| flubendiamide (Ref: NNI-0001) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL 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: 
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 |
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Chemical structure:
| 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 |
| 2D structure diagram/image available? | Yes |
General status:
| 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 |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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  |
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 |
Value | 1.33 X 10+00 | Calculated | - |
| Note | - | |||
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
|
| 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 |
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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (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 | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
IMDG Transport code Not explosive or oxidising |
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| CLP classification 2013 | None allocated at this time | |||
| EC Risk Classification |
Reproduction risk category 3: R64 N - Dangerous for the environment: R50/53 |
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| EC Safety Classification |
S2, S13, S36, S57, S46 | |||
| WHO Classification | III | - | Slightly hazardous | |
| US EPA Classification (formulation) | - | - | ||
| UN Number | 3082 | |||
| Waste disposal & packaging |
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