| amisulbrom |
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SUMMARY
A sulfonamide fungicide that is approved for use in the EU. It has a low aqueous solubility, is slightly volatile with a calulated moderate mobility. There is not a high risk of the substance leaching to groundwater. It may be persistent in soil systems but is not expected to persist in water systems. It has a low mammalian toxicity but it is considered to be a reproduction toxicant. It is moderately toxic to birds and honey bees but poses a greater risk to aquatic species and earthworms. GENERAL INFORMATION 
for amisulbrom
Description: A new sulfonamide fungicide for use on potatoes and other crops
Example pests controlled: Late blight (Phytophthora infestans); Downy mildew (Plasmopara viticola)' Fruit rot (Phytophthora capsici)
Example applications: Potatoes; Tomatoes; Grapes; Curcubits; Bell peppers
Efficacy & activity: -
Availability status: Current
Introduction & key dates: -
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | UK |
| Date inclusion expires | 30/06/2024 |
| 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 | C13H13BrFN5O4S2 |
| Canonical SMILES | CC1=C(C2=C(N1S(=O)(=O)C3=NN(C=N3)S(=O)(=O)N(C)C)C=C(C=C2)F)Br |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | BREATYVWRHIPIY-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C13H13BrFN5O4S2/c1-8-12(14)10-5-4-9(15)6-11(10)20(8)25(21,22)13-16-7-19(17-13)26(23,24)18(2)3/h4-7H,1-3H3 |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide | |||
| Substance group | Sulfonamide | |||
| Minimum active substance purity | 985 g/Kg | |||
| Known relevant impurities | EU dossier - 3-bromo-6-fluoro-2-methyl-1-(1H-1,2,4-triazole-3-ylsulfonyl)indole (metabolite IT-4) < 2 g/kg | |||
| Substance origin | Synthetic | |||
| Mode of action | Qil (Quinone Inside Inhibitor) action. Respiration inhibitor. | |||
| CAS RN | 348635-87-0 | |||
| EC number | - | |||
| CIPAC number | 789 | |||
| US EPA chemical code | - | |||
| PubChem CID | 10238657 | |||
| Molecular mass (g mol-1) | 466.31 | |||
| PIN (Preferred Identification Name) | 3-(3-bromo-6-fluoro-2-methyl-1H-indole-1-sulfonyl)-N,N-dimethyl-1H-1,2,4-triazole-1-sulfonamide | |||
| IUPAC name | 3-(3-bromo-6-fluoro-2-methylindol-1-ylsulfonyl)-N,N-dimethyl-1,2,4-triazole-1-sulfonamide | |||
| CAS name | 3-((3-bromo-6-fluoro-2-methyl-1H-indol-1-yl)sulfonyl)-N,N-dimethyl-1H-1,2,4-triazole-1-sulfonamide | |||
| Other status information | PAN listed Highly Hazardous Chemical | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | 21 | |||
| Examples of recorded resistance | - | |||
| Physical state | Pale yellow 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 | Buffer probably required in UK - see product label | |||
| Formulation and application details | Usually supplied as a suspension concentrate that is mixed with water and used as a spray. No UK approval for aerial use. | |||
ENVIRONMENTAL FATE
for amisulbrom
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.11 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 264 | A5 - Hexane | - | |
| 88600 | A5 - Toluene | - | ||
| 10100 | A5 - Methanol | - | ||
| 2600 | A5 - Octanol | - | ||
| Melting point (oC) | 128.6 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 242 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.51 X 1004 | Calculated | - |
| Log P | 4.4 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.85 | Q2 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 1.8 X 10-05 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.8 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
-0.49 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 5.35 X 10-03 | Calculated | - |
| Note | Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral sol.: 254nm=11300 Acid soln.: 254nm=11500 Basic soln.: 222nm = 26300, 265nm=6520 |
A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 143 | A5 | Persistent |
| DT50 (lab at 20oC) | 143 | A5 | Persistent | |
| DT50 (field) | 8.6 | A5 | Non-persistent | |
| DT90 (lab at 20oC) | 1011 | A5 | - | |
| DT90 (field) | 30.6 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 48.4-937.9 days, DT90 range 161-1942 days; Field studies DT50 range 4.3-12.6, DT90 range 14.2-41.9 dats | |||
| Dissipation rate RL50 on plant matrix | Value | 3.9 | R3 | - |
| Note | Cabbage leaves, n=1 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 5.5 | R4 | - |
| Note | Published literature RL50 range 3.0-7.9 days, cucumber & melon fruits, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 0.8 | A5 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 87.1 | A5 | Moderately persistent |
| Note | pH dependent: 106.1 days @ pH4; 7.0day @ pH9 | |||
| Water-sediment DT50 (days) | 100.1 | A5 | Slow | |
| Water phase only DT50 (days) | 6.7 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | Q2 | Moderately mobile |
