| oxyfluorfen (Ref: RH 2915) |
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GENERAL INFORMATION 
for oxyfluorfen
Description: A broad-spectrum, pre- and post-emergent herbicide used to control certain annual weeds in vegetables, fruit and other crops
Example pests controlled: Annual broad-leaved; Grassy weeds
Example applications: Sugarcane; Vegetables including alliums, peas, cabbage; Fruit; Nuts including almonds; Cotton; Ornamentals; non-crop areas including landscapes, residential and amenity sites
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1975, first reported; 1976, first marketed
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Spain/Hungary |
| Date inclusion expires | 31/12/2021 |
| EU Candidate for substitution (CfS) | Yes - two 'Persistent-Bioaccumulative-Toxic' criteria |
| 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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Also used in: Australia, USA
Chemical structure:
| Isomerism | - |
| Chemical formula | C15H11ClF3NO4 |
| Canonical SMILES | CCOC1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(F)F)Cl)[N+](=O)[O-] |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | OQMBBFQZGJFLBU-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C15H11ClF3NO4/c1-2-23-14-8-10(4-5-12(14)20(21)22)24-13-6-3-9(7-11(13)16)15(17,18)19/h3-8H,2H2,1H3 |
| 2D structure diagram/image available? | Yes |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Oxyfluorfen | - |  |
General status:
| Pesticide type | Herbicide | |
| Substance group | Diphenyl ether | |
| Minimum active substance purity | 970 g/kg | |
| Known relevant impurities | EU dossier - N,N-domethylnitrosamine 0.01g/kg | |
| Substance origin | Synthetic | |
| Mode of action | Selective with contact action. Inhibits protoporphyrinogen oxidase, leading to irreversible cell membrane damage. | |
| CAS RN | 42874-03-3 | |
| EC number | 255-983-0 | |
| CIPAC number | 538 | |
| US EPA chemical code | 111601 | |
| PubChem CID | 39327 | |
| Molecular mass (g mol-1) | 361.7 | |
| PIN (Preferred Identification Name) | - | |
| IUPAC name | 2-chloro-α,α,α-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl ether | |
| CAS name | 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | E | |
| Herbicide Resistance Classification (WSSA) | 14 | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | - | |
| Physical state | Orange to brown crystalline powder | |
| 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 granules or an emulsifiable concentrate. | |||
ENVIRONMENTAL FATE
for oxyfluorfen
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.116 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 134000 | A5 - Acetone | - | |
| 3800 | A5 - n-Heptane | - | ||
| 30000 | A5 - Methanol | - | ||
| 132000 | A5 - Ethyl acetate | - | ||
| Melting point (oC) | 85.3 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 331 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 7.24 X 1004 | Calculated | - |
| Log P | 4.86 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.53 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.026 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 0.02382 | A5 | Non-volatile | |
GUS leaching potential index  |
0.26 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 7.35 X 10-03 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral solution: 275nm = 6135, 320nm = 4730; [Acidic solution: 273nm = 6276, 320nm = 4730; [Basic solution: 273nm = 6445, 320nm = 4828 | A5 | - | |
| Surface tension (mN m-1) | 72.19 | A5 at 19oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 35 | G3 | Moderately persistent |
| DT50 (lab at 20oC) | 138 | A5 | Persistent | |
| DT50 (field) | 73 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | 663 | A5 | - | |
| DT90 (field) | 417 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier Lab studies DT50 range 62-438 days; DT90 range 231-1771 days, Field data DT50 range 31-172 days, DT90 range 274-571 days; Other literature data DT50 30-60 days | |||
| Dissipation rate RL50 on plant matrix | Value | 1.6 | R3 | - |
| Note | Onion leaves, n=1 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 3.6 | R4 | - |
| Note | Published literature RL50 range 1.0-6.0 days, 2 field crops, various matrices, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 5.6 | A5 | Moderately fast |
| Note | DT50: 4.3 days at 30 deg N, 5.6 days 40 deg N, 8.9 days 50 deg N, 20.5 days 60 deg N, mean seasonal value | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable pH 5 to pH 9 | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 99.37 | A5 | Non-mobile |
| Kfoc | 7566 | |||
