| beflubutamid (Ref: UBH 820) |
 |
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SUMMARY
Beflubutamid is a selective herbicide used to control broad-leaved weeds in cereals. It has a low aqueous solubility and is quite volatile. There is a low risk of groundwater contamination and it is non-persistent in soil. However it can be quite persistent in water bodies. It has a moderate oral toxicity to mammals and has been shown to cause reproduction or development issues in humans. It is moderately toxic to birds, earthworms and most aquatic organisms. It has a low toxicity to honeybees. GENERAL INFORMATION 
for beflubutamid
Description: An amide herbicide for pre- and early post-emergence control of broad-leaved weeds
Example pests controlled: Chickweed; Loose silky bent; Field pansy; Scented mayweed; Wild pansy; Field speedwell; Ivy-leaved speedwell; Groundsel
Example applications: Cereals including wheat, barley, rye, triticale
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1998, USA
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Germany/Lithuania |
| Date inclusion expires | 31/07/2019 |
| 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 | A chiral molecule. The racemate mixture is normally comprised of equimolar amounts of R- and S-beflubutamid. |
| Chemical formula | C18H17F4NO2 |
| Canonical SMILES | CCC(C(=O)NCC1=CC=CC=C1)OC2=CC(=C(C=C2)F)C(F)(F)F |
| Isomeric SMILES | CC[C@H](Oc1ccc(F)c(c1)C(F)(F)F)C(=O)NCc2ccccc2 |
| International Chemical Identifier key (InChIKey) | FFQPZWRNXKPNPX-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C18H17F4NO2/c1-2-16(17(24)23-11-12-6-4-3-5-7-12)25-13-8-9-15(19)14(10-13)18(20,21)22/h3-10,16H,2,11H2,1H3,(H,23,24) |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |
| Substance group | Amide | |
| Minimum active substance purity | 970 G/Kg | |
| Known relevant impurities | EU dossier - none declared | |
| Substance origin | Synthetic | |
| Mode of action | Bleaching: inhibition of carotenoid biosynthesis. | |
| CAS RN | 113614-08-7 | |
| EC number | - | |
| CIPAC number | 662 | |
| US EPA chemical code | - | |
| PubChem CID | 6451159 | |
| Molecular mass (g mol-1) | 355.12 | |
| PIN (Preferred Identification Name) | rac-(2R)-N-benzyl-2-[4-fluoro-3-(trifluoromethyl)phenoxy]butanamide | |
| IUPAC name | (RS)-N-benzyl-2-(α,α,α,4-tetrafluoro-m-tolyloxy)butyramide | |
| CAS name | 2-[4-fluoro-3-(trifluoromethyl)phenoxy]-N-(phenylmethyl)butanamide | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | F1 | |
| Herbicide Resistance Classification (WSSA) | 12 | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | - | |
| Physical state | White fluffy powder | |
| Related substances & organisms | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically | - | |||
| 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 | - | |||
ENVIRONMENTAL FATE
for beflubutamid
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 3.29 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 600000 | A5 - Acetone | - | |
| 571000 | A5 - Ethyl acetate | - | ||
| 473000 | A5 - Methanol | - | ||
| 2180 | A5 - n-Heptane | - | ||
| Melting point (oC) | 75 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 128 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.91 X 1004 | Calculated | - |
| Log P | 4.28 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.33 | A5 | - | |
| Dissociation constant (pKa) at 25oC | N/a | A3 | - | |
| Note: Unlikely to dissociate | ||||
| Vapour pressure at 20oC (mPa) | 1.10 X 10-02 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.10 X 10-04 | A5 | Non-volatile | |
GUS leaching potential index  |
1.37 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 3.15 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 29.6 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 29.6 | A5 | Non-persistent | |
| DT50 (field) | 55 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | 197 | A5 | - | |
| DT90 (field) | 182 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 5-118 days, DT90 range 16-365 days, field studies DT50 range 15-103 days, DT90 range 49-343 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | - | - | - |
| Note | - | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 48 | A5 | Stable |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable at pH 5 to pH 9 for up to 5 days | |||
| Water-sediment DT50 (days) | 57 | A5 | Moderately fast | |
| Water phase only DT50 (days) | 18 | A5 | Slow | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 23.6 | A5 | Slightly mobile |
| Kfoc | 1171 | |||
| 1/n | 0.908 | |||
| Notes and range | EU dossier Kf 8.5-43.0 mL/g, Kfoc range 496-1793 mL/g, 1/n 0.86-0.93, Soils=3 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| phenoxybutyric acid (Ref: UR-50604) |
Soil | 0.261 | Major fraction, Relevant | |
ECOTOXICOLOGY
for beflubutamid
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 230 | A5 | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 29 | L3 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5200 ppm | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 1.86 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.11 | A5 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 1.64 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.005 | 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) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | 0.02 | A5 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 69.2 | A5 Selenastrum capricornutum | Low | |
| 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) | 366 | A5 corr | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | < 0.17 | A5 Eisenia foetida, orr | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 8.0 | Mortality A5 Typhlodromus pyri |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 0 | Mortality A5 Aphidius rhopalosiphi |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.6 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for beflubutamid
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) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 5.0 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.02 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A5 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.3 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 100 | A3 default | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Risks acceptable for intended uses | ||
| Occupational | Risks acceptable for intended uses | |||
| 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, kidney and thyroid 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 | |||
| CLP classification 2013 | Environment: H400, H410 | |||
| EC Risk Classification |
N - Dangerous for the environment: R50/53 | |||
| EC Safety Classification |
S60, S61 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | beflubutamid |
| French | beflubutamide |
| German | Beflubutamid |
| Danish | beflubutamid |
| Italian | beflubutamid |
| Spanish | beflubutamid |
| Greek | - |
| Slovenian | beflubutamid |
| Polish | beflubutamid |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk