Spirodiclofen (Ref: BAJ 2740)

Spirodiclofen (Ref: BAJ 2740)	Last updated: 24/07/2024
(Not known by any other names)

SUMMARY

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; Daphnia acute ecotoxicity: High	Human health High alert: Carcinogen

GENERAL INFORMATION

Description

A foliar applied acaricide active against a range of sucking insects on fruit and nuts

Example pests controlled

Mites; Pear sucker; Scale insects; Earwigs; Aphids; Whitefly

Example applications

Fruit including apple, pear, grape, peach, apricot, nectarine, orange, currants, citrus, berries; Tomatoes; Cucumber; Almonds; Coconut

Efficacy & activity

Availability status

Current

Introduction & key dates

2000, first reported

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Austria/Netherlands

Date EC 1107/2009 inclusion expires

Expired

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

Iran

Chemical structure

Isomerism

None

Chemical formula

C₂₁H₂₄Cl₂O₄

Canonical SMILES

CCC(C)(C)C(=O)OC1=C(C(=O)OC12CCCCC2)C3=C(C=C(C=C3)Cl)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

DTDSAWVUFPGDMX-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H24Cl2O4/c1-4-20(2,3)19(25)26-17-16(14-9-8-13(22)12-15(14)23)18(24)27-21(17)10-6-5-7-11-21/h8-9,12H,4-7,10-11H2,1-3H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
spirodiclofen	-

General status

Pesticide type

Acaricide, Insecticide

Substance groups

Tetronic acid acaricide; Tetronic acid insecticide

Minimum active substance purity

965 g kg⁻¹

Known relevant impurities

EU dossier - 3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro4.5dec-3-en-2-one (BAJ-2740 enol) 6g kg⁻¹ & N,N-dimethylacetamide 4g kg⁻¹

Substance origin

Synthetic

Mode of action

Selective, non-systemic, distrupts mite development. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

CAS RN

148477-71-8

EC number

604-636-5

CIPAC number

737

US EPA chemical code

124871

PubChem CID

177863

CLP index number

607-730-00-4

Molecular mass

411.32

PIN (Preferred Identification Name)

3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 2,2-dimethylbutanoate

IUPAC name

3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 2,2-dimethylbutyrate

CAS name

3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro(4.5)dec-3-en-4-yl 2,2-dimethylbutanoate

Other status information

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

Tetranychus urticae

Physical state

White to yellow coloured powder

Formulations

Property

Value

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

Bayer CropScience
BOC Sciences

Example products using this active

Envidor SC 240
Envidor Speed

Formulation and application details

Often supplied as a suspension concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.05

Low

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

20000

n-Heptane

250000

Ethyl acetate

250000

Xylene

250000

Dichloromethane

Melting point (°C)

94.8

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

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

1.26 X 10⁰⁵

Calculated

Log P

5.1

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.29

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

3.00 X 10^-04

Low volatility

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

2.00 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

No absorption 300-400nm
Neutral solution 201nm = 37869

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

7.3

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 1.1-13 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

10.0

Note

Citrus fruit; Strawberries, range 9.9-10.1; n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

123

Stable

Note

Data for midday summer conditions at 40 deg N

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

Value

52.1

Moderately persistent

Note

pH sensitive: DT₅₀ 119.6 days at pH 4, 2.5 days at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

3.2

Fast

Water phase only DT₅₀ (days)

0.7

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)

Non-mobile

K_oc (mL g⁻¹)

31037

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.42

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

Potential for loss via drain flow

Non-mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

491

Threshold for concern

CT₅₀ (days)

0.79

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro(4.5)dec-3-en-2-one

Major fraction

0.519

3-(2,4-dichlorophenyl)-3-hydroxy-1-oxaspiro(4.5)decane-2,4-dione

Major fraction

0.444

3-(2,4-dichlorophenyl)-3,4-dihydroxy-1-oxaspiro(4.5)decan-2-one

Major fraction

0.164

2,4-dichlorobenzoic acid

Major fraction

0.396

3-(2,4-dichlorophenyl)-1,4-dioxaspiro[5.5]undecane-2,5-dione

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-hydroxy-spirodiclofen-enol

Spirodiclofen metabolite M02

Plant

2,4-dichloro-mandelic acid cyclohexyl ester glucosylpentoside

Spirodiclofen metabolite M04

Plant

2,4-dichloro-mandelic acid hydroxy-cyclohexyl ester

Spirodiclofen metabolite M05

Plant

2,4-dichloro-mandelic acid

Spirodiclofen metabolite M06

Plant

2,4-dichloro-mandelic acid glucosyl cyclohexyl ester

Spirodiclofen metabolite M07

Plant

2,4-dichloro-mandelic acid glucoside

Spirodiclofen metabolite M08

Animal; Plant

2,4-dichloro-mandelic acid cyclohexyl ester

Spirodiclofen metabolite M09

Animal; Plant

unknown

BAJ 2740-dioxoketone

Surface water (Photolysis)

4-hydroxy-spirodiclofen-enol

Spirodiclofen metabolite M03

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2500

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 6

Rat

High

(ppm diet)

> 70

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

26.2

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1061 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Colinus virginianus NOEL

Moderate

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

> 1000

Eisenia foetida

Low

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

Soil micro-organisms

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

Dose: 0.98 mg kg⁻¹ soil 28 Day

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)

> 200

Apis mellifera

Low

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

> 196

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)

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

2.4

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)

> 0.035

Oncorhynchus mykiss

High

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

0.02

Oncorhynchus mykiss 42 day microcosm study

Moderate

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

0.71

Danio rerio EC₅₀ Embryo

Moderate

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

> 0.051

Daphnia magna

High

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

0.025

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

0.032

Chironomus riparius

Moderate

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)

> 0.06

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)

> 2500

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.03

Rat

Other Mammal toxicity endpoints

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

0.015

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)

0.009

Dermal penetration studies (%)

0.4-3.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified for intended uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=0.045 µg l⁻¹

Mammalian dose elimination route and rate

Metabolised and lost mainly via urine and bile

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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

Possible adrenal gland toxicant
Liver toxicant
US EPA - probable human carcinogen; CLP data - known human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317, H350, H361f, H373
Environment: H410

WHO Classification

III (Slightly hazardous)

UN Number

Not regulated

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Shelf-life is 2 years. Store in a cool and dry place and at 0-4 DegC for short term (days to weeks) or -32 DegC for long term (months to years).

TRANSLATIONS

Language

Name

English

spirodiclofen

French

spirodiclofen

German

Spirodiclofen

Danish

spirodiclofen

Italian

spirodiclofen

Spanish

espirodiclofen

Greek

Polish

spirodiklofen

Swedish

Hungarian

Dutch

spirodiclofen

Norwegian

Record last updated:	24/07/2024
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