Spirotetramat (Ref: BYI 08330)

Spirotetramat (Ref: BYI 08330)	Last updated: 22/08/2024
(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: Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

An insecticide for the control of a wide range of sucking insects on crops such as fruit and potatoes

Example pests controlled

Scale insects; Aphids; Mealybugs; Mites; Whiteflies; Psyllids; Thrips; Spider mites; Leafhoppers

Example applications

Fruit including citrus, mango, apples, pears; Lettuce; Potatoes; Cotton; Vegetables (fruiting, leafy, brassica, tuberous, and corm); Christmas tree plantations

Efficacy & activity

Availability status

Current

Introduction & key dates

2007, registered Tunisia; 2008, registered USA

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2029

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Austria

Date EC 1107/2009 inclusion expires

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

Canada, Morocco, New Zealand, Turkey, USA

Chemical structure

Isomerism

Spirotetramat is a chiral molecule. The technical material is a mixture of two stereoisomers cis-spirotetramat and trans-spirotetramat. It is the cis-isomer that is the active substance.

Chemical formula

C₂₁H₂₇NO₅

Canonical SMILES

CCOC(=O)OC1=C(C(=O)NC12CCC(CC2)OC)C3=C(C=CC(=C3)C)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

CLSVJBIHYWPGQY-GGYDESQDSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H27NO5/c1-5-26-20(24)27-18-17(16-12-13(2)6-7-14(16)3)19(23)22-21(18)10-8-15(25-4)9-11-21/h6-7,12,15H,5,8-11H2,1-4H3,(H,22,23)/t15-,21+/f/h22H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
spirotetramat	-

General status

Pesticide type

Insecticide

Substance groups

Tetramic acid insecticide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Stomach acting, broad spectrum, long acting insecticide that is rapidly translocated. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.

CAS RN

203313-25-1

EC number

606-523-6

CIPAC number

795

US EPA chemical code

392201

PubChem CID

9969573

CLP index number

607-711-00-0

Molecular mass

373.48

PIN (Preferred Identification Name)

(5s,8s)-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate

IUPAC name

cis-4-(ethoxycarbonyloxy)-8-methoxy-3-(2,5-xylyl)-1-azaspiro[4.5]dec-3-en-2-one

CAS name

cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro(4.5)dec-3-en-4-yl ethyl carbonate

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

Physical state

Light beige powder

Formulations

Property

Value

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

Bayer CropScience

Example products using this active

Movento
Ultor
Kontos

Formulation and application details

Usually supplied as a suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

29.9

Low

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

55.0

n-Hexane

600000

Dichloromethane

60000

Toluene

67000

Ethyl acetate

Melting point (°C)

142

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

235

Flashpoint (°C)

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

3.24 X 10⁰²

Calculated

Log P

2.51

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

10.7

Vapour pressure at 20 °C (mPa)

5.6 X 10^-06

Low volatility

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

6.99 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

pH 2: 201nm=26823, 213nm=20704
pH 7: 211nm=22000, 276nm=800
pH 10: 212nm=22418

Surface tension (mN m⁻¹)

61.65

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.19

Non-persistent

DT₅₀ (lab at 20 °C)

0.19

Non-persistent

DT₅₀ (field)

0.7

Non-persistent

DT₉₀ (lab at 20 °C)

0.63

Non-persistent

DT₉₀ (field)

2.2

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 0.05-0.38 days, DT₉₀ range 0.28-1.26 days, Field studies DT₅₀ range 0.3-1.0 days, DT₉₀ range 1.1-3.5 day; Manufacturer published data gives DT₅₀ < 1day

Dissipation rate RL₅₀ (days) on plant matrix

Value

4.3

Note

Published literature RL₅₀ range 1.23-7.34 days, 2 field grown crops, N=2

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

3.7

Note

Published literature RL₅₀ range 1.7-6.6 days,4 field grown crops, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

26.2

Slow

Note

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

Value

8.6

at 25°C

Non-persistent

Note

at pH4: DT₅₀=32.5 days, at pH9 DT₅₀=0.32 days all at 25 °C

Water-sediment DT₅₀ (days)