| Koc | 284 | |||
| Notes and range | Estimated | |||
| Freundlich | Kf | 246 | A5 | Non-mobile |
| Kfoc | 16965 | |||
| 1/n | 0.94 | |||
| Notes and range | EU dossier Kf range 147-378 mL/g, Kfoc range 8156-44231 mL/g, 1/n range 0.9-1.0, Soils=6 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 3-bromo-6-fluoro-2-methyl-1-(1H-1,2,4-triazole-3-ylsulfonyl)indole |
Soil | 0.337 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 3-(3-bromo-6-fluoro-2-hydroxymethylindol-1-ylsulfonyl)-N,N-dimethyl-1,2,4-triazole-1-sulfonamide | IT-2 | Humans | - | - |
| 3-(3-bromo-6-fluoro-5-hydroxymethy-2-hydroxymethylindol-1-ylsulfony)-N,N-dimethyl-1,2,4-triazole-1-sulfonamide | IT-3 | Plants | - | - |
| 3-(3-bromo-6-fluoro-5-hydroxymethy-1-(1H-1,2,4-triazole-2-ylsulfony)indole | IT-5 | Plants | - | - |
| 3-(3-bromo-6-fluoro-5-hydroxymethy-2-hydroxymethyl-1-(1H-1,2,4-triazole-3-ylsulfony)indole | IT-6 | Plants | - | - |
| 2-((1-N,N-dimethylaminosulfonyl-1,2,4-triazole-3-yl)sulfonylamino)-4-fluorobenzoic acid | IT-9 | Animal | - | - |
| 2-((1H-1,2,4-triazole-3-yl)sulfonylamino)-4-fluorobenzic acid | IT-10 | - | - | - |
| 3-(6-fluoro-2-hydroxy-2-methyl-3-oxoindolin-1-ylsulfonyl)-N,N,dimethyl-1,2,4-triazole-1-sulfonamide | IT-11 | - | - | - |
| 3-(1H,1,2,4-triazole-3-ylsulfonyl)-6-fluoro-2-methylindole | IT-12 | - | - | - |
| 3-bromo-6-fluoro-2-methyl-1-(1-methyl-1,2,4-triazole-3-ylsulfonyl)indole | IT-15 | Surface water; Sediments | - | - |
| 2-acetylamino-4-fluorobenzoic acid | I-2 | Surface water | - | - |
| 2-acetylamino-4-fluoro-hydroxybenzoic acid | I-8 (hydroxylated I-2) | Surface water | - | - |
| 2,2-oxybis)6-fluoro-2-methylindolin-3-one) | I-9 (I-5 dimer) | - | - | - |
| 1-(N,N-dimethylaminosulfonyl)-1,2,4-triazole-3-sulfonic-acid | T-1 | Surface water | - | - |
| 1-(N,N-dimethylaminosulfonyl)-1,2,4-triazole | T-2 | - | - | - |
| 1H-1,2,4-triazole-3-sulfonic acid | T-3 | Surface water | - | - |
| 1H-1,2,4-triazole | T-4 | Surface water | - | - |
| 2-amino-3-(1H-1,2,4-triazol-1-yl)propanoic acid | T-5 | - | - | - |
| 2-(1H-1,2,4-triazol-1-yl)acetic acid | T-6 | - | - | - |
| 5-(N,N-dimethylaminosulfonyl)-1H-1H-1,2,4-triazole | T-7 (T-2 isomer) | Surface water | - | - |
| 3-bromo-6-fluoro-2-methylindole | I-1 | - | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 176 | A5 | Threshold for concern |
| CT50 (days) | 0.40 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 1080.5 mg kg bw-1 day-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.0515 | A5 Oncorhychus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.037 | A5 Pimephales promelas, 28-day growth | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.037 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.0197 | 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) | 0.1114 | 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) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.20 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| 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) | > 87.5 | A5 Eisenia foetida, corr | Moderate | |
| 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 | 1000 | > A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 1000 | > A5 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.6mg kg-1, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for amisulbrom
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) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 2.85 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.1 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.3 | 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) | 0.15 | A5 Rabbit, SF=100 | - | |
| Dermal penetration studies (%) | 0.6-12 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Acceptable for proposed uses | ||
| Occupational | Acceptable for proposed 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 toxicant May cause eye damage |
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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 |
|
| General |
Not explosive or oxidising | |||
| CLP classification 2013 | Health: H319, H351 Environment: H400, H410 |
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| EC Risk Classification |
Reproduction risk cat 3: R61 Xn - Harmful: R62, Xi - Irritant: R41 N - Dangerous for the environment; R50/53 |
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| EC Safety Classification |
S35, S57 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | - | - | ||
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | amisulbrom |
| French | - |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | - |
| Greek | - |
| Slovenian | - |
| Polish | amisulbrom |
| Swedish | amisulbrom |
| Hungarian | - |
| Dutch | - |
Record last updated: Friday 14 September 2018
Contact: aeru@herts.ac.uk