Lambda-cyhalothrin (Ref: OMS 3021)

Lambda-cyhalothrin (Ref: OMS 3021)	Last updated: 14/11/2024
(Also known as: PP 321; gamma-cyhalothrin)

SUMMARY

A synthetic pyrethroid insecticide. 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 honeybees. It is moderately toxic to earthworms

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Birds chronic ecotoxicity: High; Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Mammals acute toxicity: High

GENERAL INFORMATION

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

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2026

GB LERAP status

Cat A

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/Spain

Date EC 1107/2009 inclusion expires

31/08/2026

EU Candidate for substitution (CfS)

Yes - low ADI / ARfD / AOEL; two 'Persistent-Bioaccumulative-Toxic' criteria

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓	✓	✓	✓	✓	✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓		✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
✓	✓	✓	✓	✓	✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway
	✓

Additional information

Also used in

Australia, Russia, Morocco

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)

ZXQYGBMAQZUVMI-RDDWSQKMSA-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-/m1/s

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
lambda-cyhalothrin	-

General status

Pesticide type

Insecticide

Substance groups

Pyrethroid insecticide; Pyrethroid ester insecticide

Minimum active substance purity

810 g kg⁻¹

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

Alternative/old CAS RN

76703-65-6

EC number

415-130-7

CIPAC number

463

US EPA chemical code

128897

PubChem CID

6440557

CLP index number

607-252-00-6

Molecular mass

449.85

PIN (Preferred Identification Name)

IUPAC name

[(R)-cyano-(3-phenoxyphenyl)methyl] (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate

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 Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

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

cyhalothrin

gamma-cyhalothrin

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

AgriGuard
Clayton
Syngenta
Bayer
United Cropscience Pte Ltd
NACL Industries Limited

Example products using this active

Dovetail
Hallmark
Seal Z
Warrior
Jackpot 2
Karate 10CS
Molnia
NAMBDA 250CS Insecticide

Formulation and application details

Often supplied as a suspension that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.005

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

500000

Hexane

500000

Toluene

250000

Methanol

250000

Acetone

Melting point (°C)

49.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

275

Flashpoint (°C)

225

Octanol-water partition coefficient at pH 7, 20 °C

3.16 X 10⁰⁵

Calculated

Log P

5.5

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.33

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0002

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

2.00 X 10^-02

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral pH (methanol; 99.0 % w/w): 254nm=1090; 277nm: 2070

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

175

Persistent

DT₅₀ (lab at 20 °C)

175

Persistent

DT₅₀ (field)

26.9

Non-persistent

DT₉₀ (lab at 20 °C)

1193

Very persistent

DT₉₀ (field)

33.4

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 (days) on plant matrix

Value

21.5

Note

Published literature RL₅₀ range 2.26-93.0 days, 3 field & undercover crops, various matrices, n=5

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.3

Note

Published literature RL₅₀ range 0.5-15.3 days, 19 field crops, various matrices, n=31

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Expected to be negligible in field conditions

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 5.2 and pH 6.9, DT₅₀ ~7 days at pH 9

Water-sediment DT₅₀ (days)

15.1

Fast

Water phase only DT₅₀ (days)

0.24

Fast

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

[Wheat grain (dried): 136.8 days @ ~25 DegC, ~80% RH; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

3709

Non-mobile

K_oc (mL g⁻¹)

283707

Notes and range

EU dossier K_d range 1245-6890 mL g⁻¹, K_foc range 70100-200000, Soils=14

Freundlich

K_f (mL g⁻¹)

4167

Non-mobile

K_foc (mL g⁻¹)

290311

¹/_n

0.966

Notes and range

EU dossier K_f range 464-33000 mL g⁻¹, K_foc range 47800-1325000, ¹/_n range 0.85-1.21 mL g⁻¹, Soils=14

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

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

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

12,2

Calculated using the Atkinson method. Assumed 0.5E+06 OH/cm³, 24 hr

Substance of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

4982

(Other literature log BCF range 3.2-3.3 (R3))

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

(RS)-alpha-cyano-3-(4-hydroxyphenoxy)benzyl-(Z)-(1RS)-cis-3-(2-chloro-3, 3, 3-trifluoropropenyl)-2, 2-dimethylcyclopropanecarboxylate

Major fraction

0.121

3-phenoxybenzoic acid

Major fraction

0.314

(Z)-3-(2-chloro-3,3,3-trifluoro-propenyl)-2,2-dimethylcyclo-propane carboxylic acid

Major fraction

0.359

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(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 (Urine; Animal

(1RS)-trans-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethyl-cyclopropane carboxylic acid

Cyhalothrin compound 1b

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.7

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 3950

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5300 mg kg feed⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

3.3

Anas platyrhynchos

High

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 500

Eisenia foetida corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

3.125

Eisenia foetida corr

Moderate

Soil micro-organisms

Nitrogen mineralisation: <-21% effect on ammonification/nitrification
Carbon mineralisation: No significant adverse effect

Dose: 1.25 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

2.73

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.038

Apis mellifera

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.91

Apis mellifera

High

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 0.11

Bombus terrestris

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

=> 0.16

Bombus terrestris

High

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.136

Osmia bicornis

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 0.032

Osmia excavata

High

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as Mortality LR₅₀ g ha⁻¹

4.3

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

0.35

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

0.0017

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00021

Lepomis macrochirus

High

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000031

Pimephales promelas

High

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.0007

Danio rerio

High

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.00023

Daphnia magna

High

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.0000022

Daphnia magna

High

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 0.00015

Ceriodaphnia dubia

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.000003

Americamysis bahia

High

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0015

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.00013

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

0.105

Chironomus riparius

Moderate

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 0.005

Pseudokirchneriella subcapitata

High

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

> 0.31

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀, immobility (mg l⁻¹)

> 0.59

Crassostrea gigas Embryo

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

632

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.066

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.0025

Rat SF=300

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.005

Dog SF=300

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.00063

Rat 1 year SF=300

Dermal penetration studies (%)

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

Occupational

PPE/PPC advised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapid excretion in urine and faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

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

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 6,1
Not explosive or oxidising

CLP classification 2013

Health: H301, H312, H330
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2811

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

lambda-cyhalothrin

French

lambda-cyhalothrine

German

lambda-Cyhalothrin

Danish

lambda-cyhalothrin

Italian

lambda-cialotrina

Spanish

cihalotrin lambda

Greek

Polish

lambda-cyhalotryna

Swedish

lambda-cyhalotrin

Hungarian

lambda-cyhalothrine

Dutch

lambda-cyhalothrin

Norwegian

lambda-cyhalotrin

Record last updated:	14/11/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242