Spiroxamine (Ref: KWG 4168)

Spiroxamine (Ref: KWG 4168)	Last updated: 31/10/2024
(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 High alert: Potential for particle bound transport: High	Ecotoxicity High alert: Birds chronic ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A systemic fungicide used to control common fungal diseaases on cereals and fruit

Example pests controlled

Powdery mildew; Leaf spots; Rusts

Example applications

Grapes; Cereals including wheat, triticale; barley, oats, rye

Efficacy & activity

Wheat/Mildew=Low; Wheat/Rust=Low; Barley/Rhynchosporium=Low; Barley/Mildew=Low; Barley/Rust=low; Barley/Net blotch=Low

Availability status

Current

Introduction & key dates

1993, first registered USA

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2031

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria/Estonia

Date EC 1107/2009 inclusion expires

31/05/2026

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

Australia, Morocco

Chemical structure

Isomerism

A chiral molecule. The technical material is an isomeric mixture of four biologically active isomers - two diastereomers, four enantiomers.

Chemical formula

C₁₈H₃₅NO₂

Canonical SMILES

CCCN(CC)CC1COC2(O1)CCC(CC2)C(C)(C)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

PUYXTUJWRLOUCW-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H35NO2/c1-6-12-19(7-2)13-16-14-20-18(21-16)10-8-15(9-11-18)17(3,4)5/h15-16H,6-14H2,1-5H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Morpholine fungicide; Spiroketalamine fungicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with protective, curative and eradicative action. Disrupts membrane function. Inhibits sterol biosynthesis in membranes.

CAS RN

118134-30-8

EC number

601-505-4

CIPAC number

572

US EPA chemical code

120759

PubChem CID

86160

CLP index number

612-150-00-X

Molecular mass

297.5

PIN (Preferred Identification Name)

rac-N-{[(2R)-8-tert-butyl-1,4-dioxaspiro[4.5]decan-2-yl]methyl}-N-ethylpropan-1-amine

IUPAC name

8-tert-butyl-1,4-dioxaspiro[4.5]decan-2-ylmethyl(ethyl)(propyl)amine

CAS name

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro(4.5)decane-2-methanamine

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)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

Pale yellow liquid

Formulations

Property

Value

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

Bayer CropScience
Agrobeats Tech Co. Ltd.

Example products using this active

Cello
Helix
Sage
Torch Extra
Prosper 500 EC

Formulation and application details

Often supplied as an emulsifiable 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)

405

Moderate

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

200000

n-Hexane

200000

Acetone

200000

Methanol

200000

Toluene

Melting point (°C)

-170

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

120

Flashpoint (°C)

147

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

7.76 X 10⁰²

Calculated

Log P

2.89

Moderate

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

0.93

Dissociation constant pKa) at 25 °C

6.9

Base

Vapour pressure at 20 °C (mPa)

5.0

Moderately volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

3.80 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 maximum of absorbance between 200nm - 400nm

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)

22.1

Non-persistent

DT₅₀ (field)

52.4

Moderately persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

175.4

DT₅₀ modelling endpoint

Note

Field studies DT₅₀ range 19.8-145.3 days (normalised), DT₉₀ range 42.9-466.2 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

8.0

Note

Published literature RL₅₀ range 2.0-14.0 days, 2 field crops, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

50.5

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 7, slow hydrolysis at pH 9

Water-sediment DT₅₀ (days)

66.2

Moderately fast

Water phase only DT₅₀ (days)

0.8

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

142.3

Non-mobile

K_foc (mL g⁻¹)

14567

¹/_n

0.821

Notes and range

EU dossier kf range 4.61-892.6mL g⁻¹, K_foc range 658.8-85008 mL g⁻¹, ¹/_n range 0.768-1.063, Soils=10

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.28

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

High

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)

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

N-((8-tert-butyl-1,4-dioxaspiro(4.5)dec-2-yl)methyl)methyl]ethanamine (Ref: Spiroxamine-despropyl)

Minor fraction

0.092

Bayer verified

[(8-tert-butyl-1,4-dioxaspiro[4.5]dec-2-yl)methyl]ethyl(propyl)amine oxide (Ref: N-oxide spiroxamine)

Minor fraction

0.079

Bayer verified

N-((8-tert-butyl-1,4-dioxaspiro(4.5)dec-2-yl)methyl)propan-1-amine (Ref: KWG 4168-desethyl)

Minor fraction

0.088

Bayer verified

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

[(8-tert-butyl-1,4-dioxaspiro[4.5]dec-2-yl)methyl]ethyl(propyl)amine oxide (Ref: N-oxide spiroxamine)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

