Lexikon
Sulcotrione is a foliar herbicide. Its mode of action is the Inhibition of 4-hydroxyphenyl-pyruvate-dioxygenase (4-HPPD).
Common name (ISO): Sulcotrione
Chemical name (IUPAC): 2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione
Chemical name (CA): 1,3-cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-benzoyl]-
CIPAC No: 723; CAS No: 99105-77-8;
Minimum purity: 950 g/kg (on a dry weight basis)
Molecular formula:: C14 H13 Cl O5 S
Identity of relevant impurities (of toxicological, ecotoxicological and/or environmental concern)
Hydrogen cyanide: maximum content 80 mg/kg on a dry weight basis
Toluene: maximum content 4 g/kg on a dry weight basis.
Molecular mass: 328.77 g/mol
The Standing Committee of the EUROPEAN COMMISSION HEALTH AND CONSUMERS DIRECTORATE-GENERAL on the Food Chain and Animal Health at its meeting on 28 October 2008 decidedon the inclusion of sulcotrione in Annex I of Directive 91/414/EEC (the placing of plant protection products on the market).
The following reference values have been finalised as part of the re-evaluation:
ADI: 0.0004 mg/kg bw/day
ARfD: not allocated, not necessary
AOEL: 0.0006 mg/kg bw/day.
Complete characterisation:
General status:
Pesticide Type | Herbicide |
Chemical Group | Triketone |
Substance origin | Synthetic |
Mode of Action | Absorbed mainly by the leaves but also some root uptake. 4-HPPD inhibitor. |
CAS RN | 99105-77-8 |
EC Number | - |
CIPAC Number | 723 |
US EPA Chemical code | - |
Chemical Formula | C14H13ClO5S |
SMILES | O=C(c1ccc(cc1Cl)S(=O)(=O)C)C2C(=O)CCCC2=O |
International Chemical Identifier (InChI) | InChI=1/C14H13ClO5S/c1-21(19,20)8-5-6-9(10(15)7-8)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3 |
Structure diagram available? | Yes |
Molecular Mass (g mol-1) | 328.77 |
IUPAC Name | 2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione |
CAS Name | 2-[2-chloro-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione |
Other status information | - |
Herbicide Resistance (HRAC) Classification | F2 |
Insecticide Resistance (IRAC) Classification | Not applicable |
Fungicide Resistance (FRAC) Classification | Not applicable |
Physical State | White solid |
ENVIRONMENTAL FATE
Property | Value | Source/Quality Score/Other Information | Interpretation | |
Solubility - In water at 20oC (mg l-1) | 1670 | A4 | High | |
Solubility - In organic solvents at 20oC (mg l-1) | 2000 | A5 - Xylene | - | |
190000 | A5 - Dichloromethane | - | ||
48000 | A5 - Acetone | - | ||
300 | A5 - 1-Octanol | - | ||
Melting Point (oC) | 139 | A5 | - | |
Boiling Point (oC) | Decomposes before boiling | A5 | - | |
Degradation point (oC) | 170 | A5 | - | |
Flashpoint (oC) | Not highly flammable | A5 | - | |
Octanol-water partition coefficient at pH 7, 20oC | P | 2.00 X 10-02 | Calculated | - |
Log P | -1.7 | A5 | Low | |
Bulk density (g ml-1)/Specific gravity | - | - | - | |
Dissociation constant (pKa) at 25oC | 3.13 | A5 | - | |
Note: Weak acid | ||||
Vapour pressure at 25oC (mPa) | 5.00 X 10-03 | A5 | Volatile | |
Henry's law constant at 25oC (Pa m3 mol-1) | 6.0 X 10-07 | A5 | Non-volatile | |
Henry's law constant at 20oC (dimensionless) | 4.33 X 10-09 | Q2 | Non-volatile | |
GUS leaching potential index | 3.42 | Calculated | High leachability | |
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate | Value | 4.02 X 10-01 | Calculated | - |
Note | - | |||
Potential for particle bound transport index | - | Calculated | Low | |
Maximum UV-vis absorption L mol-1 cm-1 |
285nm = 15239, 283.5nm = 16868, 259 nm = 20364 | A5 | - | |
Surface tension (mN m-1) | 69.0 | A5 at 20oC, 90% solution | - |
