Amisulbrom

Amisulbrom	Last updated: 24/12/2020
(Not known by any other names)

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

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/06/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

30/06/2024

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
✓		✓	✓	✓	✓	✓

Also used in

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

2D 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⁻¹

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

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)

Examples of recorded resistance

Physical state

Pale yellow crystalline solid

Formulations

Property

Value

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

Shinkon
Leimay

Example products using this active

Nissan

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)

Not expected to self ignite; Not highly flammable

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

2.51 X 10⁰⁴

Calculated

Log P

4.4

High

Bulk 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

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 on plant matrix

Value

3.9

Note

Cabbage leaves, n=1

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

284

Notes and range

Estimated

Freundlich

K_f

246

Non-mobile

K_foc

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

High

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

176

Threshold for concern

CT₅₀ (days)

0.40

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

Colinius virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0515

Oncorhychus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.037

Pimephales promelas 28 day growth

Moderate

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

0.037

Daphnia magna

High

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

0.0197

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

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

Pseudokirchneriella subcapitata

Moderate

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)

> 100

Low

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

> 100

Low

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)

> 87.5

Eisenia foetida corr

Moderate

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

1000

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

1000

>
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 1.6mg kg⁻¹ 28 days

Mesocosm study data

NOEAEC mg l⁻¹

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)

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H319, H351
Environment: H400, H410

EC Risk Classification

Reproduction risk cat 3: R61
Xn - Harmful: R62, Xi - Irritant: R41
N - Dangerous for the environment; R50/53

EC Safety Classification

S35, S57

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

amisulbrom

French

German

Danish

Italian

Spanish

Greek

Polish

amisulbrom

Swedish

amisulbrom

Hungarian

Dutch

Record last updated:	24/12/2020
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