Rimsulfuron (Ref: DPX E9636)

Rimsulfuron (Ref: DPX E9636)	Last updated: 12/01/2021
(Also known as: renriduron; cismethrin)

GENERAL INFORMATION

Description

A herbicide for annual grass and annual broad-leaved weed control in maize and other crops

Example pests controlled

Downy brome; Japanese brome; Barnyard grass, Crabgrass; Foxtail; Hairy fleabane; Mallow; Pigweed

Example applications

Maize; Potato; Tomato; Fruit including citrus, apples, pears, cherries, peaches, apricot, grapes; tree nuts; Pistachios

Efficacy & activity

Availability status

Current

Introduction & key dates

1991

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Slovenia/Finland

Date EC 1107/2009 inclusion expires

30/04/2021

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

Australia

Chemical structure

Isomerism

Chemical formula

C₁₄H₁₇N₅O₇S₂

Canonical SMILES

CCS(=O)(=O)C1=C(N=CC=C1)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

MEFOUWRMVYJCQC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H17N5O7S2/c1-4-27(21,22)9-6-5-7-15-12(9)28(23,24)19-14(20)18-13-16-10(25-2)8-11(17-13)26-3/h5-8H,4H2,1-3H3,(H2,16,17,18,19,20)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
rimsulfuron	-

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

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

CAS RN

122931-48-0

EC number

CIPAC number

716

US EPA chemical code

129009

PubChem CID

91779

Molecular mass

431.44

PIN (Preferred Identification Name)

N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-3-(ethanesulfonyl)pyridine-2-sulfonamide

IUPAC name

1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-pyridylsulfonyl)urea

CAS name

N-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamide

Other status information

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

Avena fatua, Kochia scoparia

Physical state

Colourless crystals

Formulations

Property

Value

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

Tarot
Titus
Basis Gold
Rigid
Matrix

Example products using this active

AgriGuard
DuPont
Makhteshim-Agan
Standon

Formulation and application details

Often supplied as water soluble granules that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

7300

High

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

14800

Acetone

35500

Dichloromethane

2850

Ethyl acetate

1550

Methanol

Melting point (°C)

172

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

174

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.47 X 10^-02

Calculated

Log P

-1.46

Low

Bulk density (g ml⁻¹)

1.5

Dissociation constant pKa) at 25 °C

Weak acid

Vapour pressure at 20 °C (mPa)

8.90 X 10^-04

Low volatility

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

8.30 X 10^-08

Non-volatile

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

pH 5: 240nm = 22400, 290nm = 481
pH 2.1: 290nm = 203
pH 1.8: 230nm = 17800, 290nm = 181

Surface tension (mN m⁻¹)

72.1

at 20.1°C 0.987g l⁻¹

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

24.3

Non-persistent

DT₅₀ (lab at 20 °C)

24.3

Non-persistent

DT₅₀ (field)

10.8

Non-persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

45.8

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 5-30 days, DT₉₀ range 71-134 days; field study DT₅₀ range 5.6-17.7 days, DT₉₀ range 19-58.8 days; Other sources: DT₅₀ 10-20 days (R3)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

1.2

Note

Published literature RL₅₀ range 0.1-2.0 days, 4 undercover crops, various matrices, n=5

Aqueous photolysis DT₅₀ (days) at pH 7

Value

11.7

Moderately fast

Note

pH sensitive: DT₅₀ 1.1 days at pH 5, 11.1 hours at pH 9, natural sunlight, 40 deg N

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

Value

7.2

Non-persistent

Note

pH sensitive: DT₅₀ 4.7 days at pH 5, 4.2 hours at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

0.9

Mobile

K_oc

50.3

Notes and range

EU dossier K_d range 0.27-1.58 mL g⁻¹, K_oc range 22.2-63.1 mL g⁻¹, Soils=4

Freundlich

K_f

0.89

Mobile

K_foc

¹/_n

0.99

Notes and range

EU dossier kf range 0.23-1.58, K_foc range 18.9-62.8 mL g⁻¹, ¹/_n range 0.9-1.22, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.41

Calculated

Transition state

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

Value

5.93 X 10^-02

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

N-(4,6-dimethoxy-2-pyrimidinyl)-N-(3-(ethylsulfonyl)-2-pyridinyl)urea (Ref: IN-70941)

Soil

0.545

Major fraction, Relevant

N-(3-(ethylsulfonyl)-2-pyridinyl)-4,6-dimethyoxy-2-pyrimidinamine (Ref: IN-70942)

Soil

0.235

Major fraction, Relevant

3-(ethylsulfonyl)-2-pyridinesulfonamide (Ref: IN-E9260)

Soil

0.189

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2-[[3-ethylsulfonyl)-2-pyridinyl]amino]-6-methoxy-4(1H)-pyrimidinone (Ref: IN-JF 999)

Soil; Water/sediment

4,6-dimethoxy-2-pyrimidinamine (Ref: IN-J 290)
Note: Possible groundwater contaminant

Plant; Water/sediment

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 3.4

Rat

High

(ppm diet)

> 50

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

165

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Anas platyrhynchos

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

142

Colinus virginianus NOAED

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 390

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

125

Oncorhynchus mykiss

Low

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

> 360

Daphnia magna

Low

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

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

110.0

Americamysis bahia

Low

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)

0.009

Lemna gibba EU: 0.046 L. minor

High

Non-target plants

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

1.2

Selenastrum Capricornutum

Moderate

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

0.63

Unknown species

Moderate

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)

27.9

Apis mellifera

Moderate

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)

> 1000

Eisenia foetida

Low

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

% Effect

14 / 1

Mortality / Parasitism [Dose: 150 kg ha⁻¹]
Aphidius rhopalosiphi imagine

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

9 / 0

Mortality / Fertility [Dose: 4.4 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: Not stated

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)

> 5.4

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)

None 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)

0.07

Dog SF=100

Dermal penetration studies (%)

70.0

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Minimal risk to workers

European MRLs

EU MRL pesticide database

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 and kidney toxicant

Handling issues

Property

Value and interpretation

General

Prevent generation of dust or mists
Not explosive
IMDG Transport Code is usually 9

CLP classification 2013

Health: H314, H319
Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R20, R53

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

rimsulfuron

French

rimsulfuron

German

Rimsulfuron

Danish

rimsulfuron

Italian

rimsulfuron

Spanish

rimsulfuron

Greek

Polish

rimsulfuron

Swedish

rimsulfuron

Hungarian

rimszulfuron

Dutch

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