Cis-permethrin (Ref: FMC 35171)-Pesticide database

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Cis-permethrin (Ref: FMC 35171)

(Also known as: NRDC 148; NRDC 167; cis-permethrin)

Cispermethrin is an obsolete insecticide. It has not been extensively studied and so very little data for environmental fate, ecotoxiocity of adverse human health concerns are available.

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
	Ecotoxicity High alert: Daphnia acute ecotoxicity: High Warning: Significant data are missing	Human health High alert: Endocrine distrupter; Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

An insecticide which is a component of permethrin, active against a wide range of pests including Lepidoptera and Coleoptera in crops and various animal ectoparasites

Example pests controlled

Cockroaches; Termites; Ticks; Mosquitoes; Aphids; Fleas; Ants

Example applications

Fruit; Vegetables; Cotton; Ornamentals; Potatoes; Cereals

Efficacy & activity

Availability status

Considered obsolete but may be available in some countries

Introduction & key dates

UK regulatory status

UK COPR regulatory status

Date COPR inclusion expires

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

EU Candidate for substitution (CfS)

Listed in EU database

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

Chemical structure

Chemical formula

C₂₁H₂₀Cl₂O₃

Canonical SMILES

CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

Isomeric SMILES

CC1([C@@H]([C@@H]1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

International Chemical Identifier key (InChIKey)

RLLPVAHGXHCWKJ-IEBWSBKVSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3

2D structure diagram/image available?

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cis-permethrin	-

Substance groups

Pyrethroid insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Broad spectrum with contact and stomach action. Slight repellant effect. Sodium channel modulator.

Alternative/old CAS RN

52341-33-0; 54774-45-7; 54774-46-8

US EPA chemical code

CLP index number

PIN (Preferred Identification Name)

3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

rel-(1R,3R)-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Colourless crustalline solid

Related substances & organisms

permethrin

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

Example products using this active

Obsolete - not thought to be commercially available for crop protection applications

Formulation and application details

Was available in a variety of formulations including fumigants, shampoos and spot-on treatments.

ENVIRONMENTAL FATE

Source; quality score; and other information

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

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

Melting point (°C)

Boiling point (°C)

Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source

Degradation point (°C)

Flashpoint (°C)

Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source

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

Fat solubility of residues

Density (g ml⁻¹)

Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

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

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

Surface tension (mN m⁻¹)

Source; quality score; and other information

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Dissipation rate RL₅₀ on plant matrix

Dissipation rate RL₅₀ on and in plant matrix

Aqueous photolysis DT₅₀ (days) at pH 7

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

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Source; quality score; and other information

Notes and range

Notes and range

Source; quality score; and other information

GUS leaching potential index

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Cannot be calculated

Potential for particle bound transport index

Potential for loss via drain flow

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known metabolites

None

Terrestrial ecotoxicology

Source; quality score; and other information

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Mammals - Short term dietary NOEL

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

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

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

Soil micro-organisms

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)

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

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 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)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Source; quality score; and other information

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source

Danio rerio 7 day

Aquatic invertebrates - Chronic 21 day NOEC (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)

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)

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

Mesocosm study data

NOEAEC mg l⁻¹

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

Source; quality score; and other information

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

EU MRL pesticide database

GB MRL Register

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Specific human health issues

Endocrine disruptor

?Possibly, status not identified

A0 A = Chromosome aberration (EFSA database)
0 = No data

B0 B = DNA damage/repair (EFSA database)
0 = No data

C0 C = Gene mutation (EFSA database)
0 = No data

D0 D = Genome mutation (EFSA database)
0 = No data

E2 E = Unspecified genotoxicity type (miscellaneous data source)
2 = Mixed/ambiguous results

✓Yes, known to cause a problem

Reproduction / development effects

Acetyl cholinesterase inhibitor

✓Yes, known to cause a problem

✓Yes, known to cause a problem

Respiratory tract irritant

Skin sensitiser

✓Yes, known to cause a problem

✓Yes, known to cause a problem

General human health issues

A poison by intravenous & intraperitoneal routes
Inhalation may produce nausea, vomiting, sneezing & serious nasal problems
High dose may cause hyperexcitability, incoordination, tremors, muscular paralysis & lead to death

Handling issues

Value and interpretation

IMDG Transport Hazard Class 9

CLP classification 2013

WHO Classification

II (Moderately hazardous)

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

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