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lambda-cyhalothrin (Ref: OMS 3021)
** PP 321 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

SUMMARY

A synthetic pyrethroid insecticide which is approved for use in the EU. It has a low aqueous solubility, is not 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 pests including aphids, Colarado beetle and thrips

Introduction: 1984, first reported; 1985, introduced Central America and Far East

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Sweden
Date inclusion expires 31/12/2015

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

Also registered in: Australia

General status:
Pesticide type Insecticide
Substance group Pyrethroid
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 -
Chiral molecule No
Chemical formula C23H19ClF3NO3
SMILES Cl\C(=C/[C@H]3[C@@H](C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C)C(F)(F)F
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
Structure diagram/image available? Yes
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 -
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 solid
Related substances & organisms

Formulations:
Property Value
Example manufacturers & suppliers of products using this active
  • AgriGuard
  • Clayton
  • Syngenta
  • Bayer
Example products using this active
  • Dovetail
  • Hallmark
  • Seal Z
  • Warrior
  • Jackpot 2
  • Karate 10CS
UK LERAP status LERAP Category A, LERAP Category B, Broadcast Air Assisted LERAP (depending on situation)
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 25oC (mPa) 0.0002 A5 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 2.00 X 10-02 A5 Non-volatile
Henry's law constant at 20oC (dimensionless) 7.38 X 10-06 K3 Moderately volatile
GUS leaching potential index -3.28 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
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 -
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
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 Very persistent
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 91/414 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
(1RS)-trans-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethyl-cyclopropane carboxylic acid Cyhalothrin compound 1b - - -
(RS)- -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 - -


ECOTOXICOLOGY

for lambda-cyhalothrin

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 4982 A5 (Other literature log BCF range 3.2-3.3 (R3)) Threshold for concern
CT50 (days) Not available -
Bioaccumulation potential - Calculated High
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) 0.00025 A5 Oncorhynchus mykiss -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.00036 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.3 A5 Daphnia magna -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.000003 F3 Americamysis bahia High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 0.00016 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) - - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 0.3 A5 Raphidocelis subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) > 0.31 Q2 Unknown species Moderate
Honeybees Contact acute 48 hour LD50 (μg bee-1) 0.038 A5 High
Oral acute 48 hour LD50 (μg bee-1) - - -
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida corr 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 0.2 7 day
A5 Typhlodromus pyri
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 - - -
% Effect 23 Mortality
Dose: 7.5 g ha-1, 28 day
A5 Pterostichus melanarius
Harmless
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
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 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.0006 A4 Rat, 1 year, SF=300 -
Dermal penetration studies (%) 25 A5 default -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public Slight risk of dietary exposure
Risk assessment indicates that ARfD may be exceeded in a few commodities
Occupational PPE/PPC advised
Examples of European MRLs (mg kg-1) Value Lettuce: 1.0; Eggplants and strawberries: 0.5; Celery: 0.3; Cabbages, beans (with pods), peas (with pods), grapes, nectarines, peaches, lemons, limes and manadarins: 0.2; Broccoli, sweet peppers, tomatoes, summer squash, cauliflowers, cucumbers, grapefruit, currants, gooseberries, pome fruit and other stone fruit: 0.1; Brussel sprouts, melons (not watermelons), winter squash, pumpkins and barley grains: 0.05; Other vegetables, other fruit, beans (edible part), peas (edible part) and other cereal grains: 0.02
Note Current May 2007.
For the EU pesticides database click here
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

General human health issues Harmful if swallowed, inhaled or in contact with skin
Possible immune system and thyroid toxicant in susceptable individuals
Skin sensitiser

: 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 variable depending upon product, often either 3 or 9
Not explosive or oxidising
CLP classification 2013 Danger: H410, H330, H317, H312, H301
Environment: H400, H410
EC Risk Classification T+ - Very toxic: R26
T - Toxic: R25; R43
Xn - Harmful: R21
N - Dangerous for the environment: R50, R53
EC Safety Classification S1/2, S28, S36/37/39, S38, S45, S60, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II - Warning - Moderately toxic
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: Monday 09 June 2014
Contact: aeru@herts.ac.uk