Pyridalyl (Ref: S-1812)

Pyridalyl (Ref: S-1812)	Last updated: 22/08/2024
(Also known as: pyridalil)

SUMMARY

Pyridalyl is an insecticide. It is practically insoluble and slightly volatile. It may be persistent in soil and aquatic systems under certain conditions. It has a low mammalian toxicity, not expected to bioaccumulate and no serious health concerns have been identified. It is highly toxic to all aquatic life

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 High alert: Persistent; Potential for particle bound transport: High	Ecotoxicity High alert: Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A pyridalyl insecticide active against a range of Lepidopterous and Thysanopterous insects

Example pests controlled

Thrips; Caterpillars; Armyworm; Loopers; Gypsy moth; Budworms; Hornworms

Example applications

Ornamental shrubs and flowers; Ornamental tress; Nut trees; Vines; Cotton

Efficacy & activity

Availability status

Current

Introduction & key dates

2002, first reported

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/06/2025

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands

Date EC 1107/2009 inclusion expires

30/06/2025

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

USA

Chemical structure

Isomerism

None

Chemical formula

C₁₈H₁₄Cl₄F₃NO₃

Canonical SMILES

C1=CC(=NC=C1C(F)(F)F)OCCCOC2=C(C=C(C=C2Cl)OCC=C(Cl)Cl)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

AEHJMNVBLRLZKK-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H14Cl4F3NO3/c19-12-9-11(27-8-5-15(21)22)10-13(20)17(12)29-7-2-6-28-16-4-1-3-14(26-16)18(23,24)25/h1,3-5,9-10H,2,6-8H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance groups

Pyridalyl insecticide

Minimum active substance purity

910 g kg⁻¹

Known relevant impurities

Substance origin

Synthetic

Mode of action

Unclear but appears to inhibit insect vigour

CAS RN

179101-81-6

EC number

605-845-4

CIPAC number

792

US EPA chemical code

295149

PubChem CID

11488729

CLP index number

No data found

Molecular mass

491.12

PIN (Preferred Identification Name)

2-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-5-(trifluoromethyl)pyridine

IUPAC name

2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-[5-(trifluoromethyl)-2-pyridyloxy]propyl ether

CAS name

2-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propenyl)oxy]phenoxy]propoxy]-5-(trifluoromethyl)pyridine

Other status information

PAN listed 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

Physical state

Yellow liquid with faint odour

Formulations

Property

Value

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

Valent USA Corporation

Example products using this active

Pyridalyl 10EW
Overture

Formulation and application details

Usually supplied as a wettable powder formulation packaged in water soluble packets containing 35% active ingredient.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.00015

Low

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

Miscible

n-Octanol

Miscible

Xylene

Miscible

Chloroform

Miscible

Acetone

Melting point (°C)

-17

Boiling point (°C)

227

Degradation point (°C)

Flashpoint (°C)

111

(closed cup)

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

1.26 X 10⁰⁸

Calculated

Log P

8.1

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.450

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

6.24 X 10^-05

Low volatility

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

0.205

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

pH 1.1: 208nm=44668, 274nm=4898
pH 7.2-7.9: 208nm=44668, 274nm=4898
pH 10.3: 208nm=44668, 274nm=4786
pH 13.1: 208nm=23998, 274nm=4898;

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

145

Persistent

DT₅₀ (lab at 20 °C)

145

Persistent

DT₅₀ (field)

245

Persistent

DT₉₀ (lab at 20 °C)

30000

Very persistent

DT₉₀ (field)

254

DT₅₀ modelling endpoint

Note

EU Dossier Lab studies DT₅₀ range 53-272 days; DT₉₀ range 465->1000 days; Field studies DT₅₀ range 1.2-39 days, DT₉₀ range 176-350 days; USEPA report Field DT₅₀ range 93.7-346.6 days; General literature DT₅₀ range 93-148 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

3.3

Note

Published literature RL₅₀ range 3.2-3.4 days, 2 field crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Range 2-6 days

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

Value

Stable

Note

Stable pH5 to pH9

Water-sediment DT₅₀ (days)

186

Slow

Water phase only DT₅₀ (days)

8.6

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

1812

Non-mobile

K_foc (mL g⁻¹)

93481

¹/_n

1.04

Notes and range

EU dossier K_f range 1373-2596 mL g⁻¹, K_foc range 52435-171574 mL g⁻¹, ¹/_n range 0.98-1.07, soils=3

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-2.32

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

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

5.6

Calculated using the Atkinson method. Assumed 9.7E+05 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

26858

Whole fish

High potential

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3,5-dichloro-4-(3-((5-(trifluoromethyl)pyridin-2-yl)oxy)propoxy)phenol (Ref: S-1812-DP)

Major fraction

0.122

2-(3-(2,6-dichloro-4-methoxyphenoxy)propoxy)-5-(trifluoromethyl)-pyridine (Ref: S-1812-DP-ME)

Major fraction

0.124

5-(trifluoromethyl)pyridin-2(1H)-one

Major fraction

0.147

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)

5-(trifluoromethyl)pyridin-2(1H)-one

Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propan-1-ol

S-1812-PYP

3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanoic acid

TPPA

1-methyl-5-(trifluoromethyl)pyridin-2(1H)-one

N-methyl-HTFP

3-hydroxy-1-methyl-5-(trifluoromethyl)pyridin-2(1H)-one

N-methyl-HPDO

[3,5-dichloro-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propoxy)phenoxy]acetic acid

S-1812-Ph-CH2-COOH

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

1133 mg kg feed⁻¹

Colinus virginianus

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

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

> 500

Eisenia foetida corr

Moderate

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

31.5

Eisenia foetida corr

Moderate

Soil micro-organisms

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)

> 100

Apis mellifera

Low

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

> 100

Apis mellifera

Low

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

Chronic

Notes

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

457.6

Aphidius rhopalosiphi

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

> 600

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)

0.50

Oncorhynchus mykiss

Moderate

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

0.049

Oncorhynchus mykiss

Moderate

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

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

0.0038

Daphnia magna

High

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

0.0014

Daphnia magna

High

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

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

0.001

Americamysis bahia

High

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

1.10

Chironomus yoshimatsui 48 hr EC₅₀

Moderate

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)

> 0.17

Lemna gibba

Moderate

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

> 0.20

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.01

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.03

Rat SF=100

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

None allocated

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

Rat SF=100

Dermal penetration studies (%)

0.7-3.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk if used in acordance with label guidance

Occupational

Low risk if used in acordance with label guidance

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

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Liver & blood toxicant
May cause thickening of arterial and arteoriole walls

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317, H373
Evironment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

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Name

English

pyridalyl

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Record last updated:	22/08/2024
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