Gamma-cyhalothrin (Ref: DE 225)

Gamma-cyhalothrin (Ref: DE 225)	Last updated: 06/11/2019
(Also known as: XDE 225)

SUMMARY

Gamma-cyhalothrin is a broad-spectrum pyrethroid insecticide approvd for use in EU. 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 honey bees and many aquatic organisms and moderately toxic to birds and earthworms.

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, Europe; 2003, Indonesia

UK regulatory status

UK approval status

Not approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Approved

Dossier rapporteur/co-rapporteur

Date inclusion expires

31/03/2025

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) or known to be used (#) in the following EU-27 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
					✓			✓

Also used in

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

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

General status

Pesticide type

Insecticide

Substance group

Pyrethroid

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

CIPAC number

768

US EPA chemical code

12887

PubChem CID

6440554

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Helicoverpa armigera

Physical state

Off-white coloured solid

Formulations

Property

Value

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

Fighter
Trojan
Bull
Vantex
Proaxis
Fentrol
Corello GF-317

Example products using this active

Cheminova
Dow AgroSciences

UK LERAP status

No UK approval for use as a pesticide under EC Regulation 1107/2009

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

Bulk density (g ml⁻¹)

1.32

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C

3.45 X 10^-04

Low volatility

Henry's law constant at 25 °C

0.0221

Non-volatile

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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

Minor fraction

3-phenoxybenzoic acid

Soil

Minor fraction

3-(4-hydroxyphenoxy)benzaldehyde

Soil

0.122

Major fraction, 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 (Urinary); 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

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

2240

(whole fish)

Threshold for concern

CT₅₀ (days)

9.1

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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)

Non-target plants

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

2.85

Pseudokirchneriella subcapitata

Moderate

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

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)

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 pollinators (1)

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

Mode of exposure

Other pollinators (2)

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

Mode of exposure

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

0.23

Mortality
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.0006

Mortality
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 375g kg⁻¹ soil

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

Rat SF=400 as cyhalothrin

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

0.0025

Dog SF=200 as lambda cyhalothrin

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

Rat SF=1600 as cyhalothrin

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

CLP classification 2013

Health: H301, H312
Environment: H400, H410

EC Risk Classification

T+ - Very toxic: R26
T - Toxic: R25
Xn - Harmful: R21, R43, R48
N - Dangerous for the environment: R50/53

EC Safety Classification

S24, S37, S60

WHO Classification

NL (Not listed)

UN Number

3082

Waste disposal & packaging

Packging Group III (minor danager)

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

Record last updated:	06/11/2019
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