Gamma-cyhalothrin (Ref: DE 225)

Gamma-cyhalothrin (Ref: DE 225)	Last updated: 28/08/2024
(Also known as: XDE 225)

SUMMARY

Gamma-cyhalothrin is a broad-spectrum pyrethroid insecticide. It has a low aqueous solubility, volatile and, based on its chemical properties, would not be expected to leach to groundwater. It is non-persistent in soil systems and would not normally persist in aqueous systems. It has a high mammalian toxicity and there is some concern regarding its potential to bioaccumulate. It is considered to be a neurotoxicant. It is highly toxic to honeybees and many aquatic organisms and moderately toxic to birds and 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: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High; Bees acute contact ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

A pyrethroid insecticide offering broad-spectrum control of insect pests in a wide range of agricultural crops

Example pests controlled

Sucking and chewing insect pests

Example applications

Corn; Oilseed rape; Cereals

Efficacy & activity

Availability status

Current

Introduction & key dates

late-1990s, registered Europe; 2003, registered Indonesia

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2025

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

31/03/2025

EU Candidate for substitution (CfS)

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, Argentina, Chile, China, Indonesia, South Africa, Mexico, Romania, USA, Morocco

Chemical structure

Isomerism

Cyhalothrin is a molecule with 3 chiral centres. Gamma-cyhalothrin is considered to be the most insecticidally active isomer.

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-GCMPRSNUSA-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

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
gamma-cyhalothrin	-

General status

Pesticide type

Insecticide

Substance groups

Pyrethroid insecticide; Pyrethroid ester insecticide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier: none declared

Substance origin

Synthetic

Mode of action

Non-systemic acting by contact and/or ingestion. Sodium channel modulator, distrupts nerve function

CAS RN

76703-62-3

EC number

435-840-0

CIPAC number

768

US EPA chemical code

12887

PubChem CID

6440554

CLP index number

No data found

Molecular mass

449.85

PIN (Preferred Identification Name)

IUPAC name

(S)-α-cyano-3-phenoxybenzyl (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate

CAS name

(S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylate

Other status information

Marine pollutant; PAN Listed as Highly Hazardous Chemical

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

Helicoverpa armigera

Physical state

Off-white coloured solid

Related substances & organisms

cyhalothrin

lambda-cyhalothrin

Formulations

Property

Value

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

Cheminova
Dow AgroSciences

Example products using this active

Fighter
Trojan
Bull
Vantex
Proaxis
Fentrol
Corello GF-317
Declare

Formulation and application details

Typically formulated as suspension in a solvent

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0021

Low

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

500000

Acetone

500000

Ethyl acetate

138000

Methanol

30700

Heptane

Melting point (°C)

55.6

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

245

Flashpoint (°C)

398

(auto-ignition)

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

9.12 X 10⁰⁴

Calculated

Log P

4.96

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.32

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

3.45 X 10^-04

Low volatility

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

0.0221

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

8.2

24 hr

Volatilisation is not considered critical for air pollution

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

Acidic soln.: 204nm=45600
Neutral soln.: 204nm=45700
Basic soln.: 219nm=29600

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

26.8

Non-persistent

DT₅₀ (lab at 20 °C)

26.8

Non-persistent

DT₅₀ (field)

26.5

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 16.6-33.8 days; Manufacturers published literature lab studies DT₅₀ 28-51 days, Field studies DT₅₀ range 18-30 days, DT₉₀ range 58-94 days; There are a few other literature references available but indications are that DT₅₀ is a few weeks.

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

136

Persistent

Note

pH sensitive: stable at pH 5, 1.1 days at pH 9

Water-sediment DT₅₀ (days)

34.5

Moderately fast

Water phase only DT₅₀ (days)

6.4

Moderately fast

Sediment phase only DT₅₀ (days)

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

622

Non-mobile

K_oc (mL g⁻¹)

59677

Notes and range

EU dossier K_d range 239-826 mL g⁻¹, K_oc range 34133-92692 mL g⁻¹, soils=4

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.10

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

4.08

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

2240

Whole fish

Threshold for concern

CT₅₀ (days)

9.1

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

Minor fraction

3-phenoxybenzoic acid

Minor fraction

3-(4-hydroxyphenoxy)benzaldehyde

Major fraction

0.122

Transient

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

3-(4-hydroxyphenoxy)benzaldehyde

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2-hydroxy-methyl-2-methyl-cyclopropane carboxylic acid

Cyhalothrin compound XI

Animal

3-(4'-hydroxy)-phenoxy-benzoic acid

Cyhalothrin compound XXIII

Rat (Urine); Animal

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

Cyhalothrin compound 1a

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

Cyhalothrin compound 1b

(RS)-á -cyano-3-phenoxy-benzyl alcohol

Cyhalothrin compound III

3-phenoxybenzaldehyde

Cyhalothrin compound IV

(RS)-3-phenoxymandelamide

Cyhalothrin compound IX

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)

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

> 650

Eisenia foetida corr

Moderate

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

0.25

Eisenia foetida 56 day corr

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 375g kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

0.005

Apis mellifera

High

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

4.2

Apis mellifera

Moderate

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

Chronic

Notes

[The residual time to 25% mortality (RT25) value for honeybees is 24 hrs - USEPA data]

Bumblebees (Bombus spp.)

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

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

Mason bees (Osmia spp.)

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

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)

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

0.23

Aphidius rhopalosiphi Adult

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

0.0006

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)

0.000035

Lepomis macrochirus

High

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

0.000038

Pimephales promelas

High

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

> 0.002

Danio rerio

High

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

0.000045

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)

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

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

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

0.000047

Chironomus riparius

High

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

0.000126

Chironomus riparius

High

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

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

2.85

Pseudokirchneriella subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

1643

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.028

Rat

Other Mammal toxicity endpoints

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

0.0012

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

0.0025

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

Not applicable

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

0.0003

Dermal penetration studies (%)

2-32%

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses with PPE/PPC

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, 90% in 48 hours

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Harmful by inhalation
Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9

CLP classification 2013

Health: H301, H312
Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

gamma-cyhalothrin

French

Gamma-cyhalothrine

German

gamma-Cyhalothrin

Danish

gamma-cyhalothrin

Italian

gamma-cialotrina

Spanish

gamma-cihaltrina

Greek

Polish

gamma-cyhalotryna

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	28/08/2024
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