Zeta-cypermethrin (Ref: FMC 56701)

Zeta-cypermethrin (Ref: FMC 56701)	Last updated: 31/07/2024
(Also known as: zetacypermethrin; z-cypermethrin ; F 56701)

GENERAL INFORMATION

Description

An insecticide used to control beetles, aphids and Lepidoptera in a range of crops

Availability status

Current

Introduction & key dates

1984, introduced

Examples of veterinary uses

Examples of species treated

Approval status

VMR 2013/2033 approval status (GB/UK)

EU Regulatory approval status

Chemical structure

Isomerism

Cypermethrin is a chiral molecule and consists of eight isomers, four cis and four trans. Zeta-cypermethrin is a mixture of stereoisomer pairs

Chemical formula

C₂₂H₁₉Cl₂NO₃

Canonical SMILES

CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

Isomeric SMILES

CC1(C(C1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

International Chemical Identifier key (InChIKey)

KAATUXNTWXVJKI-QPIRBTGLSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
zeta-cypermethrin	-

General status

Veterinary substance type

Substance groups

Pyrethroid insecticide; Pyrethroid ester insecticide

Minimum active substance purity

850 g kg⁻¹

Known relevant impurities

EU dossier - toluene <2g kg⁻¹, tars 12.5 g kg⁻¹

Substance origin

Synthetic

Mode of action

Contact and stomach action. Acts mainly on the nervous system. Sodium channel modulator.

Molecular targets

CAS RN

97955-44-7

EC number

257-842-9

CIPAC number

733

US EPA chemical code

109702/129064

PubChem CID

12617362

CLP index number

No data found

Therapeutic Class

ATCvet Code

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

416.31

PIN (Preferred Identification Name)

mixture of the stereoisomer pairs (S)-cyano(3-phenoxyphenyl)methyl (1R*,3R*)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate and (S)-cyano(3-phenoxyphenyl)methyl (1R*,3S*)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in the ratio range 45–55 to 55–45 respectively

IUPAC name

mix of (S)-α-cyano-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

CAS name

(S)-cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Other status information

Relevant Environmental Water Quality Standards

UK Environment Agency non-statutory standard for the protection of aquatic life in freshwater and saltwater annual average 0.0002 µg l⁻¹, max acceptable conc 0.002 µg l⁻¹
UK statutory standard for water quality: ‘Good’ for fresh, transitional & saltwater: 0.1 ng l⁻¹ as annual mean conc, 0.4 ng l⁻¹ 95th percentile

Physical state

Pale yellow viscous liquid

Related substances & organisms

cypermethrin

alpha-cypermethrin

beta-cypermethrin

theta-cypermethrin

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.039

Low

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

40120

n-Heptane

1000000

p-Xylene

1000000

Acetone

1000000

Ethyl acetate

Melting point (°C)

-3

Boiling point (°C)

360

Degradation point (°C)

Flashpoint (°C)

181

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

3.98 X 10⁰⁶

Calculated

Log P

6.6

(EU dossier: LogP 5-6 at pH 2 24 °C; A4)

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.24

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

2.53 X 10^-04

Low volatility

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

2.31 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral solution: 278nm = 2468, 290nm = 765
Acidic solution 278nm = 2472, 290nm = 765
Basic solution: hydrolysis product formed with maxima = 308 nm

Surface tension (mN m⁻¹)

59.5

at 25°C 90% soln

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

56.7

Moderately persistent

DT₉₀ (field)

Note

Earlier EU dossier lab studies DT₅₀ range 6-105 days (A3), DT₉₀ range 34-80.5 days, Current dossier field studies DT₅₀ 6-24 days S. France, Italy and Germany;Other data source: 14 days (DW4)

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

3.05

Moderately fast

Note

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

Value

Non-persistent

Note

pH sensitive: Stable at pH 4, variable at pH 9

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

0.1

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

1033

Non-mobile

K_foc (mL g⁻¹)

121786

¹/_n

1.30

Notes and range

EU dossier K_f range 416-1897 mL g⁻¹, K_foc range 18326-285562 mL g⁻¹, ¹/_n range 1.15-1.47, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.09

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

356

Whole fish

Threshold for concern

CT₅₀ (days)

1.2

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Major fraction

0.242

3-phenoxybenzoic acid

Minor fraction

0.084

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(3-phenoxyphenyl)methanol

mPBAcohol

Plant; Animal

3-phenoxybenzaldehyde

mPBAldehyde

Plant

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)

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5124

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 601 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

2.15

Colinus virginianus

High

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

37.5

Eisenia foetida corr

Moderate

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

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect at 59 days
Carbon mineralisation: No significant adverse effect at 64 days

Dose: 2 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 100

Ryegrass
Vegetative vigour, EC₅₀
as mg kg⁻¹ soil dw

> 100

Ryegrass
Seedling emergence, ER₅₀
as mg kg⁻¹ soil dw

Honeybees (Apis spp.)

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

0.002

Apis mellifera

High

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

0.044

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)

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 mL/ha

5.48

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

23.18

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)

0.00069

Oncorhynchus mykiss

High

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

0.000585

Oncorhynchus mykiss

High

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

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

0.00014

Daphnia magna

High

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

0.00001

Daphnia magna

High

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

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

0.0128

Americamysis bahia

High

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

0.001

Chironomus riparius

High

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

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

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

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

> 1

Pseudokirchneriella subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.26

Rat

Other Mammal toxicity endpoints

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

0.04

Dog SF=200

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

0.125

Rat SF=100

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

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

0.02

Dog SF=400

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Possible risk of exposure to operators or other workers identified - PPE/PPC advised

Mammalian dose elimination route and rate

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

US EPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H302, H317, H332
Environment: H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2902

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

zeta-cypermethrin

French

zetacypermethrine

German

zeta-Cypermethrin

Danish

zeta-cypermethrin

Italian

zeta-cipermetrina

Spanish

zeta-cipermetrin

Greek

Polish

zeta-cypermetryna

Swedish

Hungarian

zeta-cypermethrin

Dutch

Norwegian

Record last updated:	31/07/2024
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