Degradation:
Property | Value | Source/Quality Score/Other Information | Interpretation | |
Soil degradation (days) (aerobic) | DT50 (typical) | 25 | A5 | Non-persistent |
DT50 (lab at 20oC) | 25.3 | A5 | Non-persistent | |
DT50 (field) | 3.6 | A5 | Non-persistent | |
DT90 (lab at 20oC) | 100.2 | A5 | - | |
DT90 (field) | 18.4 | A5 | - | |
Note | EU dossier lab studies DT50 range 10.8-89.7 days, DT90 range 47-246 days; field studies DT50 range 1.2-11.4 days, DT90 range 6.9-38 days | |||
Aqueous photolysis DT50 (days) at pH 7 | Value | 25.6 | A5 | Slow |
Note | pH sensitive: DT50 13 days at pH 4, 40.9 days at pH 9, all data for 5 cm depth and seasonal mean values. Degradation slower at 30 cm depth. | |||
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | Very persistent |
Note | Stable at pH 5 to pH 9, temp 25-40 Deg C | |||
Water-Sediment DT50 (days) | 63.9 | A5 | Moderately fast | |
Water phase only DT50 (days) | 9.5 | A5 | Moderately fast |
Soil adsorption and mobility:
Property | Value | Source/Quality Score/Other Information | Interpretation | |
Linear | Kd | - | - | - |
Koc | - | |||
Notes and range | - | |||
Freundlich | Kf | 1.05 | A5 | Mobile |
Kfoc | 36 | |||
1/n | 0.839 | |||
Notes and range | EU dossier Kf range 0.29-2.26, Kfoc range 17-58 mL/g, 1/n range 0.812-0.888, Soils=6 | |||
pH sensitivity | Predominantly OC-dependent but pH-dependent to a minor extent |
Key metabolites:
Metabolite | Formation Medium | Estimated Maximum Occurrence Fraction | 91/414 Relevancy | |
2-chloro-4-methylsulfonyl-benzoic acid | Soil | 0.603 | Major fraction, Relevant |
Other known metabolites:
Metabolite name and reference | Aliases | Formation Medium / Rate | Estimated Maximum Occurrence Fraction | Metabolising Enzymes |
4-hydroxyphenyl pyruvate | - | Rat (Blood) | - | - |
4-hydroxy-sulcotrione, 2-[2-chloro-4-(methylsulfonyl)benzoyl]-4-hydroxycyclohexane-1,3-dione | sulcotrione metabolite M02 | Rat (Urinary) | - | - |
5-hydroxy-sulcotrione, 2-[2-chloro-4-(methylsulfonyl)benzoyl]-5-hydroxycyclohexane-1,3-dione | sulcotrione metabolite M04 | Rat (Urinary) | - | - |
ECOTOXICOLOGY
Property | Value | Source/Quality Score/Other Information | Interpretation | |
Bio-concentration factor | BCF | - | - | - |
CT50 (days) | - | - | ||
Bioaccumulation potential | - | Calculated | Low | |
Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
Mammals - Short term dietary NOEL | (mg kg-1) | > 0.5 | L2 Rat, 2 year | High |
(ppm diet) | > 100 | - | ||
Birds - Acute LD50 (mg kg-1) | > 1350 | A5 Anas platyrhynchos | Moderate | |
Birds - Short term dietary (LC50/LD50) | > 1259 mg kg bw-1 day-1 | A5 Anas platyrhynchos | - | |
Fish - Acute 96 hour LC50 (mg l-1) | 227 | A5 Oncorhynchus mykiss | Low | |
Fish - Chronic 21 day NOEC (mg l-1) | 3.2 | A4 Oncorhynchus mykiss, Juvenile growth | - | |
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 848 | A5 Daphnia magna | Low | |
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | > 75 | A5 Daphnia magna | - | |
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) | 0.051 | A5 Lemna gibba | Moderate | |
Algae - Acute 72 hour EC50, growth (mg l-1) | 1.2 | A5 Raphidocelis subcapitata | Moderate | |
Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
Honeybees - Acute 48 hour LD50 (µg bee-1) | 50 | A5 Oral | Moderate | |
Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 | Moderate | |
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
Other soil macro-organisms - e.g. Collembola | LR50product ha EC50product ha NOECproduct ha % Effect |
- | - | - |
Other arthropod (1) | LR50 g ha-1 | 450 | 48 hour A5 Aphidius rhopalosiphi, adult |
