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orthosulfamuron (Ref: IR5878)
** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

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 Click here for an explantaion of the general chemical status information
for orthosulfamuron

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

EC Regulation 1107/2009 (repealing 91/414):
Status Not approved
Dossier rapporteur/co-rapporteur Italy
Date inclusion expires Not applicable
EU Candidate for substitution (CfS) -
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: USA

Chemical structure: Click here for further information on the general chemical status information used on this site
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: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group Pyrimidinylsulfonylurea
Minimum active substance purity 985mg/kg
Known relevant impurities EU dossier: Dichloromethane, maximum content 1 g/kg
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 (g mol-1) 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) Not known
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
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Isagro USA
Example products using this active
  • Strada
  • Kelion
  • Percutio
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Usually supplied as a water-dispersible granular formulation.


ENVIRONMENTAL FATE

for orthosulfamuron

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 629 A5 High
Solubility - In organic solvents at 20oC (mg l-1) 19500 A5 - Acetone -
3300 A5 - Ethyl acetate -
8300 A5 - Methanol -
56000 A5 - 1,2-Dichloromethane -
Melting point (oC) 157 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 185 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 2.04 X 1001 Calculated -
Log P 1.31 A5 Low
Bulk density (g ml-1)/Specific gravity 1.48 L3 -
Dissociation constant (pKa) at 25oC - - -
Note:
Vapour pressure at 20oC (mPa) 0.112 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 7.6 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 6.58 Calculated High leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 2.96 X 10-01 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Low
Maximum UV-vis absorption L mol-1 cm-1 Neutral soln.: 238nm=21100
Acidic soln.: 236nm=19500
Basic soln.: 241.0nm=27900
A5 -
Surface tension (mN m-1) 71.4 A5 at 22degC -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 12.5 A4 Non-persistent
DT50 (lab at 20oC) 12.5 A4 Non-persistent
DT50 (field) - - -
DT90 (lab at 20oC) 41.5 A4 -
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 A5 - -
Note Not considered to be a significant route of degradation
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 24.4 A5 Non-persistent
Note pH and temperature sensitive: DT50 8 hours at pH 5, 228 days at pH 9, all at 25 degC; 0.4 hours at pH 4, 1.5 days at pH 7, 8 days at pH 9 all at 50 deg C.
Water-sediment DT50 (days) 30.3 A5 Moderately fast
Water phase only DT50 (days) 19.8 A5 Slow

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 6.73 A5 Moderately mobile
Koc 352.5
Notes and range EU dossier Kd range 6.003-8.568 mL/g, Koc range 249-550 mL/g, soil=4
Freundlich Kf 5.41 A5 -
Kfoc nd
1/n 0.871
Notes and range EU dossier Kf range 3.763-6.662mL/g, Kfoc not calculated, 1/n range 0.749-0.920, soils=4
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
2-((dimethylamino)carbonyl)phenyl sulfamic acid (Ref: IR7863) This metabolite may cause environmental pollution, click here for further information Soil   0.545   Major farction, Relevant
N-(4,6-dimethoxypyrimidin-2-yl) urea (Ref: IR7825) This metabolite may cause environmental pollution, click here for further information Soil   0.570   Major fraction, Relevant
1-(4-methoxy-6-hydroxypyrimidin-2-yl)-3-(2,(2-dimethylcarbomyl)phenylsulfomoyl)urea (Ref: IR 8181) This metabolite may cause environmental pollution, click here for further information 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

for orthosulfamuron

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 1.0 A5 Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) > 100 A5 Brachidanio rerio Low
Fish - Chronic 21 day NOEC (mg l-1) 6.1 A5 Pimephales promelas Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 100 A5 Daphnia magna Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 10 A5 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 A5 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 A5 Lemna gibba, fronds High
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 13 A5 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 A5 Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 109.4 A5 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 A5 Eisenia foetida Low
Earthworms - Chronic NOEC, reproduction (mg kg-1) > 1000 A5 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
A5
Dose: 0.507mg/Kg soil, 42 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for orthosulfamuron

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 2.19 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.05 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.70 A5 Rabbit, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.05 A5 Rat, SF=300 -
Dermal penetration studies (%) 0.54-2.63 A4 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public Acceptable for proposed uses
Occupational Acceptable for proposed uses
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A3; B0; C3; D0; E3

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

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
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Health: H361d
Environment: H400
EC Risk Classification Click here to view information omn the EU risk phrases Reproduction risk category 3: R63
N - Dangerous for the environment: R50
EC Safety Classification Click here to view information omn the EU safety phrases S2, S13, S20/21, S57, S60
WHO Classification NL - Not listed
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for orthosulfamuron

Language Name
English orthosulfamuron
French -
German -
Danish -
Italian -
Spanish ortosulfamuron
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -

Record last updated: Wednesday 26 June 2019
Contact: aeru@herts.ac.uk