Spirodiclofen (Ref: BAJ 2740)

Spirodiclofen (Ref: BAJ 2740)	Last updated: 06/12/2020
(Not known by any other names)

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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

None (may vary with mixtures)

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
✓		✓	✓	✓	✓		✓

Also used in

Chemical structure

Isomerism

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

No data

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 group

Tetronic acid

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, an inhibitor of lipid biosynthesis

CAS RN

148477-71-8

EC number

CIPAC number

737

US EPA chemical code

124871

PubChem CID

177863

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Tetranychus urticae

Physical state

White powder

Formulations

Property

Value

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

Envidor SC 240

Example products using this active

Bayer CropScience

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)

Not expected to self ignite; Not highly flammable

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

6.76 X 10⁰⁵

Calculated

Log P

5.83

High

Bulk 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^-02

Non-volatile

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

10.1

Note

Citrus fruit, n=1

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

31037

Notes and range

Freundlich

K_f

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.519

Major fraction, Relevant

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

Soil

0.444

Major fraction, Relevant

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

Soil

0.164

Major fraction, Relevant

2,4-dichlorobenzoic acid

Soil

0.396

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-hydroxy-spirodiclofen-enol

Spirodiclofen metabolite M02

Plant

2,4-dichloro-mandelic acid cyclohexyl ester

Spirodiclofen metabolite M09

Animal; Plant

unknown

BAJ 2740-dioxoketone

Water (Photolysis)

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

BAJ 2740-lactide

Soil

4-hydroxy-spirodiclofen-enol

Spirodiclofen metabolite M03

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

491

Threshold for concern

CT₅₀ (days)

0.79

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.035

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.02

Oncorhynchus mykiss 42 day microcosm study

Moderate

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

> 0.051

Daphnia magna

High

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

0.025

Daphnia magna

Moderate

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)

Non-target plants

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

> 0.06

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)

> 200

Low

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

> 196

Low

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)

> 1000

Eisenia foetida

Low

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

2.4

Typhlodromus pyri

% Effect

Parasitism [Dose: 58 g ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 53.3 g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 0.98 mg kg⁻¹ soil 28 days

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)

> 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

Dog 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)

0.009

SF=100

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

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

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
USEPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 3

CLP classification 2013

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

EC Risk Classification

Carcinogen category 3: R40
Xn - Harmful: R43

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Usually 1294

Waste disposal & packaging

Packaging Group II (medium danger)

TRANSLATIONS

Language

Name

English

spirodiclofen

French

spirodiclofen

German

Spirodiclofen

Danish

spirodiclofen

Italian

spirodiclofen

Spanish

espirodiclofen

Greek

Polish

spirodiklofen

Swedish

Hungarian

Dutch

spirodiclofen

Record last updated:	06/12/2020
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