0.78

Fast

Water phase only DT₅₀ (days)

0.78

Fast

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

[Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study], [Kiwifruit: 24.8-30.1 days; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

4.39

Moderately mobile

K_oc (mL g⁻¹)

289

Notes and range

EU dossier K_d range 3.58-5.52 mL g⁻¹, K_oc range 184-385 mL g⁻¹, soils =5

Freundlich

K_f (mL g⁻¹)

4.08

Moderately mobile

K_foc (mL g⁻¹)

281

¹/_n

0.941

Notes and range

EU dossier K_f range 3.70-4.79 mL g⁻¹, K_foc range 159-435 mL.g, ¹/_n rnage 0.823-1.042, Soils = 5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.24

Calculated

Low leachability

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

Value

2.05 X 10^-04

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

cis-3-(2,5-dimethylphenyl)-3-hydroxy-8-methoxy-1-azaspiro(4.5)decane-2,4-dione

Major fraction

0.24

Bayer verified

2-cis-1-(((2,5-dimethylphenyl)hydroxyacetyl)amino)-4-methoxycyclohexanecarboxylic acid

Minor fraction

0.052

Bayer verified

4-methoxy-cyclohexanone

Major fraction

0.100

Bayer verified

cis-3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1-azaspiro(4.5)dec-3-en-2-one

Major fraction

1.00

Bayer verified

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

spirotetramet-monohydroxy

(5s,8s)-3-[2-(hydroxymethyl)-5-methylphenyl]-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one

spirotetramat-photo--hydroxy-methyl

Surface water

(1s,4s)-8-hydroxy-4-methoxy-5-methyl-2-H-spiro(cyclohexane-1-1indenol[1,2-c]pyrrol)-3(8H)-one

spirotetramat-photo-cyclopentyl

Surface water

ethyl -2[(5s,8s)-8-methoxy-2-oxo-1-azapiro[4.5]dec-3-en-3-yl]-4-methylbenzyl carbonate

spirotetramat-photo-2-methylcarbonate

Surface water

4-methoxy-cyclohexanone

Surface water

(1s,4s)-1-amino-4-methoxycyclohexanecarboxylic acid

4-methoxy-cyclohexyl-aminocarboxylic acid

Surface water

2-((5s,8s)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-yl)-4-methylbenzaldehyde

spirotetramat-photo-formyl

Surface water

spirotetramat-enol-glucoside

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

13.2

Rat

High

(ppm diet)

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

70.7

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 475 mg kg bw⁻¹ day⁻¹

Colinus Virginianus

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

Colinus virginianus NOAEL

Moderate

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

> 1000

Eisenia foetida

Low

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

100

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose 1.3 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

134

Zea mays
Vegetative vigour, ER₅₀
as g ha⁻¹

> 176

Brassica napus
Seedling emergence, ER₅₀
as g ha⁻¹

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)

> 107.3

Apis mellifera

Low

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

Chronic

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

14.7

Aphidius rhopalosiphi

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

0.333

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)

> 2.11

Oncorhynchus mykiss

Moderate

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

0.534

Pimephales promelas 33 day

Moderate

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

> 100

Danio rerio

Low

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

> 42.7

Daphnia magna

Moderate

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

2.0

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)

1.3

Chironomus riparius

Moderate

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)

4.49

Lemna gibba

Moderate

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

0.96

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.18

Rat 4 hr

Other Mammal toxicity endpoints

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

0.05

Rat SF=100

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

1.0

Rat 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)

0.05

Dog SF=100

Dermal penetration studies (%)

0.56-2.15

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Acceptable with PPE/PPC

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

Rapid excretion mainly via the urine - 90% within first 24hrs

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available
Possible liver and kidney toxicant
May cause lung damage

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 9
Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317, H319, H335, H361fd
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

spirotetramat

French

German

Danish

Italian

Spanish

Greek

Polish

spirotetramat

Swedish

spirotetramat

Hungarian

Dutch

Norwegian

spirotetramat

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