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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. Also has some veterinary applications.

Example pests controlled: Lepidoptera; Coleoptera; Hymenoptera; Isoptera; Diptera

Example applications: Cotton; Potatoes; Greenhouse tomatoes & peppers;

Availability status: Current

Introduction & key dates: 2008, developed

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK
Date inclusion expires 31/12/2024

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

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: USA

General status:
Pesticide type Insecticide, Veterinary substance
Substance group Semicarbazone
Minimum active substance purity 945 g/kg
Known relevant impurities EU dossier - hydrazine <1mg/kg; toluene <2mg/kg; 4-(trifluoromethoxy)phenyl isocyanate < 100mg/kg
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 No
Chemical formula C24H16F6N4O2
SMILES C(=N/NC(Nc1ccc(cc1)OC(F)(F)F)=O)(\Cc1ccc(cc1)C#N)c1cc(C(F)(F)F)ccc1
International Chemical Identifier key (InChIKey) MIFOMMKAVSCNKQ-QNKGDIEWSA-N
International Chemical Identifier (InChI) InChI=1S/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 PAN listed Highly Hazardous Chemical
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) 22B
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state White powder
Related substances & organisms

Formulations:
Property Value
Example manufacturers & suppliers of products using this active now or historically
  • 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
Foliar DT50 (days) Value - - -
Note -
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   0.211   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
- M320I19 Rat - -
- M320I20 Rat - -
- M320I21 Rat - -
- M320I22 Animal - -
- M320I24 Animal - -
- M320I25 Animal; Hen - -
- M320I26 Animal; Hen - -
- M320I27 Hen - -
- M320I18 Rat - -
(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 (l kg-1) 7800 A5 Lepomis macrochirus High potential
CT50 (days) 14 -
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 Moderate
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) - - -
Non-target plants - - -
- - -
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 Contact acute 48 hour LD50 (μg bee-1) 1.65 A5 Moderate
Oral acute 48 hour LD50 (μg bee-1) 2.43 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
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 as L product ha-1 (BAS 320 00 I: Conc 240 g l-1)
A5 Typhlodromus pyri
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 0.0145 as L product ha-1 (BAS 320 00 I: Conc 240 g l-1)
A5 Aphidius rhopalosiphi
-
% 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
Threshold of Toxicological Concern (Cramer Class) High (class III) - -
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 -
European MRLs Click here for the EU MRL pesticide database
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 Liver toxicant

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

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 None allocated at this time
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: Friday 11 March 2016
Contact: aeru@herts.ac.uk