Spiromesifen (Ref: BSN 2060)

Spiromesifen (Ref: BSN 2060)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A selective tetronic acid derivative insecticide used on fruit, vegetables and ornamentals

Example pests controlled

Whiteflies; Mites including the two-spotted spidermite, grass mite, broad mite

Example applications

Cucumber; Courgettes; Peppers; Tomatoes; Aubergine; French beans; Melons; Strawberry; Ornamentals including roses, carnations

Efficacy & activity

Availability status

Current

Introduction & key dates

2002, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

30/09/2023

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

USA

Chemical structure

Isomerism

Chemical formula

C₂₃H₃₀O₄

Canonical SMILES

CC1=CC(=C(C(=C1)C)C2=C(C3(CCCC3)OC2=O)OC(=O)CC(C)(C)C)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

BNKLJOYAQLEMKB-UHFFFAOYSA-J

International Chemical Identifier (InChI)

InChI=1S/C23H30O4/c1-14-11-15(2)18(16(3)12-14)19-20(26-17(24)13-22(4,5)6)23(27-21(19)25)9-7-8-10-23/h11-12H,7-10,13H2,1-6H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
spiromesifen	-

General status

Pesticide type

Insecticide

Substance group

Tetronic acid

Minimum active substance purity

965 g kg⁻¹

Known relevant impurities

EU dossier - N,N-dimethylacetamide <4 g kg⁻¹

Substance origin

Synthetic

Mode of action

Non-systemic. Inhibitors of lipid synthesis.

CAS RN

283594-90-1

EC number

CIPAC number

747

US EPA chemical code

024875

PubChem CID

9907412

Molecular mass

370.48

PIN (Preferred Identification Name)

2-oxo-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4.4]non-3-en-4-yl 3,3-dimethylbutanoate

IUPAC name

3-mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-yl 3,3-dimethylbutyrate

CAS name

2-oxo-3-(2,4,6-trimethylphenyl)-1-oxaspiro(4.4)non-3-en-4-yl 3,3-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

Colourless crystals

Formulations

Property

Value

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

Oberon

Example products using this active

Bayer CropScience
Certis

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)

0.13

Low

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

23000

n-Heptane

250000

Xylene

250000

Acetone

250000

Ethyl acetate

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

375

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.55 X 10⁰⁴

Calculated

Log P

4.55

High

Bulk density (g ml⁻¹)

1.13

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

7.00 X 10^-03

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

Neutral solution: 214nm = 23400, no significant absorbance >290 nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

4.1

Non-persistent

DT₅₀ (lab at 20 °C)

4.1

Non-persistent

DT₅₀ (field)

2.1

Non-persistent

DT₉₀ (lab at 20 °C)

13.8

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 1.9-10.6days, DT₉₀ range 6.3-56.7 days; field data for California

Dissipation rate RL₅₀ on plant matrix

Value

4.1

Note

Published literature RL₅₀ range 1.2-7.1 days, 2 field grown crops, various matrices, n=2

Dissipation rate RL₅₀ on and in plant matrix

Value

2.0

Note

Published literature RL₅₀ range 0.4-3.7 days, 4 field grown crops, various matrices, n=5

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.7

Moderately fast

Note

Data for test conditions and is equivalent to a DT₅₀ of 5.8 days in midsummer, Arizona USA (33 deg N)

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

Value

44.7

Moderately persistent

Note

pH sensitive: DT₅₀ 107.3 days at pH 4, 4.8 days at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

5.95

Fast

Water phase only DT₅₀ (days)

0.15

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

30900

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

-0.16

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

4-hydroxy-3-mesityl-1-oxaspiro(4.4)non-3-en-2-one

Soil

0.850

Major fraction, Relevant

4-(8-hydroxy-6-oxo-5-oxaspiro[3.4]oct-7-en-7-yl)-3,5-dimethylbenzoic acid

Soil

0.141

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-hydroxymethyl-BSN 0546

spiromesifen metabolite M02

Rat (Urinary, Faeces); Plant

4-hydroxymethyl-3-hydroxy-BSN 0546

spiromesifen metabolite M05

Plant

3-hydroxy-BSN 0546

spiromesifen metabolite M06

Plant

dihydroxy-BSN 0546

spiromesifen metabolite M04

Rat; Plant

spiromesifen metabolite M03

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

545

Threshold for concern

CT₅₀ (days)

0.7

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

> 30

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

14.2

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Unknown species

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

23.2

Anas platyrhynchos NOED

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.016

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.0047

Oncorhynchus mykiss

High

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

> 0.092

Daphnia magna

Moderate

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

0.00025

Daphnia magna

High

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)

0.1

Chironomus riparius

Moderate

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

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

0.101

Lemna gibba 7 day

Moderate

Non-target plants

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

> 0.094

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)

> 792.4

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)

4.32

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

40.63

as mL product ha⁻¹ (Oberon SC: Conc 240 g l⁻¹)
Aphidius rhopalosiphi

% Effect

-2.7 / 97.3

Mortality / Fecundity [Dose: 0.864 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

68.4

7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 2.96 mg kg⁻¹ soil

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.87

Rat

Other Mammal toxicity endpoints

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

0.03

Mouse SF=100

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

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)

0.015

Mouse SF=100

Dermal penetration studies (%)

3.0

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

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

Eye irritant

Phototoxicant

No data found

General human health issues

Liver, uterus, adrenal gland and thyroid are target organs

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317, H332
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S24, S37

WHO Classification

NL (Not listed)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

spiromesifen

French

spiromesifen

German

Spiromesifen

Danish

spiromesifen

Italian

spiromesifen

Spanish

spiromesifen

Greek

Polish

spiromesifen

Swedish

Hungarian

Dutch

spiromesifen

Record last updated:	12/01/2021
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