Gamma-cyhalothrin (Ref: DE 225)

Gamma-cyhalothrin (Ref: DE 225)	Last updated: 29/06/2023
(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

Availability status

Current

Introduction & key dates

Late 1990s, Europe; 2003, Indonesia

Examples of species treated

Approval status

GB VMR 2013/2033 approval status

EU Regulatory approval status

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

Veterinary substance type

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

Molecular targets

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

ATCvet Code

Therapeutic Class

Controlled Drug?

Regulation 37/2010 MRL Classification

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

Physical state

Off-white coloured solid

Related substances & organisms

cyhalothrin

lambda-cyhalothrin

Formulations

Property

Product

Manufacturer

Authorisation Route

UK Legal Class

Example products using this active

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

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)

Refractive Index

Degradation

Property

Value

Source; quality score; and other information

Interpretation

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)

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.

Manure DT₅₀ (days)

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

622

Non-mobile

K_oc

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

K_foc

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

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

Metabolising enzymes

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 days 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

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.000035

Lepomis macrochirus

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000038

Pimephales promelas

High

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

0.000045

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)

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

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)

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

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 danager)

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:	29/06/2023
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