Moderately harmful at 1 kg ha-1 |
% Effect | - | - | - | |
Other arthropod (2) | LR50 g ha-1 | 450 | 7 day A5 Typhlodromus pyri |
Moderately harmful at 1 kg ha-1 |
% Effect | - | - | - | |
Soil micro-organisms | Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect |
A5 Dose: 4.5 kg/ha, 28 days |
- | |
Mesocosm study data | NOEAEC mg l-1 | - | - | - |
NOEAEC mg l-1 | - | - | - |
HUMAN HEALTH AND PROTECTION
General:
Property | Value | Source/Quality Score/Other Information | Interpretation | |
Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
Mammals - Dermal LD50 (mg kg-1 body weight) | > 4000 | A5 Rat | - | |
Mammals - Inhalation LC50 (mg l-1) | > 1.63 | A5 Rat, 4hr (nose only) | - | |
Other Mammal toxicity endpoints | - | - | ||
ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.0004 | A5 Rat, SF=100 | - | |
ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A5 | - | |
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.0006 | A5 Rat, SF=100 | - | |
Dermal penetration studies (%) | 0.1-0.5 | A5 concentration dependant | - | |
Dangerous Substances Directive 76/464 | - | - | - | |
Exposure Limits | - | - | - | |
Exposure Routes | Public | [No unacceptable risks to bystanders identified for intended use] | ||
Occupational | [No unacceptable risks to operators or other workers identified for intended use] | |||
Examples of European MRLs (mg kg-1) | Value | Maize: 0.05 | ||
Note | [A5 EU dossier proposals] For the EU pesticides database click here |
|||
Drinking Water MAC (µg l-1) | - | - | - |
Health issues: skin sensitiser, potential kidney and liver toxicant, may cause eye damage
Handling issues:
Property | Value | Source/Quality Score/Other Information | Interpretation | ||||
General <="" font="" border="0"> | [Not explosive or oxidising] | ||||||
EC Risk Classification <="" font="" border="0"> | [Reproduction risk category 3: R63], [Xi - Irritant: R43] | ||||||
EC Safety Classification <="" font="" border="0"> | - | ||||||
WHO Classification | NL | - | Not listed | ||||
US EPA Classification (formulation) | No consensus across products or no products available | - | - | ||||
UN Number | - | ||||||
Waste disposal & packaging <="" font="" border="0"> | - |
Sources:
http://sitem.herts.ac.uk/aeru/iupac/Reports/600.htm
http://ec.europa.eu/food/plant/protection/evaluation/existactive/list_sulcotrione.pdf
http://compendium.bayercropscience.com/BAYER/CropScience/CropCompendium/BCSCropComp.nsf/id/sulcotrione.htm#
"surface water status" is the general expression of the status of a body of surface water, determined by the poorer of its ecological status and its chemical status.
"ecological status" is an expression of the quality of the structure and functioning of aquatic ecosystems associated with surface waters, classified in accordance with Annex V. of the Water Framework Directive (WFD), 60/2000/EC
"good surface water chemical status" means the chemical status required to meet the environmental objectives for surface waters established in Article 4(1)(a) of WFD (60/2000/EC) that is the chemical status achieved by a body of surface water in which concentrations of pollutants do not exceed the environmental quality standards established in Annex IX and under Article 16(7), and under other relevant Community legislation setting environmental quality standards at Community level.
"good ecological potential" is the status of a heavily modified or an artificial body of water, so classified in accordance with the relevant provisions of Annex V. of Water Framework Directive (WFD), (60/2000/EC).
