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Primisulfuron
Last updated: 02/03/2021
(Not known by any other names)
GENERAL INFORMATION
Description
An urea herbicide used on crop and non-crop areas for the control of grass and many broad-leaved weeds
Example pests controlled
Grasses including Kentucky bluegrass; Broad-leaved weeds
Example applications
Corn; Non-cropped areas
Efficacy & activity
-
Availability status
Unknown
Introduction & key dates
1990
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
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
Not applicable
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
                 
Also used in
Also used in
-
Chemical structure
Isomerism
None
Chemical formula
C₁₄H₁₀F₄N₄O₇S
Canonical SMILES
C1=CC=C(C(=C1)C(=O)O)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC(F)F)OC(F)F
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
GPGLBXMQFQQXDV-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C14H10F4N4O7S/c15-11(16)28-8-5-9(29-12(17)18)20-13(19-8)21-14(25)22-30(26,27)7-4-2-1-3-6(7)10(23)24/h1-5,11-12H,(H,23,24)(H2,19,20,21,22,25)
2D structure diagram/image available?
Yes
General status
Pesticide type
Herbicide, Metabolite
Metabolite Type
Soil
Substance group
Sulfonylurea
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Selective, systemic, absorbed through roots and foliage. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
CAS RN
113036-87-6
EC number
-
CIPAC number
712
US EPA chemical code
-
PubChem CID
91774
Molecular mass
454.31
PIN (Preferred Identification Name)
-
IUPAC name
2-[4,6-bis(difluoromethoxy)pyrimidin-2-ylcarbamoylsulfamoyl]benzoic acid
CAS name
2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
B
Herbicide Resistance Classification (WSSA)
2
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
Amaranthus hybridus, Amaranthus rudis, Sorghum bicolor
Physical state
Colourless crystalline solid
Can be a metabolite of:
Parent
Formation medium
Estimated maximum occurrence fraction
1107/2009 relevancy
primisulfuron methyl Soil - -
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
-
Example products using this active
-
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
70
M4 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems) (click here )
4 = Verified data
 Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
35000
P4 P = Other governments and regulators
4 = Verified data
Acetone		 -
1000
P4 P = Other governments and regulators
4 = Verified data
Ethanol		 -
570
P4 P = Other governments and regulators
4 = Verified data
Toluene		 -
1.5
P4 P = Other governments and regulators
4 = Verified data
n-Hexane		 -
Melting point (°C)
196.1
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
1.58 X 1000 Calculated -
Log P
0.2
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low
Bulk density (g ml⁻¹)
1.64
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
3.47
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Weak acid
Vapour pressure at 20 °C (mPa)
5.00 X 10-03
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
4.00 X 10-02
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-volatile
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
30
M4 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems) (click here )
4 = Verified data
 Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
16
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Field studies DT₅₀ range 4-29 days. Other studies DT₅₀ 31–62 days (P3)
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
248
P4 P = Other governments and regulators
4 = Verified data
 Stable
Note
DT₅₀ 20.6 at pH 5, natural sunlight conditions, 30 days
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
P4 P = Other governments and regulators
4 = Verified data
 Stable
Note
Stable pH 7 to pH 9, hydrolysis does occur under acidic conditions, DT₅₀ 25 days at pH 5
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
M3 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems) (click here )
3 = Unverified data of known source
 Mobile
Koc
50
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
2.77 Calculated Transition state
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
1.40 X 10-01 Calculated -
Note
-
Potential for particle bound transport index
Low Calculated -
Potential for loss via drain flow
Mobile Calculated -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
Low risk
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Based on LogP < 3		 Low risk
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5050
P2 P = Other governments and regulators
2 = Unverified data of unknown source
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)
2150
P2 P = Other governments and regulators
2 = Unverified data of unknown source
Anas platyrhynchos		 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)
24
P2 P = Other governments and regulators
2 = Unverified data of unknown source
Oncorhynchus mykiss		 Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
13
P4 P = Other governments and regulators
4 = Verified data
Oncorhynchus mykiss		 Low
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
260
P4 P = Other governments and regulators
4 = Verified data
Daphnia magna		 Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.42
P4 P = Other governments and regulators
4 = Verified data
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)
0.8
P4 P = Other governments and regulators
4 = Verified data
Lemna gibba		 Moderate
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
0.012
P4 P = Other governments and regulators
4 = Verified data
Pseudokirchneriella subcapitata		 Moderate
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
P4 P = Other governments and regulators
4 = Verified data
 Moderate
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
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
P4 P = Other governments and regulators
4 = Verified data
 Moderate
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
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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)
> 5050
P2 P = Other governments and regulators
2 = Unverified data of unknown source
Rat		 Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Mouse		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
4.8
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.13
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
List II - -
Exposure Routes
Public
-
Occupational
Occupational exposure may occur through dermal contact
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
?Possibly, status not identified
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
XNo, known not to cause a problem
XNo, known not to cause a problem
 No data found
Respiratory tract irritant Skin irritant Skin sensitiser
XNo, known not to cause a problem
XNo, known not to cause a problem
 No data found
Eye irritant Phototoxicant  
XNo, known not to cause a problem
 No data found  
General human health issues
Possible liver and kidney toxicant at high doses
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Environment: H400, H410
EC Risk Classification
N - Dangerous for the environment: R50/53
EC Safety Classification
None allocated at this time
WHO Classification
U (Unlikely to present an acute hazard)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
primisulfuron
French
primisulfuron
German
Primisulfuron
Danish
primisulfuron
Italian
primisulfuron
Spanish
primisulfuron
Greek
-
Polish
primisulfuron
Swedish
-
Hungarian
-
Dutch
-
Record last updated: 02/03/2021
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