| 1/n | 0.92 | |||
| Notes and range | EU dossier Kf range 8.5-228.6, Kfoc range 2891-13711 mL/g, 1/n range 0.787-1.076 | |||
| pH sensitivity | No | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| (Ref: RH-120162) | - | Rat (Faeces) | - | - |
| (Ref: RH-120450) | - | Rat (Faeces) | - | - |
| (Ref: RH-120832) | - | Rat (Faeces) | - | - |
| (Ref: RH-123394) Note: Minor metabolite |
- | Water (Photolysis) | - | - |
| 3-Chloro-4-hydroxy benzoic acid (Ref: RH-31680) |
- | Unknown | - | - |
| (Ref: RH-31689) | - | Soil (Photolysis) | - | - |
| (Ref: RH-34670) | hydro-oxyfluorfen | Rat (Faeces); Water (Photolysis) | - | - |
| 4-trifluoromethyl-2-chlorophenol (Ref: RH-34800) |
- | Rat (Urinary); Water (Photolysis); Soil (Photolysis) | - | - |
| (Ref: RH-35451) Note: Minor metabolite |
- | Water (Photolysis) | - | - |
| (Ref: RH-36329) | - | Soil (Photolysis) | - | - |
| (Ref: RH-45298C) | - | Rat (Urinary) | - | - |
| (Ref: RH-45298-C) | - | Rat (Urinary) | - | - |
| (Ref: RH-45451) | - | Rat (Faeces) | - | - |
| (Ref: RH-45469) Note: Minor metabolite |
- | Water (Photolysis); Rat (Faeces) | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 1637 | A4 | Threshold for concern |
| CT50 (days) | 6 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | G4 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | P4 Rat | - |
| (ppm diet) | > 200 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 947 | A5 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | > 462 mg kg bw-1 day-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.25 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.038 | A5 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.072 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.013 | A5 Daphnia magna | Moderate | |
| 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) | 0.08 | 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) | 0.0014 | A5 Lemna gibba | High | |
| Non-target plants | 14.6 | A5 Pomes, Vines Vegetative vigour, ER50 as g/ha |
- | |
| 13.4 | A5 Pomes, Vines Seedling emergence, ER50 as g/ha |
- | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 2.0 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 2.0 | A5 Pseudokirchneriella subcapitata | Low | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 Eisenia foetida | Low | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 24.09 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | 1.25 | A5 Folsomia candida, NOEC reproduction mg kg-1 | - |
| Other arthropod (1) | LR50 g ha-1 | 1440 | > A5 Typhlodromus pyri, protonymphs |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 1440 | > A5 Pardosa spp. |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.44 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for oxyfluorfen
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 | G4 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 3.71 | A5 Rat (nose only, aerosol) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.003 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.30 | A5 Rabbit, 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) | 0.013 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | No unacceptable risks to bystanders identified | ||
| Occupational | Acceptable risk to operator for intended uses Risks identified for workers re-entering sprayed ruit/wine areas - clsoed re-entry periods must be imposed |
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| 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 | Liver and spleen toxicant USEPA - probable human carcinogen |
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: 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 |
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| General |
Not explosive IMDG Transport Code is usually 3 |
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| CLP classification 2013 | None allocated at this time | |||
| EC Risk Classification |
Carcinogen category 3: R40 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S1/2 | |||
| WHO Classification | U | - | Unlikely to present an acute hazard | |
| US EPA Classification (formulation) | IV | - | Caution - Not acutely toxic | |
| UN Number | Usually 1145 | |||
| Waste disposal & packaging |
Packaging Group II (medium danger) | |||
| Language | Name |
| English | oxyfluorfen |
| French | oxyfluorfene |
| German | Oxyfluorfen |
| Danish | oxyfluorfen |
| Italian | oxifluorfen |
| Spanish | oxifluorfen |
| Greek | - |
| Slovenian | oksifluorfen |
| Polish | oksyfluorfen |
| Swedish | - |
| Hungarian | oxifluorfen |
| Dutch | - |
Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk