Amidosulfuron

Amidosulfuron	Last updated: 12/01/2021
(Also known as: HOE 075032)

SUMMARY

Amidosulfuron is a broad spectrum herbicide that has approval for use in the EU. It is volatile, highly soluble in water and, based on its chemical properties, has a high potential for leaching to groundwater. It is not persistent in soil systems but may be persistent in water under certain conditions. It has a low mammalian toxicity and would not be expected to bioaccumulate. Amidosulfuron is moderately toxic to most terrestrial and aquatic species.

GENERAL INFORMATION

Description

A post-emergence sulfonylurea herbicide for cleavers and other broad-leaved weed control particularly in cereals

Example pests controlled

Docks; Charlock; Hempweed; Chickweed; Buttercups; Nettles; Mayweed; Shepherd's purse; Forget-me-not; Field pansy

Example applications

Cereals including wheat, barley, oats, triticale; Linseed; Flax; Grassland; Clover

Efficacy & activity

Efficiacy demonstrated in field trials and extensive EU use - verified during registration.

Availability status

Current

Introduction & key dates

circa 1992

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Finland/Croatia

Date EC 1107/2009 inclusion expires

31/12/2021

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

C₉H₁₅N₅O₇S₂

Canonical SMILES

CN(S(=O)(=O)C)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

CTTHWASMBLQOFR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H15N5O7S2/c1-14(22(4,16)17)23(18,19)13-9(15)12-8-10-6(20-2)5-7(11-8)21-3/h5H,1-4H3,(H2,10,11,12,13,15)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, systemic absorbed through leaves and roots. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

120923-37-7

EC number

407-380-0

CIPAC number

515

US EPA chemical code

PubChem CID

91777

Molecular mass

369.41

PIN (Preferred Identification Name)

N-{[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamoyl}-N-methylmethanesulfonamide

IUPAC name

1-(4,6-dimethoxypyrimidin-2-yl)-3-mesyl(methyl)sulfamoylurea

CAS name

N-(4,6-dimethoxy-2-pyrimidinyl)-3-methyl-2,4-dithia-3,5-diazahexan-6-amide-2,2,4,4-tetraoxide

Other status information

PAN Listed as Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Stellaria media

Physical state

White crystalline powder

Related substances & organisms

iodosulfuron-methyl-sodium

Formulations

Property

Value

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

Artemis
Chekkar
Druid
Eagle
Squire
Sekator
Squire
Gratil

Example products using this active

Bayer CropScience
Landgold
Kingtai Chemicals

Formulation and application details

Spray application using water dispersible granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

5600

High

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

8100

Acetone

3000

Ethyl acetate

256

Toluene

n-Hexane

Melting point (°C)

179

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

185

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.75 X 10^-02

Calculated

Log P

-1.56

at 22 °C

Low

Bulk density (g ml⁻¹)

1.51

Dissociation constant pKa) at 25 °C

3.58

Weak acid

Vapour pressure at 20 °C (mPa)

0.013

Low volatility

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

5.22 X 10^-04

at pH 4.0

Non-volatile

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

Neutral solution: 201nm = 31649, 241nm = 14938, 291nm = 10
Acidic solution: 201nm = 33226, 241nm = 13978, 291nm = 20
Basic solution = 241nm = 22442, 291nm = 12

Surface tension (mN m⁻¹)

66.2

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

14.4

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

14.4

geometric mean

Note

EU 2018 dossier lab studies DT₅₀ range 2.3-68.0 days (normalised), DT₅₀ range 17.50-103 (no normalisation) days; Other data - lab studies DT₅₀ range 3-27 days (USA)

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

Note

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

Value

Stable

Note

Stable pH 7-9, DT₅₀ >365 days; DT₅₀ 34 days at pH 5

Water-sediment DT₅₀ (days)

50.1

Moderately fast

Water phase only DT₅₀ (days)

56.9

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

0.34

Mobile

K_oc

29.3

Notes and range

EU 2007 dossier K_d range 0.06-0.61 mL g⁻¹, K_oc range 3.4-84.7 mL g⁻¹, Soils=3

Freundlich

K_f

0.56

Mobile

K_foc

31.1

¹/_n

1.09

Notes and range

EU 2018 dossier K_f range 0.17-2.37 mL g⁻¹, K_foc range 5.7-81.9 mL g⁻¹, ¹/_n range 0.82-1.1, Soils=12

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.90

Calculated

High leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

1.44 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3-(4-hydroxy-6-methoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonyl-aminosulfonyl)-urea (Ref: AE-F101630)

Soil

0.496

Major fraction, Relevant

1-(5-chloro-4-hydroxy-6-methoxypyrimidin-2-yl)-3-mesyl(methyl)sulfamoylurea (Ref: BCS-C041838)

Soil

0.122

Major fraction, Relevant

1-amidino-3-mesyl(methyl)sulfamoylurea (Ref: BCS-CO41839)

Soil

0.386

Major fraction, Relevant

1-(mesyl(methyl)sulfamoyl)biuret (Ref: BCS-CQ51287)

Soil

0.063

Minor fraction; Relevant

2-amino-4,6-dimethoxypyrimidine (Ref: AE-F092944)

Soil

0.099

Minor fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-(5,6-hydroxy-4-methoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonyl-aminosulfonyl)-urea (Ref: AE-F128870)

Soil

3-(5-hydroxy-4,6-dimethoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonyl-aminosulfonyl)-urea (Ref: AE 1569309)

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

4.85

Estimated

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

>= 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 411

Rat

Moderate

(ppm diet)

> 5000

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

> 568

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

100

Coturnix japonica NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Lepomis macrochirus

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

6.41

Oncorhynchus mykiss

Moderate

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

Daphnia magna

Moderate

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

1.0

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)

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

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

0.0092

Lemna gibba

High

Non-target plants

0.07

Amaranthus retroflexus
Vegetative vigour, ER₅₀
As g ha⁻¹

1.08

Sunflower
Seedling emergence, ER₅₀
As g ha⁻¹

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

Scenedemus subspicatus

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)

> 100

Apis mellifera

Low

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

> 109.2

Apis mellifera

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)

> 100

Bombus terrestris

Low

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

> 203

Bombus terrestris

Low

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)

> 1000

Eisenia foetida

Low

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

42.5

Eisenia foetida 56 day

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

> 759

Hypoaspis aculeifer 14d

Other arthropod (1)

LR₅₀ g ha⁻¹

>
Typhlodromus pyri as g product ha⁻¹

% Effect

33.3

Mortality [Dose: 0.045 kg ha⁻¹]
Aphidius rhopalosiphi adults

Other arthropod (2)

LR₅₀ g ha⁻¹

>
Aphidius rhopalosiphi as g product ha⁻¹

% Effect

2.4

Mortality [Dose: 0.045 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 0.2 mg 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)

> 1.8

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.2

Rat SF=100

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

None allocated

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

None allocated

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

1.4

Dog SF=100

Dermal penetration studies (%)

25-75

concentration dependent

Dangerous Substances Directive 76/464

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Harmful if swallowed
Possible liver toxicant
Clastogenic and aneugenic potential of amidosulfuron not exclude

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is product is usually 9

CLP classification 2013

Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

amidosulfuron

French

amidosulfuron

German

Amidosulfuron

Danish

amidosulfuron

Italian

amidosulfuron

Spanish

amidosulfuron

Greek

Polish

amidosulfuron

Swedish

amidosulfuron

Hungarian

amidsulphuron

Dutch

amidosulfuron

Record last updated:	12/01/2021
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