"good ecological status" is the status of a body of surface water, so classified in accordance with Annex V. of WFD (Water Framework Directive), 60/2000/EC
Surfactant Enhanced Aquifer Remediation (SEAR), in its most basic form, could thus be considered a chemical enhancement to pump and treat. A chemical solution is pumped across a contaminated zone by introduction at an injection point and removal from an extraction point. To cover the entire contaminated zone, a number of injection and extraction wells are used; the well configuration is determined by the subsurface distribution of NAPL and the hydrogeologic properties of the aquifer.
SEAR is a source zone remediation technology. SEAR removes the residual phase contamination from which the dissolved phase plume is derived. Free phase contamination is typically removed by conventional pumping before SEAR is employed. SEAR does not have an immediate effect on the dissolved phase plume concentrations and is not a dissolved phase plume remediation technology. Removal of the source does however cause an intermediate and long-term reduction in dissolved phase contaminant concentrations.
Surfactants are unique chemical agents that greatly enhance the solubility of organic contaminants in aqueous media. They are also able to reduce the interfacial tension (IFT - that force existing where two fluids meet that keeps them as separate fluids) between the aqueous and organic phases to mobilize the organic phase. To illustrate the two mechanisms, we can use the familiar examples of the cleaning action of household cleaning detergents, which contain surfactants as a common constituent. We have witnessed surfactant-induced solubilization in the oily solution resulting from soaking oily pots and pans in dish detergent; we have observed a reduction in IFT from oil droplets or a sheen of oil coming off the pan due to the presence of a detergent. A surfactant flood can be designed to remove contaminants either primarily by solubilization or primarily by mobilization. Surfactant mobilization can remove more DNAPL in less time; however, there is greater risk of uncontrolled downward movement of DNAPL, as DNAPL is being physically displaced by the surfactant solution. Thus, to conduct a mobilization flood, it is necessary to have an aquitard as a barrier to prevent vertical DNAPL migration. It is important to identify from the outset whether solubilization or mobilization of DNAPL is desired, because not all surfactants can be used to conduct a mobilization flood.
The primary objective in SEAR design is to remove the maximum amount of contaminant with a minimum amount of chemicals and in minimal time while maintaining hydraulic control over the injected chemicals and contaminant. Each step in the design process must keep this in mind. Design challenges include precisely locating the DNAPL, finding the optimum surfactant solution for a given DNAPL composition and soil type, and fully characterizing the hydraulic properties of the aquifer, particularly the heterogeneities typically present in the subsurface environment. Because it is impossible to know with certainty the variations in aquifer properties over the treatment zone, numerical modeling tools are used to simulate how the system may respond in the presence of these unknown factors. Numerical modeling is also necessary to understand the dynamics of the flooding process under the hydrogeologic conditions at the site. SEAR has been acknowledged to be a promising, innovative technology for the removal of DNAPLs primarily because of the history of the use of surfactant-enhanced oil recovery by the petroleum industry.
Source: http://www.cpge.utexas.edu/ee/sear.html
a systematic collection of information or data. A survey can be conducted to collect information from a group of people or from the environment. Surveys of a group of people can be conducted by telephone, by mail, or in person. Some surveys are done by interviewing a group of special people.
Environmental survey is data collection about an area, a catchment, about ecosystems and ecosystem members, about contamination at a site or the integrated collection of many different information.
Streghts, Weeknesses, Opportunities, Threats. Methodology for descriptive evaluation of new technologies, processes, methods, projects or businesses. It is a strategic planning method used to evaluate the Strengths, Weaknesses, Opportunities, and Threats involved in a project or business. It involves specifying the objective of the business venture or project and identifying the internal and external factors that are favourable and unfavourable to achieving that objective.
the group or recognizable pattern of symptoms or abnormalities that indicate a particular trait or disease.
a biologic response to multiple substances where one substance worsens the effect of another substance. The combined effect of the substances acting together is greater than the sum of the effects of the substances acting by themselves.
See also additive effect and antagonistic effect.