Azimsulfuron

Azimsulfuron	Last updated: 16/05/2024
(Also known as: DPX A 8947; DPX 47)

SUMMARY

A sulfonylurea herbicide for the control of a range of broad-leaved and sedge weeds in paddy fields and other crops. It is highly soluble in water, semi-volatile and, based on its physico-chemical properties, appears to have potential for leaching to groundwater. It is not expected to be persistent in the field but can be persistent in water systems. It has a low mammalian toxicity but has high potential for bioaccumulation. No adverse health effects have been identified. Azimsulfuron is moderately toxic to algae, honeybees and earthworms but less so to birds and fish.

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 High alert: Drainflow: Mobile	Ecotoxicity Moderate alert: Fish chronic ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A post-emergence pyrimidinylsulfonylurea herbicide for the control of a range of broad-leaved and sedge weeds in paddy fields and other crops

Example pests controlled

Cyperus spp.; Fimbristylis miliacea; Barnyard grass; Water plantain; Arrowhead; Dirty Dora; Spikerush; Starfruit; Alisma

Example applications

Paddy fields; Aquatic situations

Efficacy & activity

Availability status

Current

Introduction & key dates

1995, introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

UK LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Spain/France

Date EC 1107/2009 inclusion expires

Expired

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

Australia

Chemical structure

Isomerism

None

Chemical formula

C₁₃H₁₆N₁₀O₅S

Canonical SMILES

CN1C(=C(C=N1)C2=NN(N=N2)C)S(=O)(=O)NC(=O)NC3=NC(=CC(=N3)OC)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

MAHPNPYYQAIOJN-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H16N10O5S/c1-22-11(7(6-14-22)10-18-21-23(2)19-10)29(25,26)20-13(24)17-12-15-8(27-3)5-9(16-12)28-4/h5-6H,1-4H3,(H2,15,16,17,20,24)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
azimsulfuron	-

General status

Pesticide type

Herbicide

Substance groups

Sulfonylurea herbicide; Pyridine compound; Pyrazole herbicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, absorbed by foliage. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

120162-55-2

EC number

601-676-5

CIPAC number

584

US EPA chemical code

129115

PubChem CID

86355

CLP index number

613-163-00-3

Molecular mass

424.40

PIN (Preferred Identification Name)

N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide

IUPAC name

1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-ylsulfonyl]urea

CAS name

N-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide

Other status information

Australian NOHSC List of Designated Hazardous Substances

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Cyperus difformis, Echinochloa colona, Lindernia dubia

Physical state

White powdery solid

Formulations

Property

Value

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

DuPont

Example products using this active

Gulliver
Azimsulfuron 50WG
Segment

Formulation and application details

May be supplied as water-dispersible granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1050

High

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

26400

Acetone

13000

Ethyl acetate

2100

Methanol

1800

Toluene

Melting point (°C)

170

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

180

Flashpoint (°C)

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

3.98 X 10^-02

Calculated

Log P

-1.4

at 25 °C

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.12

Dissociation constant pKa) at 25 °C

3.6

Weak acid

Vapour pressure at 20 °C (mPa)

4.00 X 10^-06

Low volatility

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

5.00 X 10^-10

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

2,7

24 hr

Volatilisation is potentially a concern for short and long range air transport

From soil surface

12.9

24 hr

Volatilisation is not considered critical for air pollution

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

242nm = 23014, 23988, 24099

Surface tension (mN m⁻¹)

68.1

at 24 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Unflooded soil

Moderately persistent

DT₅₀ (lab at 20 °C)

64.2

Unflooded soil

Moderately persistent

DT₅₀ (field)

3.5

Non-persistent

DT₉₀ (lab at 20 °C)

166

Unflooded soil

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 17.3-133 days & DT₉₀ range 66.6-529 days for non-flooded situations, DT₅₀ range 12.1-51.0 days & DT₉₀ range 58.7-169 day whole system; Other literature studies give field DT₅₀ 2-5 days; Australian registration dossier 18-134 days European soils (A5)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

3.3

Note

Rice, whole plant, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

164

Stable

Note

pH sensitive: 103 days at pH 5, 225 days at pH 9, all at 20 °C

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

Value

124

Persistent

Note

pH sensitive: 89 days at pH 5, 124 days at pH7, 132 days at pH 9 all at 26 °C

Water-sediment DT₅₀ (days)

112

Slow

Water phase only DT₅₀ (days)

44.5

Stable

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)

1.14

Mobile

K_oc (mL g⁻¹)

73.8

Notes and range

EU dossier K_d range 0.69-1.65 mL g⁻¹, K_oc range 48-94 mL g⁻¹, Soils=4

Freundlich

K_f (mL g⁻¹)

1.11

Mobile

K_foc (mL g⁻¹)

68.6

¹/_n

0.93

Notes and range

EU dossier K_f range 0.75-1.31 mL g⁻¹, K_foc range 54-78 mL g⁻¹, ¹/_n range 0.88-0.98, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.18

Calculated

Low leachability

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

Value

2.77 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

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

0.632

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

N-((4-hydroxy-6-methoxypyrimidin-2-yl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide (Ref: IN JJ999)

Major fraction

0.13

1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide (Ref: IN A8342)

Major fraction

0.280

Data for upland soil

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

Major fraction

0.24

Data for upland soi

N-(((aminoiminomethyl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulphonamide (Ref: IN KQ962)

Major fraction

0.13

Data for upland soil

N-((4-hydroxy-6-methoxypyrimidin-2-yl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide (Ref: IN JJ999)

Minor fraction

0.02

Data for upland soi

1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide (Ref: IN A8342)

Minor fraction

0.06

Data for flooded soil

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

Minor fraction

0.03

Data for flooded soil

N-(((aminoiminomethyl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulphonamide (Ref: IN KQ962)

Minor fraction

0.075

Data for flooded soil

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-amino-6-methoxy-4-pyrimidinol (Ref: IN-H92350)

N-(4,6-dimethoxy-2-pyrimidinyl)-beta-D-glucopyranosylamine

N-glucosyl-J0290; glucosyl-J0290

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)

Rat 2 yr

(ppm diet)

> 1000

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

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

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

> 1000

Eisenia foetida

Low

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

12.5

Eisenia foetida 56 day

Moderate

Soil micro-organisms

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

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

2.64

Onion
Seedling emergence, ER₅₀
as g product 50DF ha⁻¹

0.45

Sugarbeet
Vegetative vigour, ER₅₀
as g product 50DF ha⁻¹

Honeybees (Apis spp.)

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

> 25

Apis mellifera

Moderate

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

> 200

Apis mellifera

Low

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

Chronic

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

> 58.8

Aphidius rhopalosiphi

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

> 54.3

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)

154

Oncorhynchus mykiss

Low

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

6.3

Oncorhynchus mykiss

Moderate

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

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

378

Daphnia magna

Low

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

5.4

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)

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

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

0.00062

Lemna gibba

High

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

0.011

Pseudokirchneriella subcapitata

Moderate

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

0.003

Selenastrum capricornutum

Moderate

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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.94

Rat 4 hr

Other Mammal toxicity endpoints

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

0.1

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

Not allocated

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

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

0.1

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders for proposed uses

Occupational

Occupational exposure possible during product handling - PPE/PPC advised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible pancreas toxicant
Possible liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

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

azimsulfuron

French

azimsulfuron

German

Azimsulfuron

Danish

azimsulfuron

Italian

azimsulfuron

Spanish

azimsulfuron

Greek

azimsulfuron

Polish

azymsulfuron

Swedish

Hungarian

Dutch

azimsulfuron

Norwegian

Record last updated:	16/05/2024
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