| sulfentrazone (Ref: FMC 97285) |
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SUMMARY
Sulfentrazone is a herbicide without EU regulatory approval for use. It has a high aqueous solubility, is volatile and, based on its chemical properties, is mobile with a high potential to leach to groundwater. It can be very persistent in soil and aquatic systems. It is not susceptible to hydrolysis but may degrade via photolysis in aquatic systems. It has a relatively low mammalian toxicity but may bioaccumulate. Whilst its toxicity to birds is relatively low there is greater risk to aquatic species and honey bees. GENERAL INFORMATION 
for sulfentrazone
Description: A herbicide for control of broad-leaved weed and some grasses
Example pests controlled: Carpetweed; Crabgrass; Daisy; Dock; Lambsquarter; Morning glory; Pigweed; Thistles; Waterhemp
Example applications: Soybeans; Chickpeas; Tobacco; Sugarcane; Non-agricultrual areas including highways, roads, fence rows, storage areas, industrial sites
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1991
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: USA
Chemical structure:
| Isomerism | - |
| Chemical formula | C11H10Cl2F2N4O3S |
| Canonical SMILES | CC1=NN(C(=O)N1C(F)F)C2=CC(=C(C=C2Cl)Cl)NS(=O)(=O)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | OORLZFUTLGXMEF-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C11H10Cl2F2N4O3S/c1-5-16-19(11(20)18(5)10(14)15)9-4-8(17-23(2,21)22)6(12)3-7(9)13/h3-4,10,17H,1-2H3 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |
| Substance group | Aryl triazolinone | |
| Minimum active substance purity | >92.55% | |
| Known relevant impurities | - | |
| Substance origin | Synthetic | |
| Mode of action | Absorbed by roots and foliage and translocated. Cell membrane disruption - PPO inhibitor. | |
| CAS RN | 122836-35-5 | |
| EC number | - | |
| CIPAC number | None allocated | |
| US EPA chemical code | 129081 | |
| PubChem CID | 86369 | |
| Molecular mass (g mol-1) | 387.19 | |
| PIN (Preferred Identification Name) | N-{2,4-dichloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]phenyl}methanesulfonamide | |
| IUPAC name | 2',4'-dichloro-5'-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)methanesulfonanilide | |
| CAS name | N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide | |
| Other status information | Possible groundwater contaminant | |
| 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 | Light tan coloured solid forumated as an off-white liquid with faint odour | |
| 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 | Available in a variety of formulations including flowable liquid end-use products and water dispersible granules. | |||
ENVIRONMENTAL FATE
for sulfentrazone
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 780 | F4 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 640000 | P4 - Acetone | - | |
| 186000 | P4 - Acetonitrile | - | ||
| 66600 | P4 - Toluene | - | ||
| 110 | P4 - Hexane | - | ||
| Melting point (oC) | 122 | F4 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 9.79 X 1000 | Calculated | - |
| Log P | 0.991 | F4 | Low | |
| Bulk density (g ml-1)/Specific gravity | 0.53 | F4 | - | |
| Dissociation constant (pKa) at 25oC | 6.56 | F4 | - | |
| Note: Weak acid | ||||
| Vapour pressure at 20oC (mPa) | 1.30 X 10-04 | L3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | - | - | - | |
GUS leaching potential index  |
6.16 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 2.41 X 10+01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | Max @ 110nm | P4 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 541 | F4 | Very persistent |
| DT50 (lab at 20oC) | 400 | F3 | Very persistent | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Other sources: DT50 circa 18 months (L3); Other literature 121-302 days (Q3) | |||
| 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 | Stable | F4 | - |
| Note | Unstable in UV light | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | L3 | - |
| Note | Stable under normal environmental conditions | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | F3 | Mobile |
| Koc | 43 | |||
| Notes and range | Other sources: 104 mL/g (US3, DW3) | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
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| 3-hydroxymethyl sulfentrazone (N-(2,4-dichloro-5-(4-(difluoromethyl)-yl)pheny)methanesulfonamide | Soil | - | - | |
ECOTOXICOLOGY
for sulfentrazone
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | Low risk | F4 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 2855 | F4 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 10 | L3 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2250 | F4 Anas platyrhynchos | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 93.8 | F4 Lepomis macrochirus | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 2.95 | P3 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 60.4 | F4 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.2 | P3 Daphnia magna, survival | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.800 | 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) | 0.29 | F4 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 32.8 | F4 Anabaena flos-aqua | Low | |
| 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) | > 25.1 | F4 | Moderate |
| 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 NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms | Acute LC50 (mg kg-1) | - | - | - | Chronic NOEC (mg kg-1) | - | - | - |
| 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 sulfentrazone
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) | > 2855 | F4 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | F4 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 4.13 | F4 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 | |||
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A0; B0; C0; D0; E3 | - |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Moderately toxic through the oral route, less so via dermal exposure Possible liver and kideny toxicant |
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| 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 |
Thermal decomposition and burning may form toxic by-products Slightly combustible |
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| CLP classification 2013 | Health: H332, H373 Environment: H411 |
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| EC Risk Classification |
Not classified: Obsolete | |||
| EC Safety Classification |
Not classified: Obsolete | |||
| WHO Classification | NL | - | Not listed | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
TRANSLATIONS
for sulfentrazone
| Language | Name |
| English | sulfentrazone |
| French | sulfentrazone |
| German | Sulfentrazon |
| Danish | sulfentrazon |
| Italian | sulfentrazone |
| Spanish | sulfentrazona |
| Greek | - |
| Slovenian | sulfentrazon |
| Polish | sulfentrazon |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Wednesday 27 November 2019
Contact: aeru@herts.ac.uk