| flumiclorac-pentyl (Ref: S 23031) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
SUMMARY
Flumiclorac-pentyl is a herbicide without EU regulatory approval for use. It has a low aqueous solubility, is volatile and, based on its chemical properties, whilst it is mobile it is not expected to leach to groundwater. It tends not to be persistent in soil and aquatic systems degrading by both hydrolysis and photolysis. It has a low mammalian toxicity and is a recognised irritant. It is moderately toxic to fish and aquatic invertebrates, and relatively non-toxic to honey bees. GENERAL INFORMATION 
for flumiclorac-pentyl
Description: A post-emergence herbicide used to control problematic broad-leaved weeds
Example pests controlled: Borad-leaved weeds including Xanthium strumarium and Ambrosia artemisiifolia
Example applications: Corn; Soybean; Cotton
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1995, USA
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Not applicable |
| Date inclusion expires | Not applicable |
| EU Candidate for substitution (CfS) | - |
| 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 | C21H23ClFNO5 |
| Canonical SMILES | CCCCCOC(=O)COC1=C(C=C(C(=C1)N2C(=O)C3=C(C2=O)CCCC3)F)Cl |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | IRECWLYBCAZIJM-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C21H23ClFNO5/c1-2-3-6-9-28-19(25)12-29-18-11-17(16(23)10-15(18)22)24-20(26)13-7-4-5-8-14(13)21(24)27/h10-11H,2-9,12H2,1H3 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |||
| Substance group | Dicarboximide | |||
| Minimum active substance purity | 950 g/kg | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Fast contact action, absorbed by foliage. Cell membrane disruption - enzyme protoporphyrinogen oxidase inhibitor. | |||
| CAS RN | 87546-18-7 | |||
| EC number | - | |||
| CIPAC number | - | |||
| US EPA chemical code | 128724 | |||
| PubChem CID | 443048 | |||
| Molecular mass (g mol-1) | 423.86 | |||
| PIN (Preferred Identification Name) | pentyl [2-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-4-fluorophenoxy]acetate | |||
| IUPAC name | pentyl [2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)-4-fluororophenoxy]acetate | |||
| CAS name | pentyl [2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetate | |||
| 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 | Euphorbia heterophylla | |||
| Physical state | Beige coloured 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 | - | |||
ENVIRONMENTAL FATE
for flumiclorac-pentyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.189 | L3 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 47800 | L3 - Methanol | - | |
| 3280 | L3 - Hexane | - | ||
| 16000 | L3 - n-Octanol | - | ||
| 590000 | L3 - Acetone | - | ||
| Melting point (oC) | 89 | L3 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | 68 | L3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 9.77 X 1004 | Calculated | - |
| Log P | 4.99 | L3 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.33 | L3 | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 0.01 | L3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | - | - | - | |
GUS leaching potential index  |
1.00 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 2.25 X 10-03 | 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) | 2.5 | L3 | Non-persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | 10 | F3 | Non-persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | General literature DT50 studies range 0.45-4.5 days; Other sources: 10 days (US3, DW4) | |||
| 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 | 0.8 | L3 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 0.8 | L3 | Non-persistent |
| Note | pH sensitive: DT50 4.2 days at pH 5, 6 minutes at 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 | - | US3 | Mobile |
| Koc | 30 | |||
| Notes and range | - | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 5-amino-2-chloro-4-fluorophenoxyacetic acid | - | Soil (Aerobic) | - | - |
| N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide | - | Water (Anaerobic) | - | - |
| N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalamic acid | - | Water (Anaerobic) | - | - |
| pentyl 5-amino-2-chloro-4-fluorophenoxyacetate | - | Water (Anaerobic) | - | - |
| 3,4,5,6-tetrahydrophthalic acid | - | Soil (Aerobic) | - | - |
| 1-hydroxy-trans-1,2-cyclohexane-dicarboxylic acid | - | Soil (Aerobic) | - | - |
| pentyl 2-chloro-4-fluoro-5[2-carboxycyclohexenylcarboxamido]phenoxyacetate | - | Soil (Aerobic) | - | - |
| 3,4,5,6-tetrahydrophthalic acid | - | Soil (Photolysis) | - | - |
| 2-chloro-4-fluoro-5-(3,4,5,6-tetra-hydrophthalimino)phenoxyacetic acid | - | Soil (Photolysis) | - | - |
ECOTOXICOLOGY
for flumiclorac-pentyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | - | - | - |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | L3 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2250 | L3 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 1.1 | L3 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 38.0 | L3 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.46 | F3 Americamysis bahia | Moderate | |
| 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) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | - | - | - | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 196 | L3 | Low |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Bumblebees (Bombus spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| - | ||||
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| - | ||||
| Mason bees (Osmia spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Other pollinators (1) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Other pollinators (2) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Earthworms - Acute 14 day LC50 (mg kg-1) | - | - | - | |
| 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 | - | - | - |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for flumiclorac-pentyl
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 | L3 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | L3 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 5.51 | L3 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | - | - | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | - | - | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | - | - | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
|
A0; B0; C0; D0; E0 | - |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | No further information available | |||||||
| Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other : Yes, known to cause a problem  : No, known not to cause a problem  : Possibly, status not identified - : No data found |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
No information available | |||
| CLP classification 2013 | - | |||
| EC Risk Classification |
Xn - Harmful: R43, R65 Xi - Irritant: R36/38 N - Dangerous for the environment: R50/53 |
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| EC Safety Classification |
S5, S23 | |||
| WHO Classification | NL | - | Not listed | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
TRANSLATIONS
for flumiclorac-pentyl
| Language | Name |
| English | flumiclorac-pentyl |
| French | - |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | flumiclorac pentil |
| Greek | - |
| Slovenian | - |
| Polish | flumiklorak pentylowy |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Thursday 31 May 2018
Contact: aeru@herts.ac.uk