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GET ADDITIONAL DATA HERE!

topramezone (Ref: BAS 670 H)
** Translations

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

SUMMARY

Topramezone is a post-emergence herbicide currently being evaluated for use within the EU. It is highly soluble in water, non-volatile but, based on its chemical properties, has a high risk of leaching to groundwater. It can be persistent in both soil and aquatic systems. It is moderately toxic to mammals but a low potential for bioaccumulation. It is classified as an irritant. It is moderately toxic to birds, honey bees, earthworms, fish and aquatic invertebrates.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for topramezone

Description: A post-emergence herbicide for broad-leaved weeds and grasses used mainly on corn

Example pests controlled: Giant foxtail; Broad-leaved signal grass; Crabgrass; Goosegrass; Woolly cupgrass; Shattercane; Johnsongrass; Barnyardgrass

Example applications: Field corn (grain, silage, seed); Sweetcorn; Popcorn

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 2006

EC Regulation 1107/2009 (repealing 91/414):
Status Pending
Dossier rapporteur/co-rapporteur France
Date inclusion expires -
EU Candidate for substitution (CfS) No data
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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism None
Chemical formula C16H17N3O5S
Canonical SMILES CC1=C(C=CC(=C1C2=NOCC2)S(=O)(=O)C)C(=O)C3=CNN(C3=O)C
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) IYMLUHWAJFXAQP-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C16H17N3O5S/c1-9-10(15(20)11-8-17-19(2)16(11)21)4-5-13(25(3,22)23)14(9)12-6-7-24-18-12/h4-5,8,21H,6-7H2,1-3H3
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 Benzoylpyrazole
Minimum active substance purity 970 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Systemic, highly selective, rapidly absorbed and translocated
CAS RN 210631-68-8
EC number -
CIPAC number 800
US EPA chemical code 123009
PubChem CID 11302979
Molecular mass (g mol-1) 363.39
PIN (Preferred Identification Name) [3-(4,5-dihydro-1,2-oxazol-3-yl)-4-(methanesulfonyl)-2-methylphenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
IUPAC name [3-(4,5-dihydro-1,2-oxazol-3-yl)-4-mesyl-o-tolyl](5-hydroxy-1-methylpyrazol-4-yl)methanone
CAS name [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
Other status information PAN Bad Actor
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 White crystalline solid
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
  • Avmac
  • BASF
  • Bayer CropScience
Example products using this active
  • Pylex
  • BAS 670 00H
  • Armezon
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Formulations include suspension concentrates.


ENVIRONMENTAL FATE

for topramezone

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) 100000 A5 High
Solubility - In organic solvents at 20oC (mg l-1) 10000 A5 - Acetone -
10000 A5 - Toluene -
10000 A5 - n-Heptane -
10000 A5 - Ethyl acetate -
Melting point (oC) 220.9 A5 -
Boiling point (oC) - - -
Degradation point (oC) 300 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 3.02 X 10-02 Calculated -
Log P -1.52 A5 Low
Bulk density (g ml-1)/Specific gravity 1.406 A5 -
Dissociation constant (pKa) at 25oC 4.06 A5 -
Note: Weak acid
Vapour pressure at 20oC (mPa) 1.10 X 10-09 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 7.13 X 10-14 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 4.75 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 3.65 X 10+00 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 Medium
Maximum UV-vis absorption L mol-1 cm-1 207nm = 27077, 272nm = 8601, 300nm = 5800, 410nm = 96 A5 -
Surface tension (mN m-1) 69.0 A5 at 20oC, 1% solution -

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) 218 A5 Persistent
DT50 (lab at 20oC) 218 A5 Persistent
DT50 (field) 26.1 A4 Non-persistent
DT90 (lab at 20oC) 763 A5 -
DT90 (field) 529 A4 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 85-357 days, DT90 range 283-greater than 1000 days; field studies DT50 range 10.8-69.3 days, DT90 range 184-greater than 1000 days. Other studies: Lab DT50 range 125-495 days, field studies range 3-29 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 Data for sterile buffer solution at pH 5 and pH9, slow degradation in natural water DT50 72 days continuous irradiation
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 9at 25 degC, 30 days
Water-sediment DT50 (days) 77.5 A5 Moderately fast
Water phase only DT50 (days) 9.5 A5 Moderately fast

