Orthosulfamuron (Ref: IR5878)

Orthosulfamuron (Ref: IR5878)	Last updated: 24/02/2021
(Not known by any other names)

SUMMARY

A herbicide currently being assessed for usage within in the EU. It is highly soluble in water, volatile and, based on its chemical properties, there is a high risk of ot leaching to groundwater. It tends not to be persistent in either soil or aquatic systems. It has a low mammalian toxicity and not thought to bioaccumulate. However, there are some concerns that it may be neurotoxic and be a reproduction/development toxin. It has a low to moderate toxicity to most biodiversity.

GENERAL INFORMATION

Description

Pre- and post-emergence rice herbicide active against grasses and some broad-leaved weeds

Example pests controlled

Sedges including flatsedge; Grass weeds including Barnyardgrass; Velvetleaf; Water-plantain; Mud-plantain; Sagittaria; False pimpernel

Example applications

Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1998; 2007, USA

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Italy

Date EC 1107/2009 inclusion expires

Not applicable

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

USA

Chemical structure

Isomerism

Chemical formula

C₁₆H₂₀N₆O₆S

Canonical SMILES

CN(C)C(=O)C1=CC=CC=C1NS(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UCDPMNSCCRBWIC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H20N6O6S/c1-22(2)14(23)10-7-5-6-8-11(10)20-29(25,26)21-16(24)19-15-17-12(27-3)9-13(18-15)28-4/h5-9,20H,1-4H3,(H2,17,18,19,21,24)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Pyrimidinylsulfonylurea

Minimum active substance purity

985mg kg⁻¹

Known relevant impurities

EU dossier: Dichloromethane, maximum content 1 g kg⁻¹

Substance origin

Synthetic

Mode of action

Systemic, systemic absorbed by foliage and roots and translocated, acetohydroxy acid synthase

CAS RN

213464-77-8

EC number

CIPAC number

781

US EPA chemical code

108209

PubChem CID

11091168

Molecular mass

424.44

PIN (Preferred Identification Name)

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

IUPAC name

1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)phenylsulfamoyl]urea

CAS name

2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]amino]-N,N-dimethylbenzamide

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

Physical state

Fine white, odourless powder

Formulations

Property

Value

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

Strada
Kelion
Percutio

Example products using this active

Isagro USA

Formulation and application details

Usually supplied as a water-dispersible granular formulation

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

629

High

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

19500

Acetone

3300

Ethyl acetate

8300

Methanol

56000

1,2-Dichloromethane

Melting point (°C)

157

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

2.04 X 10⁰¹

Calculated

Log P

1.31

Low

Bulk density (g ml⁻¹)

1.48

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.112

Low volatility

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

7.6 X 10^-05

Non-volatile

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

Neutral soln.: 238nm=21100
Acidic soln.: 236nm=19500
Basic soln.: 241.0nm=27900

Surface tension (mN m⁻¹)

71.4

at 22°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

12.5

Non-persistent

DT₅₀ (lab at 20 °C)

12.5

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

41.5

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier (DAR) lab studies DT₅₀ range 1.9-25 days, DT₉₀ range 6.4-83 days; Isagro datasheet gives DT₅₀ 20-80 days; Other literature DT₅₀ ranges 10-21 days

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

Not considered to be a significant route of degradation

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

Value

24.4

Non-persistent

Note

pH and temperature sensitive: DT₅₀ 8 hours at pH 5, 228 days at pH 9, all at 25 °C; 0.4 hours at pH 4, 1.5 days at pH 7, 8 days at pH 9 all at 50 °C.

Water-sediment DT₅₀ (days)

30.3

Moderately fast

Water phase only DT₅₀ (days)

19.8

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

6.73

Moderately mobile

K_oc

352.5

Notes and range

EU dossier K_d range 6.003-8.568 mL g⁻¹, K_oc range 249-550 mL g⁻¹, soil=4

Freundlich

K_f

5.41

K_foc

¹/_n

0.871

Notes and range

EU dossier K_f range 3.763-6.662mL g⁻¹, K_foc not calculated, ¹/_n range 0.749-0.920, soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.59

Calculated

Low leachability

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

Value

3.03 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-((dimethylamino)carbonyl)phenyl sulfamic acid (Ref: IR7863)

Soil

0.545

Major farction, Relevant

N-(4,6-dimethoxypyrimidin-2-yl) urea (Ref: IR7825)

Soil

0.570

Major fraction, Relevant

1-(4-methoxy-6-hydroxypyrimidin-2-yl)-3-(2,(2-dimethylcarbomyl)phenylsulfomoyl)urea (Ref: IR 8181)

Soil

0.224

Minor fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

1,-(4-methoxy-6-hydroxypyrimidin-2-yl)-3-(2-(methylcarbomoyl)phenylsulfomoyl)urea

N-desm-O-desm IR5878

Rat; Animals

2-amino-N,N-dimethylbenzamide

DB amine

Rat; Plants (rice, crops); Animals; Soil

2-sulfamoylamino-N,N-dimethylbenzamide

DBS amide

Rat; Plants (rice, crops); Soil

Pyr-O-Glucur IR5878

Rat

N-desmethyl IR5878

Rat; Animals

Pyr-O-Glucur DOP urea

Rat

(4,6-dimethoxy-5-sulfate pyrimidin-2-yl)urea

Pyr-O-Sulf DOP Urea

Rat; Animals

2-amino-N-methylbenzamide

N-desmethyl DB amine

Animals

Pyr-OH DOP urea

Animals

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1.0

Low potential

CT₅₀ (days)

Not available

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)

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Brachidanio rerio

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

6.1

Pimephales promelas

Moderate

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

> 100

Daphnia magna

Low

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

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)

66.9

Chironomus riparius

Low

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

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

0.00033

Lemna gibba fronds

High

Non-target plants

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

Anabaena flos-aquae

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

Low

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

> 109.4

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)

> 1000

Eisenia foetida

Low

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

> 1000

Eisenia foetida

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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

Dose: 0.507mg/Kg soil 42 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)

> 2.19

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.05

Rat SF=100

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

0.70

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)

0.05

Rat SF=300

Dermal penetration studies (%)

0.54-2.63

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

; ; ; ;

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

May be absorbed through skin or inhalation
Possible liver, spleen and kideny toxicant
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H361d
Environment: H400

EC Risk Classification

Reproduction risk category 3: R63
N - Dangerous for the environment: R50

EC Safety Classification

S2, S13, S20/21, S57, S60

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

orthosulfamuron

French

German

Danish

Italian

Spanish

ortosulfamuron

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	24/02/2021
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