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metaflumizone (Ref: BAS 320l)
** NNI 0250 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
Further data may be found in the VSDB

SUMMARY

Metaflumizone is a semicarbazone broad-spectrum insecticide that is a mixture of E/Z-isomers. It has a low aqueous solubility, is non-volatile and a low potential for leaching to groundwater based on its chemical properties. It is persistent in soil and in water-sediment systems. It has a low mammalian toxicity and considered to have potential negative reproduction/developmental effects. It also has a high potential for bioaccumulation. It has a low to moderate toxicity to most birds, aquatic species, honeybees and earthworms.

GENERAL INFORMATION
for metaflumizone

Description: An insecticide active against key insect pests including Lepidoptera, Coleoptera, Hymenoptera, Isoptera and Diptera. Also has some veterinary applications.

Introduction: 2008, developed.

EC Regulation 1107/2009 (repealing 91/414):
Status Pending
Dossier rapporteur/co-rapporteur UK
Date inclusion expires -

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: USA

General status:
Pesticide type Insecticide, Veterinary substance
Substance group Semicarbazone
Substance origin Synthetic
Mode of action Broad-spectrum, attacks insect nervous system causing paralysis
CAS RN 139968-49-3
EC number -
CIPAC number 779
US EPA chemical code 281250
Chiral molecule Chiral or specific isomer of chiral molecule
Chemical formula C24H16F6N4O2
SMILES -
International Chemical Identifier (InChI) InChI=1/C24H16F6N4O2/c25-23(26,27)18-3-1-2-17(13-18)21(12-15-4-6-16(14-31)7-5-15)33-34-22(35)32-19-8-10-20(11-9-19)36-24(28,29)30/h1-11,13H,12H2,(H2,32,34,35)/f/h32,34H
Structure diagram/image available? Yes
Molecular mass (g mol-1) 506.40
PIN (Preferred Identification Name) -
IUPAC name (EZ)-2'-[2-(4-cyanophenyl)-1-(α,α,α-trifluoro-m-tolyl)ethylidene]-4-(trifluoromethoxy)carbanilohydrazide
CAS name 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(trifluoromethoxy)phenyl]hydrazinecarboxamide
Other status information -
Herbicide Resistance Classification (HRAC) Not applicable
Insecticide Resistance Classification (IRAC) 22B
Fungicide Resistance Classification (FRAC) Not applicable
Physical state White powder
Related substances & organisms

Formulations:
Property Value
Example manufacturers & suppliers of products using this active
  • BASF
Example products using this active
  • ProMeris
  • Alverde
  • Siesta
UK LERAP status No UK approval for use or outside scope
Formulation and application details Usually supplied as a bait formulation or as spot-on solutions.


ENVIRONMENTAL FATE

for metaflumizone

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 0.0018 R4 Low
Solubility - In organic solvents at 20oC (mg l-1) 85 A5 - n-Hexane -
4000 A5 - Toluene -
153300 A5 - Acetone -
14100 A5 - Methanol -
Melting point (oC) 133 A4 - Isomer specific -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 232 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 3.98 X 1004 Calculated -
Log P 4.6 A5 - mean of isomers High
Bulk density (g ml-1)/Specific gravity 1.46 R4 -
Dissociation constant (pKa) at 25oC n/a A5 -
Note: No dissociation
Vapour pressure at 25oC (mPa) 2.32 X 10-08 A5 - mean of isomers Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 0.11 A5 - Z-isomer Moderately volatile
Henry's law constant at 20oC (dimensionless) 2.68 X 10-09 Calculated Non-volatile
GUS leaching potential index -1.05 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 - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 Max @ 234nm=38100, 280nm=19300 A5 -
Surface tension (mN m-1) 70.5 A5 0.01% solution -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 141 A5 Persistent
DT50 (lab at 20oC) 141 A5 Persistent
DT50 (field) 13.8 A5 Non-persistent
DT90 (lab at 20oC) 362 A5 -
DT90 (field) 67.8 A5 -
Note EU dossier lab studies DT50 range 65-376 days, DT90 range 153-728 days, Field studies DT50 range 3.9-53.3 days, DT90 range 9.9-114 days; Manufacturers published data DT50 range 4.3-27 days
Aqueous photolysis DT50 (days) at pH 7 Value 3.28 A4 Moderately fast
Note EU dossier states DT50 2.43-4.12 days
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value ND A3 Very persistent
Note EU dossier States DT50 5-6 days @ pH 4
Water-sediment DT50 (days) 451 A5 Stable
Water phase only DT50 (days) 1.0 A5 Moderately fast

