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spiroxamine (Ref: KWG 4168)
** Translations

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GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for spiroxamine

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: -

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Austria/Estonia
Date inclusion expires 31/12/2021
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia

Chemical structure: Click here for further information on the general chemical status information used on this site
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 No data
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
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Morpholine
Minimum active substance purity 950 g/kg
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 -
CIPAC number 572
US EPA chemical code 120759
PubChem CID 86160
Molecular mass (g mol-1) 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 Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) 5
Examples of recorded resistance -
Physical state Pale yellow liquid
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Bayer CropScience
Example products using this active
  • Cello
  • Helix
  • Sage
  • Torch Extra
  • Prosper 500 EC
UK LERAP status LERAP Category B (may vary with mixtures)
Formulation and application details Often supplied as an emulsifiable concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE

for spiroxamine

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 405 A5 Moderate
Solubility - In organic solvents at 20oC (mg l-1) 200000 A5 - n-Hexane -
200000 A5 - Acetone -
200000 A5 - Methanol -
200000 A5 - Toluene -
Melting point (oC) -170 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 120 A5 -
Flashpoint (oC) 147 A5 -
Octanol-water partition coefficient at pH 7, 20oC P 7.76 X 1002 Calculated -
Log P 2.89 A5 Moderate
Bulk density (g ml-1)/Specific gravity 0.93 A5 -
Dissociation constant (pKa) at 25oC 6.9 A5 -
Note: Base
Vapour pressure at 20oC (mPa) 3.5 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 3.80 X 10-03 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -0.25 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index 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 Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 No maximum of absorbance between 200nm - 400nm A5 -
Surface tension (mN m-1) - - -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 25 A5 Non-persistent
DT50 (lab at 20oC) 35 A5 Moderately persistent
DT50 (field) 57.5 A5 Moderately persistent
DT90 (lab at 20oC) 100 A4 -
DT90 (field) 153 A5 -
DT50 modelling endpoint - - -
Note Field studies DT50 range 19.8-145.3 days, DT90 range 42.9-466.2 days
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value 14.1 R3 -
Note Grape berries, n=1
Aqueous photolysis DT50 (days) at pH 7 Value 50.5 A5 Stable
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 7, slow hydrolysis at pH 9
Water-sediment DT50 (days) 66.2 A5 Moderately fast
Water phase only DT50 (days) 0.8 A5 Fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 142.3 A5 Non-mobile
Kfoc 14567
1/n 0.821
Notes and range EU dossier kf range 4.61-892.6mL/g, Kfoc range 658.8-85008 mL/g, 1/n range 0.768-1.063, Soils=10
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
N-((8-tert-butyl-1,4-dioxaspiro(4.5)dec-2-yl)methyl)propan-1-amine Soil   0.088   Minor fraction, Not relevant
N-((8-tert-butyl-1,4-dioxaspiro(4.5)dec-2-yl)methyl)methyl]ethanamine Soil   0.092   Minor fraction, Not relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
- spiroxamine sulfate; Metabolite M25 Rat; Animal - -
- spiroxamine desethyl sulfate; Metabolite M26 Rat; Animal - -
- spiroxamine despropyl sulfate; Metabolite M27 Rat; Animal - -
- spiroxamine aminodiol; Metabolite M28 Rat; Plant - -
- spiroxamine aminodiol-N-oxide; Metabolite M29 Plant - -
- spiroxamine desethyl aminodiol; Metabolite M30 Plant - -
- spiroxamine despropyl aminodiol; Metabolite M31 Plant - -
- 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 - -
- hydroxy-N-oxide spiroxamine; Metabolite M10 Plant - -
- desethyl KWG4168; Metabolite M11 Rat; Animal; Plant; Soil - -
- despropyl acid spiroxamine; Metabolite M12 Rat; Plant; Soil - -
- cyclohexanol spiroxamine; Metabolite M13 Rat; Animal; Plant - -
- spiroxamine diol; Metabolite M14 Plant - -
- spiroxamine ketone; Metabolite M15 Rat; Plant; Soil - -
- spiroxamine hydroxy ketone; Metabolite M16 Plant - -
- spiroxamine acid glucuronide; Metabolite M19 Rat; Animal - -
- spiroxamine hydroxy-N-oxide glucoside; Metabolite M20 Plant - -
- spiroxamine hydroxy-N-oxide malonyl glucoside; Metabolite M21 Plant - -
- spiroxamine cyclohexanol glucuronide; Metabolite M22 Rat; Animal - -
- spiroxamine docosanoic acid ester; Metabolite M35 Plant - -
- spiroxamine cyclohexenol; Metabolite M37 Plant - -
- 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
- - - -
- N-formyl-desethyl spiroxamine; Metabolite M04 Plant - -
- N-oxide spiroxamine; Metabolite M03 Rat; Plant; Soil 0.110 -
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; Soil - -
- hydroxy spiroxamine; Metabolite M05 Rat; Animal; Plant; Soil - -
- 8-hydroxy acid spiroxamine; Metabolite M08 Rat; Animal - -
- spiroxamine hydroxy ketone conjugate; Metabolite M23 Plant - -
- spiroxamine diol diglycoside; Metabolite M24 Plant - -


ECOTOXICOLOGY

for spiroxamine

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 79 A5 Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) 460 A5 Mouse Moderate
Mammals - Short term dietary NOEL (mg kg-1) - A5 Rat -
(ppm diet) 30 -
Birds - Acute LD50 (mg kg-1) 565 A5 Colinus virginianus Moderate
Birds - Short term dietary (LC50/LD50) > 5000 mg kg feed-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 7.13 A5 Lepomis macrochirus Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.014 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 6.1 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.1 A5 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) 3.2 A5 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 C4 Lemna gibba Moderate
Non-target plants > 400 A5 Abutilon heophrasti, Amanthus retroflexus
Seedling emergence, ER50
as g/ha
-
> 1.25 A5 Soybean
Seedling emergence, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 0.003 A5 Scenedemus subspicatus High
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.0002 Q2 Unknown species High
Honeybees Contact acute 48 hour LD50 (μg bee-1) 4.2 A5 Moderate
Oral acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 1000 A5 Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 240 A5 Typhlodromus pyri -
% Effect 77 Mortality
Dose: 0.75 kg ha-1
A5 Aphidius rhopalosiphi, pupae
-
Other arthropod (2) LR50 g ha-1 80.1 A5 Aphidius rhopalosiphi -
% Effect 99 Mortality
Dose: 0.74 kg ha-1
A5 Typhlodromus pyri
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 7.5 l formulation ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for spiroxamine

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) 460 A5 Mouse Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) 1068 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 2.0 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.025 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.1 A5 Rat, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.015 A3 Rat, SF=167 -
Dermal penetration studies (%) 100 A3 default -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public No unacceptable risks to bystanders identified
Occupational No unacceptable risks to operators or other workers identified
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

General human health issues No further information available

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 6.1
CLP classification 2013 Health: H302, H312, H315, H317, H332
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R20/21/22, R43
Xi - Irritant: R38
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S36/37/39, S46, S60, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II - Warning - Moderately toxic
UN Number Usually 2902
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for spiroxamine

Language Name
English spiroxamine
French spiroxamine
German Spiroxamine
Danish spiroxamin
Italian spiroxamina
Spanish spiroxamina; espiroxamina
Greek spiroxamine
Slovenian spiroxamin
Polish spiroksamina
Swedish -
Hungarian spiroxamin
Dutch spiroxamine

Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk
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