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 - P4 Moderately mobile
Koc 171
Notes and range Canadian dossier gives Koc range 38-303 mL/g
Freundlich Kf 1.78 A5 Moderately mobile
Kfoc 93
1/n 0.86
Notes and range EU dossier Kf range 0.165-6.33, Kfoc range 15.0-296.7 mL/g, 1/n range 0.786-0.923
pH sensitivity Adsorption stronger on more acidic soils

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
3-(4,5-dihydro-isoxazol-3-yl)-4-methanesulfonyl-2-methyl-benzoic acid (Ref: M670H05) This metabolite may cause environmental pollution, click here for further information Soil   0.192   Major fraction, Relevant
(3-cyano-4-methanesulfonyl-2-methyl phenyl)(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone (Ref: M670H01) Soil   -   Minor fraction, Not relevant
6-(5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl)-5-methyl-2,3-dihydro-4H-1-benzothiopyran-4-one (Ref: M670H10) Soil   -   Minor fraction, Not relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
(Ref: M670H02) hydroxy topramezone Plant; Animal - -
(Ref: M670H03) topramezone des-N-methyl Plant - -
(Ref: M670H04) demethyl hydroxy topramezone Animal - -
(Ref: M670H08) topramezone methyl ketone Plant - -


ECOTOXICOLOGY

for topramezone

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) 0.3 A5 Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 0.5 P4 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 1085 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) > 100 A5 Oncorhynchus mykiss Low
Fish - Chronic 21 day NOEC (mg l-1) 0.01 P4 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 100 A5 Daphnia magna Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 97.5 P4 Daphnia magna Low
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) 0.009 A5 Lemna gibba High
Non-target plants 46.1 A5 Onion
Seedling emergence, ER50
as mL product/ha (BASS 670 00 Conc 336 g/L)
-
17 Ar Buckwheat
Vegetative vigour, ER70
as mL product/ha (BASS 670 00 Conc 336 g/L)
-
Algae - Acute 72 hour EC50, growth (mg l-1) 17.2 A5 Pseudokirchneriella subcapitata Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) 3 P4 Pseudokirchneriella subcapitata Low
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 72.05 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 1000 A5 Eisenia foetida Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 0.672 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect 37.2 A5 Folsomia candida, NOEC mg kg-1 -
Other arthropod (1) LR50 g ha-1 100 >, Mortality
A5 Aphidius rhopalosiphi, adult
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 105 Mortality
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.67 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for topramezone

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) > 2000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.4 A5 Rat, 4 hr (head & nose) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.001 A5 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.001 A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.0006 A5 -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Negligible risk to bystanders
Occupational Possible risk on re-entry of sprayed areas
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) 0.1 EU Dir 89/778/EC limit; A5 Calc MAC=12 μg l-1 -

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

-

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

General human health issues Eye, liver, kidney, pancreas, and thyroid toxicant
USEPA - possible human carcinogen at high doses

: 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
IMDG Transport Code is usually 9
CLP classification 2013 None allocated at this time
EC Risk Classification Click here to view information omn the EU risk phrases Reproduction risk category 2: R61
N - Dangerous for the environment: R50/53
EC Safety Classification Click here to view information omn the EU safety phrases S45, S53, S60, S61
WHO Classification NL - Not listed
US EPA Classification (formulation) No consensus across products or no products available - -
UN Number Usually 3077
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for topramezone

Language Name
English topramezone
French -
German Topramezone
Danish topramezone
Italian topramezone
Spanish topramezona
Greek -
Slovenian topramezon
Polish topramezone
Swedish -
Hungarian -
Dutch topramezone

Record last updated: Wednesday 30 May 2018
Contact: aeru@herts.ac.uk