| pyrasulfotole (Ref: AE 0317309 ) |
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GENERAL INFORMATION 
Description: A novel herbicide for post-emergent control of various broad-leaved weeds, used with the safener mefenpyr-diethyl
Availability status: Current
Introduction & key dates: 2004, Australia, Canada, 2007, USA
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not applicable |
| Dossier rapporteur/co-rapporteur | Not applicable |
| Date inclusion expires | Not applicable |
| EU Candidate for substitution (CfS) | Not applicable |
| Listed in EU database | Yes |
Approved for use (
) or known to be used (
) in the following European countries: 
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 |
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Also used in: USA, Canada, Australia
Chemical structure:
| Isomerism | - |
| Chemical formula | C14H13F3N2O4S |
| Canonical SMILES | CC1=C(C(=O)N(N1)C)C(=O)C2=C(C=C(C=C2)C(F)(F)F)S(=O)(=O)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | CZRVDACSCJKRFL-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C14H13F3N2O4S/c1-7-11(13(21)19(2)18-7)12(20)9-5-4-8(14(15,16)17)6-10(9)24(3,22)23/h4-6,21H,1-3H3 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Other substance | |||
| Other constituent type | Herbicide safener | |||
| Substance group | Pyrazolone | |||
| Minimum active substance purity | - | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Selective, acts by the inhibition of carotenoid biosynthesis specifically inhibits the enzyme 4- hydroxyphenylpyruvate dioxygenase (HPPD). | |||
| CAS RN | 365400-11-9 | |||
| EC number | - | |||
| CIPAC number | - | |||
| US EPA chemical code | 000692 | |||
| PubChem CID | - | |||
| Molecular mass (g mol-1) | 244.3 | |||
| PIN (Preferred Identification Name) | (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)[2-(methanesulfonyl)-4-(trifluoromethyl)phenyl]methanone | |||
| IUPAC name | (5-hydroxy-1,3-dimethylpyrazol-4-yl)(a,a,a-trifluoro-2-mesyl-p-tolyl)methanone | |||
| CAS name | (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone | |||
| 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 | Beige coloured powder | |||
| Related substances & organisms | ||||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | Not applicable | |||
| Formulation and application details | - | |||
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 69100 | F3 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 21600 | F3 - Ethanol | - | |
| 6860 | F3 - Toluene | - | ||
| 89200 | F3 - Acetone | - | ||
| 37200 | F3 - Ethyl acetate | - | ||
| Melting point (oC) | 201 | F3 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | - | - | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 4.37 X 10-02 | Calculated | - |
| Log P | -1.36 | F3 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.53 | P3 | - | |
| Dissociation constant (pKa) at 25oC | 4.2 | F3 | - | |
| Note: Weak acid | ||||
| Vapour pressure at 20oC (mPa) | 2.7 X 10-04 | F3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | - | - | - | |
GUS leaching potential index  |
2.50 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.56 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | Absoption max at 264nm and 241nm in water, 0.1M HCl, 0.1M NaOH respectively | F4 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 55.5 | P4 | Moderately persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | DT50 range 42-16 days and 77-87 days in bare soil and cropped soil, respectively | |||
| 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 | P3 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | P3 | - |
| Note | - | |||
| Water-sediment DT50 (days) | 365 | P2 | Stable | |
| Water phase only DT50 (days) | 140 | P2 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | P4 | Moderately mobile |
| Koc | 368 | |||
| Notes and range | Koc range 21.6 (clay loam) to 715 (sandy loam) mL/g | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 2-methylsulfonyl-4-trifluoromethylbenzoic acid (Ref: AE-B197555) | Soil | 0.093 | Minor fraction, Relevancy unknown | |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | Low risk | P3 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | F4 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | 2000 | P3 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 93.5 | P3 Lepomis macrochirus | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.58 | P3 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 93.3 | P3 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 12.8 | P3 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) | 0.98 | P3 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 30.0 | P3 Pseudokirchneriella subcapitata | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 2.6 | P3 Selenastrum capricornutum | Low | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 75.0 | P3 | 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 | P3 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 113 | P3 Typhlodromus pyri | - |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 80.3 | P3 Aphidius rhopalosiphi | - |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
P3 Dose: 0.25 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | F4 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | F4 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 5.03 | F4 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.01 | F3 Rat, SF=100, Australia | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.2 | F3 Rat, SF=1000, Australia | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | - | - | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | Operators should use full PPE to minimise exposure | |||
| 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 | |||
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A3; B0; C0; D0; E3 |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Kidney, urinary bladder & thyroid toxicant May cause serious damage to the eyes USEPA - some evidence to suggest possible human carcinogen |
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| 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 |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
No information available | |||
| CLP classification 2013 | - | |||
| EC Risk Classification |
N - Dangerous for the environment: R50/53 | |||
| EC Safety Classification |
- | |||
| WHO Classification | NL | - | Not listed | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | pyrasulfotole |
| French | - |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | pirasulfotol |
| Greek | - |
| Slovenian | - |
| Polish | - |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Sunday 01 April 2018
Contact: aeru@herts.ac.uk