Spirotetramat (Ref: BYI 08330)

Spirotetramat (Ref: BYI 08330)	Last updated: 02/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

New 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, Tunisia; 2008, USA

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria

Date EC 1107/2009 inclusion expires

30/04/2024

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

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

No data

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 group

Tetramic acid

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, inhibition of lipogenesis in treated insects

CAS RN

203313-25-1

EC number

CIPAC number

795

US EPA chemical code

392201

PubChem CID

9969573

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

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

Movento
Ultor
Kontos

Example products using this active

Bayer CropScience

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)

Not expected to self ignite; Not highly flammable

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

3.24 X 10⁰²

Calculated

Log P

2.51

Low

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

3.0

Note

Published literature RL₅₀ range 1.7-4.3 days, field grown eggplant & mango fruits, n=2

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

4.39

Moderately mobile

K_oc

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

4.08

Moderately mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.546

Major fraction, Relevant

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

Soil

0.24

Major fraction, Relevant

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

Soil

0.052

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-methoxy-cyclohexanone

Soil; Water

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

4-methoxy-cyclohexyl-aminocarboxylic acid

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

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

Water

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

spirotetramat-photo-formyl

Water

spirotetramat-enol-glucoside

spirotetramet-monohydroxy

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

spirotetramat-photo--hydroxy-methyl

Water

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

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⁻¹ BW/day

Colinus Virginianus

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

Colinus virginianus NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.96

Cyprindon variegatus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.534

Pimephales promelas 33 day

Moderate

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

> 42.7

Daphnia magna

Moderate

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

2.0

Daphnia magna

Moderate

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

Non-target plants

134

Zea mays
Vegetative vigour, ER₅₀
as g ha⁻¹

> 176

Brassica napus
Seedling emergence, ER₅₀
as g ha⁻¹

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

0.96

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)

> 100

Low

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

> 107.3

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)

100

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

0.333

Mortality
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

114.7

Mortality
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose 1.3 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)

> 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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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

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

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 9
Not explosive or oxidising

CLP classification 2013

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

EC Risk Classification

Reproduction risk category 2 and 3: R61, R62
Xn - Harmful: R43
Xi - Irritant: R36

EC Safety Classification

WHO Classification

III (Slightly hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

spirotetramat

French

German

Danish

Italian

Spanish

Greek

Polish

spirotetramat

Swedish

spirotetramat

Hungarian

Dutch

Record last updated:	02/01/2021
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