| carboxin (Ref: D 735) |
 |
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SUMMARY
Carboxin is an effective agricultural fungicide that is approved for use in the EU subject to Member State approval. It is moderately soluble in water, is non-volatile and, based on its chemical properties, would not normally be expected to leach to groundwater. It tends not to persist in soil or water systems. Whilst it is an irritant, its mammalian toxicity is low and no significant health effects have been identified. It shows a low or moderate ecotoxicity to most species. GENERAL INFORMATION 
for carboxin
Description: An anilide fungicide for bunts and smuts normally that is normally used as a seed treatment
Example pests controlled: Smut; Rots; Bunt; Blight; Leaf stripe; Net blotch
Example applications: Rice; Vegetables; Corn; Wheat; Barley; Oats; Turf grass; Cotton
Efficacy & activity: Carboxin has been shown to be an effective fungicide via field trials and long use globally.
Availability status: Current
Introduction & key dates: 1966, first reported; 1969, first introduced
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | UK |
| Date inclusion expires | 31/05/2021 |
| EU Candidate for substitution (CfS) | No |
| 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: Australia, USA
Chemical structure:
| Isomerism | None |
| Chemical formula | C12H13NO2S |
| Canonical SMILES | CC1=C(SCCO1)C(=O)NC2=CC=CC=C2 |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | GYSSRZJIHXQEHQ-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14) |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide | |
| Substance group | Oxathiin | |
| Minimum active substance purity | 970 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Synthetic | |
| Mode of action | Systemic, inhibits mitochondrial function. Succinate Dehydrogenase Inhibitor. | |
| CAS RN | 5234-68-4 | |
| EC number | 226-031-1 | |
| CIPAC number | 273 | |
| US EPA chemical code | 090201 | |
| PubChem CID | 21307 | |
| Molecular mass (g mol-1) | 235.30 | |
| PIN (Preferred Identification Name) | 2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide | |
| IUPAC name | 5,6-dihydro-2-methyl-1,4-oxathiine-3-carboxanilide | |
| CAS name | 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | 7 | |
| Examples of recorded resistance | - | |
| Physical state | Colourless crystals | |
| 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 | None | |||
| Formulation and application details | Usually formulated as a flowable concentrate that is diluted with water for use as a seed treament. | |||
ENVIRONMENTAL FATE
for carboxin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 134 | A5 | Moderate | |
| Solubility - In organic solvents at 20oC (mg l-1) | 220000 | A5 - Acetone | - | |
| 110000 | A5 - Ethyl acetate | - | ||
| 89000 | A5 - Methanol | - | ||
| 53000 | A5 - Toluene | - | ||
| Melting point (oC) | 91.5 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 210 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.00 X 1002 | Calculated | - |
| Log P | 2.3 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.36 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 0.5 | A5 | - | |
| Note: Strong acid | ||||
| Vapour pressure at 20oC (mPa) | 0.02 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 3.20 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
-2.15 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.15 X 10-03 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | 205nm = 17443, 295nm = 6585 | A5 | - | |
| Surface tension (mN m-1) | 61.2 | A5 at 20oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 0.5 |
A5 | Non-persistent |
| DT50 (lab at 20oC) | 0.28 | A5 | Non-persistent | |
| DT50 (field) | 3.3 | A5 | Non-persistent | |
| DT90 (lab at 20oC) | 1.99 | A5 | - | |
| DT90 (field) | 11.1 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier Lab studies DT50 range 0.07-1.68 days, DT90 range 0.23-3.49 days; field studies DT50 range 0.27-11 days, DT90 range 0.9-37 days; Other sources: DT50 1 day (R3) | |||
| 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 | 0.1 | A5 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable between pH 4 and pH 9 | |||
| Water-sediment DT50 (days) | 17.3 | A5 | Fast | |
| Water phase only DT50 (days) | 13.6 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 1.3 | A5 | Moderately mobile |
| Koc | 99.4 | |||
| Notes and range | EU dossier Kd range 1.03-1.78 mL/g, Koc range 81-124 mL/g, Soils=5 | |||
