitution (CfS) | Yes - low ADI / ARfD / AOEL; two 'Persistent-Bioaccumulative-Toxic' criteria |
| 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 |
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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; Russia
Chemical structure:
| Isomerism | Lambda-cyhalothrin consists of one enantiomeric pair of isomers and is the more biologically active form of cyhalothrin |
| Chemical formula | C23H19ClF3NO3 |
| Canonical SMILES | CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(C(F)(F)F)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(/C(F)(F)F)\Cl)C |
| International Chemical Identifier key (InChIKey) | BFPGVJIMBRLFIR-GUCBCRIZSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/b19-12-/t17-,18?,20-/m0/s1 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide | |
| Substance group | Pyrethroid | |
| Minimum active substance purity | 810 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Synthetic | |
| Mode of action | Non-systemic, contact and stomach action. Some repellant properties. Sodium channel modulator. | |
| CAS RN | 91465-08-6 | |
| EC number | 415-130-7 | |
| CIPAC number | 463 | |
| US EPA chemical code | 128897 | |
| PubChem CID | 71464055 | |
| Molecular mass (g mol-1) | 449.85 | |
| PIN (Preferred Identification Name) | - | |
| IUPAC name | (R)-a-cyano-3-phenoxybenzyl (1S)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate and (S)-a-cyano-3-phenoxybenzyl (1R)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate | |
| CAS name | (R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-rel-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | - | |
| 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 | Aedes aegypti Aphis gossypii Cydia pomonella Meligethes aeneus Thrips tabaci many others |
|
| Physical state | Colourless 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 | Buffer probably required in UK - see product label | |||
| Formulation and application details | Often supplied as a suspension that is mixed with water and used as a spray. | |||
ENVIRONMENTAL FATE
for lambda-cyhalothrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.005 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 500000 | A5 - Hexane | - | |
| 500000 | A5 - Toluene | - | ||
| 250000 | A5 - Methanol | - | ||
| 250000 | A5 - Acetone | - | ||
| Melting point (oC) | 49.2 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 275 | A5 | - | |
| Flashpoint (oC) | 225 | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 3.16 X 1005 | Calculated | - |
| Log P | 5.5 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.33 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.0002 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.00 X 10-02 | A5 | Non-volatile | |
GUS leaching potential index  |
-2.09 | 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 | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral pH (methanol; 99.0 % w/w): 254nm=1090; 277nm: 2070 | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 175 | A5 | Persistent |
| DT50 (lab at 20oC) | 175 | A5 | Persistent | |
| DT50 (field) | 26.9 | A5 | Non-persistent | |
| DT90 (lab at 20oC) | 1193 | A5 | - | |
| DT90 (field) | 33.4 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier Lab studies DT50 range 43-1000 days, DT90 range 82 - >5000 days; Field study DT50 range 10.1-47.5 days (Germany), DT90 range 33.6-158 days | |||
| Dissipation rate RL50 on plant matrix | Value | 2.6 | R4 | - |
| Note | Published literature RL50 range 3.1-93.0 days, 3 field & undercover crops, various matrices, n=4 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 4.9 | R4 | - |
| Note | Published literature RL50 range 0.5-15.3 days, 18 field crops, various matrices, n=28 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 40 | A3 | Stable |
| Note | Expected to be negligible in field conditions | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable pH 5.2 and pH 6.9, DT50 ~7 days at pH 9 | |||
| Water-sediment DT50 (days) | 15.1 | A5 | Fast | |
| Water phase only DT50 (days) | 0.24 | A5 | Fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 3709 | A5 | Non-mobile |
| Koc | 283707 | |||
| Notes and range | EU dossier Kd range 1245-6890 mL/g, Kfoc range 70100-200000, Soils=14 | |||
| Freundlich | Kf | 4167 | A4 | Non-mobile |
| Kfoc | 290311 | |||
| 1/n | 0.966 | |||
| Notes and range | EU dossier Kf range 464-33000 mL/g, Kfoc range 47800-1325000, 1/n range 0.85-1.21 mL/g, Soils=14 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| (RS)-alpha-cyano-3-(4-hydroxyphenoxy)benzyl-(Z)-(1RS)-cis-3-(2-chloro-3, 3, 3-trifluoropropenyl)-2, 2-dimethylcyclopropanecarboxylate |
Soil | 0.121 | Major fraction, Relevancy unknown | |
| 3-phenoxybenzoic acid |
Soil | 0.314 | Major fraction, Relevant | |
| (Z)-3-(2-chloro-3,3,3-trifluoro-propenyl)-2,2-dimethylcyclo-propane carboxylic acid |
Soil | 0.359 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| (RS)-á -cyano-3-phenoxy-benzyl alcohol | Cyhalothrin compound III | - | - | - |
| 3-phenoxybenzaldehyde | Cyhalothrin compound IV | - | - | - |
| (RS)-3-phenoxymandelamide | Cyhalothrin compound IX | - | - | - |
