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flubendiamide (Ref: NNI-0001)
** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

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

Description: A new broad spectrum insecticide for use in wide range of annual and perennial crops.

Example pests controlled: Various Lepidopterous spp. including armyworms, corn borers, cutworms, diamondback moths, loopers

Example applications: Corn; Cotton; Tobacco; Fruit including apples pears, stone fruit; Nuts; Grapes; Various vegetables

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1979, first reported

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Greece
Date inclusion expires 31/08/2024
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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C23H22F7IN2O4S
Canonical SMILES CC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)F)NC(=O)C2=C(C(=CC=C2)I)C(=O)NC(C)(C)CS(=O)(=O)C
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) ZGNITFSDLCMLGI-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C23H22F7IN2O4S/c1-12-10-13(21(24,22(25,26)27)23(28,29)30)8-9-16(12)32-18(34)14-6-5-7-15(31)17(14)19(35)33-20(2,3)11-38(4,36)37/h5-10H,11H2,1-4H3,(H,32,34)(H,33,35)/f/h32-33H
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 Benzene-dicarboxamide
Minimum active substance purity 960
Known relevant impurities -
Substance origin Synthetic
Mode of action Exhibits larvicidal activity as an orally ingested toxicant by targeting and disrupting the Ca2+ balance
CAS RN 272451-65-7
EC number -
CIPAC number 788
US EPA chemical code 027602
PubChem CID 11193251
Molecular mass (g mol-1) 682.39
PIN (Preferred Identification Name) N1-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-3-iodo-N2-[1-(methanesulfonyl)-2-methylpropan-2-yl]benzene-1,2-dicarboxamide
IUPAC name 3-iodo-N'-(2-mesyl-1,1-dimethylethyl)-N-{4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-o-tolyl}phthalamide
CAS name N2-(1,1-dimethyl-2-(methylsulfonyl)ethyl)-3-iodo-N1-(2-methyl-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl)phenyl)-1,2-benzenedicarboxamide
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) 28
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Colourless, odourless crystalline solid
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
  • Belt
  • Fame
  • Fenos
  • Synapse
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Usually supplied as a suspension concentrate or wettable granules.


ENVIRONMENTAL FATE

for flubendiamide

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) 0.029 R4 Low
Solubility - In organic solvents at 20oC (mg l-1) 488 A5 - p-Xylene -
0.835 A5 - n-heptane -
26000 A5 - methanol -
8120 A5 - 1,2-dichloroethane -
Melting point (oC) 217.5 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 255 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 1.38 X 1004 Calculated -
Log P 4.14 A5 High
Bulk density (g ml-1)/Specific gravity 1.66 R4 -
Dissociation constant (pKa) at 25oC - - -
Note:
Vapour pressure at 20oC (mPa) 0.1 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) - - -
GUS leaching potential index Click here for a note on the limitations of the GUS index 3.98 Calculated High 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 1.33 X 10+00 Calculated -
Note -
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 soln: 204.4nm=39066
Acidic soln: 203nm=40500
Basic soln: 218nm=24967
- -
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) 500 A5 Very persistent
DT50 (lab at 20oC) 500 A5 Very persistent
DT50 (field) - - -
DT90 (lab at 20oC) - - -
DT90 (field) - - -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 >365days
Dissipation rate RL50 on plant matrix Value 2.9 R4 -
Note Published literature RL50 range 0.7-6.1 days, 4 crops field & undercover, various matrices, n=7
Dissipation rate RL50 on and in plant matrix Value 2.9 R4 -
Note Published literature RL50 range 1.0-5.0 days, 4 field grown crops field, various matrices, n=8
Aqueous photolysis DT50 (days) at pH 7 Value 32.5 A5 Stable
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note -
Water-sediment DT50 (days) 500 A5 Stable
Water phase only DT50 (days) 6.9 A5 Moderately 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 - Q3 Slightly mobile
Koc 2197
Notes and range Literature values range 1076-3318 mL/g
Freundlich Kf 22.7 A5 Moderately mobile
Kfoc 334
1/n 0.095
Notes and range EU dossier Kf range 17.2-30.0 mL/g, Kfoc range 1076-3318 mL/g, 1/n range 0.965-1.022, Soils=5
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-(4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl)-3-hydroxy-N-(2-methyl-1-(methylsulfonyl)propan-2-yl)phthalamide This metabolite may cause environmental pollution, click here for further information Soil   0.176   Major fraction; Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-3-hydroxy-N-[2-methyl-1-(methylsulfonyl)propan-2-yl]phthalamide
(Ref: NNI-0001-3-OH)
A-2 - - -
N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl]-3-hydroxy-N-[2-methyl-1-(methylsulfonyl)propan-2-yl]phthalamide
(Ref: NNI-0001-3-OH-hydroxyperfluoroalkyl)
A-10 - - -
5-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-[(3-iodo-2-{[2-methyl-1-(methylsulfonyl)propan-2-yl]carbamoyl}benzoyl)amino]benzoic acid
(Ref: NNI-0001-benzoic acid)
A-18 - - -
N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(hydroxymethyl)phenyl]-3-iodo-N-[2-methyl-1-(methylsulfonyl)propan2-yl]phthalamide
(Ref: NNI-0001-benzylalcohol)
A-16 - - -
2-[2-methyl-1-(methylsulfonyl)propan-2-yl]-1Hisoindole-1,3(2H)-dione
(Ref: NNI-0001-des-iodoalkylphthalimide)
A-27 - - -
2-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-4-iodo-1Hisoindole-1,3(2H)-dione
(Ref: NNI-0001-iodophthalimide)
A-14 - - -
{[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]amino}(oxo)acetic acid
(Ref: NNI-0001-oxalinic acid)
A-31 - - -


ECOTOXICOLOGY

for flubendiamide

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) 73 A5 Whole fish Low potential
CT50 (days) 4.7 -
Mammals - Acute oral LD50 (mg kg-1) >= 2000 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) 18 R4 Rat High
(ppm diet) 200 -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.06 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.060 R4 Pimephales promelas Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.06 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.033 R4 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) > 0.028 A5 Americamysis bahia High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) 1.188 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 0.035 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) 0.0546 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.069 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) > 200 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 500 A5 Eisenia foetida corr Low
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 675 A5 Typhlodromus pyri -
% Effect - - -
Other arthropod (2) LR50 g ha-1 675 A5 Aphidius rhopalosiphi -
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
R4
Dose: 2.24 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 0.053 R4 Outdoor pond life -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for flubendiamide

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 Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 0.069 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.017 A5 Rat, 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) 0.006 A5 Dog, SF=100 -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public No anticipated risks
Occupational No anticipated risks
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 Possible liver, thyroid & kidney toxicant

: 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 IMDG Transport code
Not explosive or oxidising
CLP classification 2013 None allocated at this time
EC Risk Classification Click here to view information omn the EU risk phrases Reproduction risk category 3: R64
N - Dangerous for the environment: R50/53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S13, S36, S57, S46
WHO Classification III - Slightly hazardous
US EPA Classification (formulation) - -
UN Number 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for flubendiamide

Language Name
English flubendiamide
French -
German -
Danish -
Italian -
Spanish -
Greek -
Slovenian -
Polish flubendiamid
Swedish -
Hungarian -
Dutch -

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