-
Note: C27H47NO12

spiroxamine hydroxy-N-oxide malonyl glucoside; Metabolite M21

Plant

-
Note: C16H28O7

spiroxamine cyclohexanol glucuronide; Metabolite M22

Rat; Animal

-
Note: C32H62O2

spiroxamine docosanoic acid ester; Metabolite M35

Plant

-
Note: C10H29NO3

spiroxamine cyclohexenol; Metabolite M37

Plant

-
Note: C16H29NO3

spiroxamine N-formyl despropyl; Metabolite M38

Plant

2-(2-{[ethyl(propyl)amino]methyl}-1,4-dioxaspiro[4.5]dec-8-yl)-3-hydroxy-2-methylpropanoic acid
Note: C18H33NO5

spiroxamine hydroxy acid; Metabolite M07

Animal (Liver)

t-butylcyclohexanone
Note: Secondary product

-
Note: C17H31NO3

N-formyl-desethyl spiroxamine; Metabolite M04

Plant

-
Note: C18H35NO3; LD50(oral, rat) = 707 mg/kg bw

N-oxide spiroxamine; Metabolite M03

Rat; Plant

-
Note: C18H35NO6S

spiroxamine sulfate; Metabolite M25

Rat; Animal

-
Note: C16H31NO6S

spiroxamine desethyl sulfate; Metabolite M26

Rat; Animal

-
Note: C15H29NO6S

spiroxamine despropyl sulfate; Metabolite M27

Rat; Animal

-
Note: C8H19NO2

spiroxamine aminodiol; Metabolite M28

Rat; Plant

-
Note: C8H19NO3

spiroxamine aminodiol-N-oxide; Metabolite M29

Plant

-
Note: C6H15NO2

spiroxamine desethyl aminodiol; Metabolite M30

Plant

-
Note: C5H13NO2

spiroxamine despropyl aminodiol; Metabolite M31

Plant

-
Note: C16H30O6

spiroxamine cychohexanol glucoside; Metabolite M32

Plant

2-(2-{[ethyl(propyl)nitroryl]methyl}-1,4-dioxaspiro[4.5]dec-8-yl)-2-methylpropyl hexopyranoside
Note: C15H29NO3

hydroxy-despropyl spiroxamine; Metabolite M09

Plant

-
Note: C18H35NO3

hydroxy spiroxamine; Metabolite M05

Rat; Animal; Plant

-
Note: C18H33NO5

8-hydroxy acid spiroxamine; Metabolite M08

Rat; Animal

-
Note: C10H17O2R

spiroxamine hydroxy ketone conjugate; Metabolite M23

Plant

-
Note: C10H18O2R

spiroxamine diol diglycoside; Metabolite M24

Plant

-
Note: C24H45NO9

spiroxamine hydroxy-N-oxide glucoside; Metabolite M20

Plant

-
Note: C18H35NO4

hydroxy-N-oxide spiroxamine; Metabolite M10

Plant

-
Note: C16H29NO4

desethyl KWG4168; Metabolite M11

Rat; Animal; Plant

-
Note: C15H27NO4

despropyl acid spiroxamine; Metabolite M12

Rat; Plant

-
Note: C10H20O

cyclohexanol spiroxamine; Metabolite M13

Rat; Animal; Plant

-
Note: C10H20O2

spiroxamine diol; Metabolite M14

Plant

-
Note: C10H18O

spiroxamine ketone; Metabolite M15

Rat; Plant

-
Note: C10H18O2

spiroxamine hydroxy ketone; Metabolite M16

Plant

-
Note: C24H41NO10

spiroxamine acid glucuronide; Metabolite M19

Rat; Animal

2-(2-{[ethyl(propyl)amino]methyl}-1,4-dioxaspiro[4.5]dec-8-yl)-2-methylpropanoic acid
Note: C18H33NO4

spiroxamine acid; Metabolite M06

Rat; Animal (Tissue, Milk, Eggs); Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

460

Mouse

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

565

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Anas platyrhynchos

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

5.4

Colinus virginianus NOAEL

High

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

> 500

Eisenia foetida corr

Moderate

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

5.0

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 7.5 l formulation ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

32.0

Folsomia candida

Non-target plants

> 400

Abutilon heophrasti Amanthus retroflexus
Seedling emergence, ER₅₀
as g ha⁻¹

> 1.25

Soybean
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)

4.2

Apis mellifera

Moderate

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

> 100

Apis mellifera

Low

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

Chronic

Notes

[The residual time to 25% mortality (RT25) value for honeybees is 3 hrs - USEPA data]

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

80.1

Aphidius rhopalosiphi

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

240

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)

7.13

Lepomis macrochirus

Moderate

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

0.014

Oncorhynchus mykiss

Moderate

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

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

6.1

Daphnia magna

Moderate

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

0.1

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)

5.6

Chironomus riparius

Moderate

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

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

2.76

Lemna gibba

Moderate

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

0.003

Scenedesmus subspicatus

High

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

0.0002

Unknown species

High

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)

460

Mouse

Moderate

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

1068

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.0

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.025

Dog SF=100

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

0.1

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)

0.015

Rat SF=167

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

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

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

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H302, H312, H315, H317, H332, H373, H261d
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2588

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

spiroxamine

French

spiroxamine

German

Spiroxamine

Danish

spiroxamin

Italian

spiroxamina

Spanish

spiroxamina; espiroxamina

Greek

spiroxamine

Polish

spiroksamina

Swedish

Hungarian

spiroxamin

Dutch

spiroxamine

Norwegian

Record last updated:	31/10/2024
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