Amisulbrom

Amisulbrom	Last updated: 18/07/2024
(Not known by any other names)

SUMMARY

A sulfonamide fungicide that is used to control a range of common infections. It has a low aqueous solubility, is slightly volatile with a calculated 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 honeybees but poses a greater risk to aquatic species and earthworms.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Drainflow: Moderately mobile; Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A 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

2007, first registered USA

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/09/2029

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Greece/Finland

Date EC 1107/2009 inclusion expires

30/09/2024

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓	✓	✓	✓		✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
✓		✓	✓	✓	✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Morroco

Chemical structure

Isomerism

None

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

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Sulfonamide fungicide; Triazole fungicide

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⁻¹

Substance origin

Synthetic

Mode of action

Qil (Quinone Inside Inhibitor) action. Respiration inhibitor.

CAS RN

348635-87-0

EC number

672-776-4

CIPAC number

789

US EPA chemical code

016330

PubChem CID

10238657

CLP index number

616-224-00-2

Molecular mass

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 Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

Pale yellow crystalline solid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Nissan
Syngenta

Example products using this active

Shinkon
Leimay

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

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.11

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

264

Hexane

88600

Toluene

10100

Methanol

2600

Octanol

Melting point (°C)

128.6

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

242

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

2.51 X 10⁰⁴

Calculated

Log P

4.4

High

Fat solubility of residues

Solubility

Likely to be soluble

Data type

Based on chemical group

Density (g ml⁻¹)

1.85

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.8 X 10^-05

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

2.8 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral sol.: 254nm=11300
Acid soln.: 254nm=11500
Basic soln.: 222nm = 26300, 265nm=6520

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

143

Persistent

DT₅₀ (lab at 20 °C)

143

Persistent

DT₅₀ (field)

8.6

Non-persistent

DT₉₀ (lab at 20 °C)

1011

Very persistent

DT₉₀ (field)

30.6

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 (days) on plant matrix

Value

3.9

Note

Cabbage leaves, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.5

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

Fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

87.1

Moderately persistent

Note

pH dependent: 106.1 days at pH4; 7.0day at pH9

Water-sediment DT₅₀ (days)

100.1

Slow

Water phase only DT₅₀ (days)

6.7

Moderately fast

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Moderately mobile

K_oc (mL g⁻¹)

284

Notes and range

Estimated

Freundlich

K_f (mL g⁻¹)

246

Non-mobile

K_foc (mL g⁻¹)

16965

¹/_n

0.94

Notes and range

EU dossier K_f range 147-378 mL g⁻¹, K_foc range 8156-44231 mL g⁻¹, ¹/_n range 0.9-1.0, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.21

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

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

2.3

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

176

Threshold for concern

CT₅₀ (days)

0.40

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3-(6-fluoro-2-hydroxy-2-methyl-3-oxoindolin-1-ylsulfonyl)-N,N,dimethyl-1,2,4-triazole-1-sulfonamide (Ref: IT-11)

Minor fraction

0.037

3-bromo-6-fluoro-2-methyl-1-(1H-1,2,4-triazol-3-ylsulfonyl)-1H-indole

Major fraction

0.337

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

3-bromo-6-fluoro-2-methyl-1-(1H-1,2,4-triazol-3-ylsulfonyl)-1H-indole (Ref: IT-4)

Relevancy unknown

1-(N,N-dimethylaminosulfonyl)-1,2,4-triazole-3-sulfonic-acid (Ref: T-1)

Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-bromo-6-fluoro-2-methyl-1-(1-methyl-1,2,4-triazole-3-ylsulfonyl)indole

IT-15

Surface water; Sediments

3-bromo-6-fluoro-2-methylindole

I-1

Animal

3-(3-bromo-6-fluoro-5-hydroxymethy-2-hydroxymethyl-1-(1H-1,2,4-triazole-3-ylsulfony)indole

IT-6

Plant

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

Plant

2-acetylamino-4-fluorobenzoic acid

I-2

Surface water

2-acetylamino-4-fluoro-hydroxybenzoic acid

I-8 (hydroxylated I-2)

Surface water

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

Plant

3-(3-bromo-6-fluoro-5-hydroxymethy-1-(1H-1,2,4-triazole-2-ylsulfony)indole

IT-5

Plant

2,2-oxybis)6-fluoro-2-methylindolin-3-one)

I-9 (I-5 dimer)

Surface water

1-(N,N-dimethylaminosulfonyl)-1,2,4-triazole-3-sulfonic-acid

T-1

Surface water; Animal

1-(N,N-dimethylaminosulfonyl)-1,2,4-triazole

T-2

Plant

5-(N,N-dimethylaminosulfonyl)-1H-1H-1,2,4-triazole

T-7 (T-2 isomer)

Surface water (photolysis)

1H-1,2,4-triazole-3-sulfonic acid

T-3

Surface water; Plant

1H-1,2,4-triazole

T-4

Surface water; Animal

2-amino-3-(1H-1,2,4-triazol-1-yl)propanoic acid

T-5

Plant; Animal

3-bromo-6-fluoro-2-methyl-1-(1H-1,2,4-triazol-3-ylsulfonyl)-1H-indole

IT-4

Surface water; Sediment

3-(1H,1,2,4-triazole-3-ylsulfonyl)-6-fluoro-2-methylindole

IT-12

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

240

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1080.5 mg kg bw⁻¹ day⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

34.2

Colinus virginianus

Moderate

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 500

Eisenia foetida corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

46.85

Eisenia foetida corr

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 1.6 mg kg⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 1000

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 1000

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0515

Oncorhynchus mykiss

High

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.037

Pimephales promelas 28 day growth

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.037

Daphnia magna

High

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.0197

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

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

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.20

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.85

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.1

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.3

Rabbit SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

Not applicable

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.15

Rabbit SF=100

Dermal penetration studies (%)

0.6-12

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

EU MRL levels for some commodities subject to change in mid-2022

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant
May cause eye damage
CLP data - suspected carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H319, H351
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

amisulbrom

French

German

Danish

Italian

Spanish

Greek

Polish

amisulbrom

Swedish

amisulbrom

Hungarian

Dutch

Norwegian

Record last updated:	18/07/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242