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd 529 A5 Non-mobile
Koc 30714
Notes and range EU dossier Kd range 299-1030 mL/g, Koc range 16500-51000 mL/g
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity -

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
4-(5-hydroxy-3-oxo-4(4-(trifluoromethoxy)phenyl)-6-(3-trifluoromethyl)phenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-5-yl)benzonitrile (Ref: M320I23) Soil   0.081   Minor fraction, Relevant
benzonitrile carboxylic acid (Ref: M320I06) Soil   0.084   Minor fraction, Relevant
m-trifluoromethyl benzoic acid (Ref: M320I29) Soil   ).211   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
- M320I18 Rat - -
- M320I19 Rat - -
- M320I20 Rat - -
- M320I21 Rat - -
- M320I22 Animal - -
- M320I24 Animal - -
- M320I25 Animal; Hen - -
- M320I26 Animal; Hen - -
- M320I27 Hen - -
(Ref: CL1023720) M320I10 Rat; Animal - -
(Ref: CL1023721) M320I11 Rat - -
(Ref: CL1023722) M320I12 Rat - -
(Ref: CL1023723) M320I14 Rat - -
(Ref: CL1023724) M320I15 Rat - -
(Ref: CL1023725) M320I16 Rat - -
(Ref: CL1023726) M320I17 Rat; Animal - -
(Ref: CL1500789) M320I07 Rat; Animal; Plant; Soil - -
(Ref: CL269463) M320I13 Rat; Animal - -
2-(2-oxo-2-(3-trifluoromethyl)phenyl)ethyl)-benzonitrile
(Ref: CL397864)
Note: Cas no: 146653-56-7
M320I04 Rat; Animal; Plant; Soil; Water; Sediment - -
(Ref: CL397865) M320I09 Soil; Water; Sediment - -
trifluoro-methoxy aniline
(Ref: CL65504)
M320I05 Rat; Plant; Soil; Water; Sediment - -
(Ref: CL952480) M320I08 Soil; Water; Sediment - -


ECOTOXICOLOGY

for metaflumizone

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 7800 A5 Lepomis macrochirus High potential
CT50 (days) 14 -
Bioaccumulation potential - Calculated High
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2025 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) > 0.228 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) - - -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 0.331 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 1.47 A5 Daphnia magna -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) > 289 A5 Americamysiss bahia Low
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) 1.8 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 0.0256 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) - - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 0.311 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees - Acute 48 hour LD50 (μg bee-1) 1.65 A5 Contact Moderate
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 , corr Moderate
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 3.25 Mortality as formulation
A5 Typhlodromus pyri
Harmful at 1 kg ha-1
Harmful at 0.1 kg ha-1
Moderately harmful at 0.01 kg ha-1
% Effect - - -
Other arthropod (2) LR50 g ha-1 0.0145 Mortality as formulation
A5 Aphidius rhopalosiphi
Harmful at 1 kg ha-1
Harmful at 0.1 kg ha-1
Harmful at 0.01 kg ha-1
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.2 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for metaflumizone

General:
Property Value Source/Quality Score/Other Information Interpretation
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.2 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.03 A5 Dog, SF=100x2 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.13 A5 Rat, SF=100x3 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.01 A5 Dog, SF=100x17% -
Dermal penetration studies (%) 0.2-0.4 A5 concentration dependant -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public -
Occupational -
Examples of European MRLs (mg kg-1) Value -
Note For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

General human health issues Liver toxicant

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

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Warning: H373, H319
Environment: H400, H410
EC Risk Classification Xn - Harmful: R48/22
Xi - Irritant: R36
N - Dangerous for the environment: R50/53
EC Safety Classification S35, S57, S60, S61
WHO Classification NL - Not listed
US EPA Classification (formulation) No consensus across products or no products available - -
UN Number 3082
Waste disposal & packaging Packaging group III (minor danger)


TRANSLATIONS

for metaflumizone

Language Name
English metaflumizone
French metaflumizone
German Metaflumizon
Danish metaflumizon
Italian metaflumizone
Spanish metaflumizon
Greek -
Slovenian metaflumizon
Polish metaflumizon
Swedish -
Hungarian -
Dutch -

Record last updated: Wednesday 12 March 2014
Contact: aeru@herts.ac.uk