| 3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2-hydroxy-methyl-2-methyl-cyclolambda-propane carboxylic acid | Cyhalothrin compound XI | Animal | - | - |
| 3-(4'-hydroxy)-phenoxy-benzoic acid | Cyhalothrin compound XXIII | Rat (Urinary; Animal | - | - |
| (1RS)-trans-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethyl-cyclopropane carboxylic acid | Cyhalothrin compound 1b | - | - | - |
ECOTOXICOLOGY
for lambda-cyhalothrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 4982 | A5 (Other literature log BCF range 3.2-3.3 (R3)) | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 56 | A5 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 0.7 | A5 Rat | High |
| (ppm diet) | 10 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 3950 | A5 Anas platyrhynchos | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5300 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.00021 | A5 Lepomis macrochirus | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.000031 | A5 Pimephales promelas | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.00023 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.0000022 | A5 Daphnia magna | High | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.000003 | A5 Americamysis bahia | High | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | 0.0015 | A5 Chironomus riparius | High | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.00013 | A5 Chironomus riparius | High | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | 0.105 | A5 Chironomus riparius | Moderate | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 0.005 | A5 Pseudokirchneriella subcapitata | High | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | > 0.31 | Q2 Unknown species | Moderate | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.038 | A5 Apis mellifera | High |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.91 | A5 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) | > 0.11 | R4 Bombus terrestris | High |
| - | ||||
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | => 0.16 | R4 Bombus terrestris | High | |
| - | ||||
| Mason bees (Osmia spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.136 | 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) | > 500 | A5 Eisenia foetida corr | Moderate | |
| Earthworms - Chronic NOEC, reproduction (mg kg-1) | 3.125 | A5 Eisenia foetida corr | Moderate | |
| Other soil macro-organisms | Acute LC50 (mg kg-1) | - | - | - | Chronic NOEC (mg kg-1) | 2.73 | A5 Folsomia candida, 28d | - |
| Other arthropod (1) | LR50 g ha-1 | 0.2 | 7 day A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 23 | Mortality Dose: 7.5 g ha-1, 28 day A5 Pterostichus melanarius |
- | |
| Soil micro-organisms | Nitrogen mineralisation: <-21% effect on ammonification/nitrification Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.25 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for lambda-cyhalothrin
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) | 56 | A5 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 632 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.066 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.0025 | A5 Rat, SF=300 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.005 | 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) | 0.00063 | A4 Rat, 1 year, SF=300 | - | |
| Dermal penetration studies (%) | 25 | A5 default | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Routes | Public | Slight risk of dietary exposure Risk assessment indicates that ARfD may be exceeded in a few commodities |
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| Occupational | PPE/PPC advised | |||
| 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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A3; B2; C3; D0; E3 |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Harmful if swallowed, inhaled or in contact with skin Possible immune system and thyroid toxicant in susceptable individuals |
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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 |
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| General |
IMDG Transport Code is variable depending upon product, often either 3 or 9 Not explosive or oxidising |
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| CLP classification 2013 | Health: H301, H312, H330 Environment: H400, H410 |
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| EC Risk Classification |
T+ - Very toxic: R26 T - Toxic: R25; R43 Xn - Harmful: R21 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S1/2, S28, S36/37/39, S38, S45, S60, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| UN Number | 3349 for active, variable with product, usually 1993 or 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for lambda-cyhalothrin
| Language | Name |
| English | lambda-cyhalothrin |
| French | lambda-cyhalothrine |
| German | lambda-Cyhalothrin |
| Danish | lambda-cyhalothrin |
| Italian | lambda-cialotrina |
| Spanish | cihalotrin lambda |
| Greek | - |
| Slovenian | lambda-cihalotrin |
| Polish | lambda-cyhalotryna |
| Swedish | lambda-cyhalotrin |
| Hungarian | lambda-cyhalothrine |
| Dutch | lambda-cyhalothrin |
Record last updated: Tuesday 10 December 2019
Contact: aeru@herts.ac.uk