| dimethipin (Ref: N 252) |
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Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for dimethipin
Description: A plant growth regulator and defoliant used on a range of crops
Example pests controlled: Growth
Example applications: Potatoes; Cotton; Rubber trees; Nursery stock
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1974, first reported
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Greece |
| Date inclusion expires | Expired |
| EU Candidate for substitution (CfS) | - |
| 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 | - |
| Chemical formula | C6H10O4S2 |
| Canonical SMILES | CC1=C(S(=O)(=O)CCS1(=O)=O)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | PHVNLLCAQHGNKU-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C6H10O4S2/c1-5-6(2)12(9,10)4-3-11(5,7)8/h3-4H2,1-2H3 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide, Plant growth regulator | |||
| Substance group | Unclassified | |||
| Minimum active substance purity | 965 g/kg | |||
| Known relevant impurities | EU dossier - None declared | |||
| Substance origin | Synthetic | |||
| Mode of action | Interferes with protein synthesis in the plant epidermis, functions by stressing the plant’s stomatal system causing it to lose water and defoliate/desiccate. | |||
| CAS RN | 55290-64-7 | |||
| EC number | 259-572-7 | |||
| CIPAC number | 689 | |||
| US EPA chemical code | 118901 | |||
| PubChem CID | 41385 | |||
| Molecular mass (g mol-1) | 210.27 | |||
| PIN (Preferred Identification Name) | 5,6-dimethyl-2,3-dihydro-1gamma6,4gamma6-dithiine-1,1,4,4-tetrone | |||
| IUPAC name | 2,3-dihydro-5,6-dimethyl-1,4-dithiine 1,1,4,4-tetraoxide | |||
| CAS name | 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetraoxide | |||
| Other status information | - | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Z | |||
| 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 |
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 | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Often available as a suspension concentrate that is diluted with water and used as a spray. | |||
ENVIRONMENTAL FATE
for dimethipin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 1843 | A5 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 20 | A5 - Heptane | - | |
| 3600 | A5 - Xylene | - | ||
| 10000 | A5 - Methanol | - | ||
| 122000 | A5 - Acetone | - | ||
| Melting point (oC) | 168 | A5 | - | |
| Boiling point (oC) | - | - | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.76 X 10-01 | Calculated | - |
| Log P | -0.17 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.59 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 10.9 | A5 | - | |
| Note: Very weak acid | ||||
| Vapour pressure at 20oC (mPa) | 0.051 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.33 X 10-11 | A5 | Non-volatile | |
GUS leaching potential index  |
8.79 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 3.55 X 10+02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | No maxima detected | A3 | - | |
| Surface tension (mN m-1) | 68.7 | A5 at 20oC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 183 | A3 | Persistent |
| DT50 (lab at 20oC) | 431 | A5 | Very persistent | |
| DT50 (field) | 183 | A5 | Persistent | |
| DT90 (lab at 20oC) | 1025 | A5 | - | |
| DT90 (field) | 932 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossiers lab studies DT50 range 157-673 days, DT90 range 521-2236 days, field studies 2 soils DT50 range 168-198 days USA, DT90 range 658-1206 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 | 330 | A5 | Stable |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable at pH 5 to pH 9 at 22 degC | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | 470 | A5 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | A5 | Very mobile |
| Koc | 2.0 | |||
| Notes and range | EU dossier Koc range 1.0 (sand/loam) - 3.2 (clay) mL/g; Other sources: 10 mL/g (DW3) | |||
| Freundlich | Kf | 0.12 | R4 | Very mobile |
| Kfoc | 4.6 | |||
| 1/n | 1.02 | |||
| Notes and range | 2 USA/Canadian soils. Kf range 0.04-0.2, Kfoc range 2.7-7.1, 1/n range1.02-1.03, Soils=2 | |||
| pH sensitivity | No | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| cysteinyl-glycine | - | Rat (Urinary) | - | - |
| - | N-acetyl-cysteinyl conjugates | Rat (Urinary) | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 4.3 | A5 | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 458 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 2 | L2 Rat, 2 year | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | 896 | A5 Anas platyrhynchos | Moderate | |
| Birds - Short term dietary (LC50/LD50) | 1173 mg kg bw-1 day-1 | A5 Anas platyrhynchos | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 52.8 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 3.3 | A5 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 29.9 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.61 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 11.8 | F3 Americamysis bahia | Moderate | |
| 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) | 2.1 | A5 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 22 | A5 Scenedemus subspicatus | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | - | - | - |
| Oral acute 48 hour LD50 (μg bee-1) | 64.7 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 102 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 2.17 | A5 Eisenia foetida, 56 days | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 3750 | >, as mL product ha-1 (Havade 25F: Conc 250 g/L) A5 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 2398 | as mL product ha-1 (Havade 25F: Conc 250 g/L) A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: Chronic effect Biopolymer degradation: Chronic effect |
A4 Dose: Not stated, 63 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for dimethipin
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) | 458 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.88 | A5 Rat (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.009 | A2, SF=200 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A5 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.031 | A2 Rat, 90 day, SF=100 | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | No unacceptable risks to bystanders identified Negligible risk of dietary exposure |
||
| Occupational | Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment | |||
| 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; Calc MAC=27.0 μg l-1; A5 | - | |
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 | USEPA - possible human carcinogen | |||||||
: 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 oxidising or explosive IMDG Transport Code is usually 6.1 |
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| CLP classification 2013 | - | |||
| EC Risk Classification |
Carcinogen category 3: R40 T - Toxic: R23 Xn - Harmful: R22, R43 Xi - Irritant: R36 |
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| EC Safety Classification |
S1/2, S13, S25, S36, S37, S45, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | I, III | - | Danger - Highly toxic, Caution - Slightly toxic | |
| UN Number | Usualy 2811 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | dimethipin |
| French | dimethipin |
| German | Dimethipin |
| Danish | dimethipin |
| Italian | dimetipin |
| Spanish | dimetipin |
| Greek | - |
| Slovenian | dimetipin |
| Polish | dimetypina |
| Swedish | - |
| Hungarian | dimethipin |
| Dutch | - |
Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk