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spiromesifen (Ref: BSN 2060)
** Translations

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

Description: An 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

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK
Date inclusion expires 30/09/2023
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: USA

Chemical structure: Click here for further information on the general chemical status information used on this site
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
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Insecticide
Substance group Tetronic acid
Minimum active substance purity 965 g/kg
Known relevant impurities EU dossier - N,N-dimethylacetamide <4 g/kg
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 (g mol-1) 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) 23
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Tetranychus urticae
Physical state Colourless crystals
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
  • Certis
Example products using this active
  • Oberon
UK LERAP status None
Formulation and application details Often supplied as a suspension concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE

for spiromesifen

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) 0.13 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 23000 A5 - n-Heptane -
250000 A5 - Xylene -
250000 A5 - Acetone -
250000 A5 - Ethyl acetate -
Melting point (oC) 98 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 375 A3 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 3.55 X 1004 Calculated -
Log P 4.55 A5 High
Bulk density (g ml-1)/Specific gravity 1.13 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 7.00 X 10-03 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 2.00 X 10-02 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -0.30 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 Neutral solution: 214nm = 23400, no significant absorbance >290 nm 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) 4.1 A5 Non-persistent
DT50 (lab at 20oC) 4.1 A5 Non-persistent
DT50 (field) 2.1 P4 Non-persistent
DT90 (lab at 20oC) 13.8 A5 -
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 2. - -
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 Published literature RL50 range 0.4-3.7 days, 4 field grown crops, various matrices, n=5 - -
Note R4
Aqueous photolysis DT50 (days) at pH 7 Value 1.7 A5 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 20oC and pH 7 Value 44.7 A5 Moderately persistent
Note pH sensitive: DT50 107.3 days at pH 4, 4.8 days at pH 9, all at 20 degC
Water-sediment DT50 (days) 5.95 A5 Fast
Water phase only DT50 (days) 0.15 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 - A4 Non-mobile
Koc 30900
Notes and range -
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
4-hydroxy-3-mesityl-1-oxaspiro(4.4)non-3-en-2-one This metabolite may cause environmental pollution, click here for further information Soil   0.850   Major fraction, Relevant
4-(8-hydroxy-6-oxo-5-oxaspiro[3.4]oct-7-en-7-yl)-3,5-dimethylbenzoic acid This metabolite may cause environmental pollution, click here for further information 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

for spiromesifen

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) 545 A5 Threshold for concern
CT50 (days) 0.7 -
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - A5 Rat -
(ppm diet) > 30 -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 5000 mg kg feed-1 A4 Unknown species -
Fish - Acute 96 hour LC50 (mg l-1) 0.016 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.0047 A5 Oncorhynchus mykiss High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 0.092 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.00025 A5 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 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) 0.101 F3 Lemna gibba, 7 day Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 0.094 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 200 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 792.4 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 1000 A5 Eisenia foetida Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 4.32 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 40.63 as mL product ha-1 (Oberon SC: Conc 240 g/L)
A5 Aphidius rhopalosiphi
-
% Effect -2.7
97.3
Mortality
Fecundity
Dose: 0.864 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 68.4 7 day
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 2.96 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for spiromesifen

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) > 2000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 4.87 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.03 A5 Mouse, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 2 A5 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 A2 Mouse, SF=100 -
Dermal penetration studies (%) 3.0 A5 -
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) 0.1 A5 -

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 Liver, uterus, adrenal gland and thyroid are target organs

: 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
IMDG Transport Code is usually 9
CLP classification 2013 None allocated at this time
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R43
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S24, S37
WHO Classification NL - Not listed
US EPA Classification (formulation) No consensus across products or no products available - -
UN Number Usually 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for spiromesifen

Language Name
English spiromesifen
French spiromesifen
German Spiromesifen
Danish spiromesifen
Italian spiromesifen
Spanish spiromesifen
Greek -
Slovenian spiromesifen
Polish spiromesifen
Swedish -
Hungarian -
Dutch spiromesifen

Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk
© University of Hertfordshire