Lambda-cyhalothrin (Ref: OMS 3021)

Lambda-cyhalothrin (Ref: OMS 3021)	Last updated: 01/09/2023
(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

Availability status

Current

Introduction & key dates

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

Examples of species treated

Approval status

GB VMR 2013/2033 approval status

EU Regulatory approval status

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

Veterinary substance type

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.

Molecular targets

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

ATCvet Code

Therapeutic Class

Controlled Drug?

Regulation 37/2010 MRL Classification

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

Physical state

Colourless solid

Related substances & organisms

cyhalothrin

gamma-cyhalothrin

Formulations

Property

Product

Manufacturer

Authorisation Route

UK Legal Class

Example products using this active

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

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)

Refractive Index

Degradation

Property

Value

Source; quality score; and other information

Interpretation

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

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

Manure DT₅₀ (days)

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

3709

Non-mobile

K_oc

283707

Notes and range

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

Freundlich

K_f

4167

Non-mobile

K_foc

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

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

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 (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 28d

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)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00021

Lepomis macrochirus

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000031

Pimephales promelas

High

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

0.00023

Daphnia magna

High

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

0.0000022

Daphnia magna

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

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

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:	01/09/2023
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