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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 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

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 30/06/2016

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

Also used in: Australia

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 -
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
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
  • AgriGuard
  • Clayton
  • Syngenta
  • Bayer
Example products using this active
  • Dovetail
  • Hallmark
  • Seal Z
  • Warrior
  • Jackpot 2
  • Karate 10CS
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 25oC (mPa) 0.0002 A5 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
Foliar DT50 (days) Value 5 A4 -
Note Other data sources: Residue half-life (RL50) = 3.0 days on aubergine fruits (R4)
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
(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 - -
(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) 0.00025 A5 Oncorhynchus mykiss High
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 Moderate
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) - - -
Non-target plants - - -
- - -
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) 0.91 A5 High
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
-
% 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 -
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 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
European MRLs Click here for the EU MRL pesticide database
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

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

: 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 Code is variable depending upon product, often either 3 or 9
Not explosive or oxidising
CLP classification 2013 Health: H301, H312, H330
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: Tuesday 02 February 2016
Contact: aeru@herts.ac.uk