| Freundlich | Kf | 1.95 | A5 | Very mobile |
| Kfoc | 1.3 | |||
| 1/n | 0.80 | |||
| Notes and range | EU dossier Kf range 1.56-2.71 mL/g, Kfoc range 123-213 mL/g, 1/n range 0.79-0.81, Soils=5 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| carboxin sulfoxide |
Soil | 0.782 | Major fraction, Relevant | |
| oxycarboxin (Ref: F 461) |
Soil | 0.170 | Major, Relevant | |
| oxathiine amide sulfoxide |
Soil | 0.274 | Major fraction, Relevant | |
| oxathiine amide sulfone |
Soil | 0.145 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| acetanilide | - | Plant | - | - |
| 4-hydroxycarboxin sulfone | carboxin Rat M03 | Rat (Urine & Bile) | - | - |
| 4-O-glucuronyl-2-hydroxycarboxin | carboxin Rat M04 | Rat (Urine) | - | - |
| 4-hydroxycarboxin | carboxin Rat M07 | Rat (Urine, Faeces & Bile) | - | - |
| monomethoxy dihydroxycarboxin | carboxin Rat M09 | Rat (Urine & Faeces) | - | - |
| 2-methoxycarboxin sulfoxide-4-glucuronide | carboxin Rat M11 | Rat (Bile & Urine) | - | - |
| 4-O-glucuronyl carboxin | carboxin Rat M12 | Rat (Bile) | - | - |
| - | - | - | - | - |
| 2-[2-anilino-2-oxoacetyl)thio]ethyl acetate | - | Soil; Water; Groundwater | - | - |
| 2-hydroxy-2-methyl-N-phenyl-1,4-oxathiane-3-carboxamide-4-oxide | hydrated carbon sulfoxide; carboxin M09 | Soil; Water; Groundwater | - | - |
| 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid-4-oxide | PH-3; alpha-vinylsulfinyl acetanilide; P/V-05; M234 | Soil; Water; Groundwater | - | - |
| 4-O-glucuronyl carboxin sulfoxide | carboxin Rat M01 | Rat (Urine & Bile) | - | - |
| 4-hydroxycarboxin sulfoxide | carboxin Rat M02 | Rat (Urine & Bile) | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 13 | Q2 Estimated | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 2588 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 5.5 | A5 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2150 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5000 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 2.3 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.32 | A5 Cyprinidae | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 57 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.32 | A4 Daphnia magna, 17 day | 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) | 0.92 | L3 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.48 | A5 Pseudokirchneriella subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 250 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 50 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | 0 | A4 Folsomia candida, % Mortality [Dose: <1g carboxin sulfone/kg soil] | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 0 -21.5 |
Mortality Reproduction Dose: 776 mg carboxin + 770 mg thiram/kg seed A5 Aleochara bilineata, adult/juvenile |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 660 g ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for carboxin
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) | 2588 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 4000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 4.7 | A5 Rat, 4 hr | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.008 | A3 Rat, 2 year, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A4 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.055 | A3 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 3.3-5.0 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Negligible risk to the public due to pattern of use | ||
| Occupational | Acceptable risks with PPE/PPC | |||
| 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=4.8 μg l-1 | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Mild skin sensitiser Possible kidney toxicant |
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: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Not explosive or oxidising | |||
| CLP classification 2013 | Health: H302 | |||
| EC Risk Classification |
Carcinogen category 3: R40 Xn - Harmful: R43 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S36/37, S60, S61 | |||
| WHO Classification | III | - | Slightly hazardous | |
| US EPA Classification (formulation) | III | - | Caution - Slightly toxic | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | carboxin |
| French | carboxine |
| German | Carboxin |
| Danish | carboxin |
| Italian | carbossina |
| Spanish | carboxina |
| Greek | carboxin |
| Slovenian | karboksin |
| Polish | karboksyna |
| Swedish | karboxin |
| Hungarian | karboxin |
| Dutch | carboxin |
Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk