| dimethenamid (Ref: SAN 582H) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for dimethenamid
Description: A soil-applied herbicide used to control a variety of broad-leaved weeds and grasses
Example pests controlled: Black grass; Chickweed; Cleavers; Mayweed; Forget-me-not; Speedwell; Shepherd's purse; Cranes-bill
Example applications: Field corn; Oilseed rape; Soybeans; Vines
Efficacy & activity: -
Availability status: Unknown
Introduction & key dates: 1996
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Germany |
| 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 |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
Chemical structure:
| Isomerism | A chiral molecule, dimethenamid is an isomeric mixture of the M and P stereoisomers. Dimethenamid-P is the more biologically active isomer. |
| Chemical formula | C12H18ClNO2S |
| Canonical SMILES | CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | JLYFCTQDENRSOL-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3S |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |
| Substance group | Chloroacetamide | |
| Minimum active substance purity | - | |
| Known relevant impurities | - | |
| Substance origin | Synthetic | |
| Mode of action | Absorbed via roots, little translocation. Inhibition of mitosis and cell division. | |
| CAS RN | 87674-68-8 | |
| EC number | - | |
| CIPAC number | 654 | |
| US EPA chemical code | 129051 | |
| PubChem CID | 91744 | |
| Molecular mass (g mol-1) | 275.79 | |
| PIN (Preferred Identification Name) | rac-2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-[(2R)-1-methoxypropan-2-yl]acetamide | |
| IUPAC name | (RS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide | |
| CAS name | 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide | |
| Other status information | Chemical subject to PIC regulations | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | K3 | |
| Herbicide Resistance Classification (WSSA) | 15 | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | - | |
| Physical state | Yellow-brown viscous liquid | |
| Related substances & organisms | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
|
|||
| Example products using this active |
|
|||
| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | - | |||
ENVIRONMENTAL FATE
for dimethenamid
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 1200 | A4 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | Miscible | C4 - Acetone | - | |
| Miscible | C4 - Ethyl acetate | - | ||
| Miscible | C4 - Hexane | - | ||
| Miscible | C4 - Toluene | - | ||
| Melting point (oC) | - | - | - | |
| Boiling point (oC) | 127 | L2 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | 91 | L3 - (closed cup) | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.58 X 1002 | Calculated | - |
| Log P | 2.2 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.2 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.37 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 8.60 X 10-03 | A5 | Non-volatile | |
GUS leaching potential index  |
2.41 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 7.64 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 13 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 13 | A5 | Non-persistent | |
| DT50 (field) | 13 | A4 | Non-persistent | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 8-64 days, field studies DT50 range 3.2-34.7 days; Other sources: DT50 20 days (DW4) | |||
| 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 | 16.4 | A5 | Slow |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | - | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 0.88 | A5 | Mobile |
| Kfoc | 69 | |||
| 1/n | 0.961 | |||
| Notes and range | EU dossier kf range 0.32-1.6, Kfoc range 40-114 mL/g,1/n range 0.929-0.979, Soils=5 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 2-((2,4-dimethyl-3-thienyl)-((1S)-2-methoxy-1-methyl-ethyl)amino)-2-oxo-acetic acid |
Soil | 0.102 | Major fraction, Relevancy unknown | |
| 2-((2,4-dimethyl-3-thienyl)-((1S)-2-methoxy-1-methyl-ethyl)amino)-2-oxo-ethanesulfonic |
Soil | 0.127 | Major fraction, Relevancy unknown | |
ECOTOXICOLOGY
for dimethenamid
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | Low risk | A5 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 397 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 33.3 | A5 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | 1908 | A5 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 2.6 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 2.5 | A5 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 16 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 1.25 | F3 Daphnia magna, LOEC | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 4.8 | 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) | 0.028 | A5 Lemna gibba | Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.062 | L3 Scenedemus subspicatus | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 94 | A5 | Moderate |
| Oral acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 147 | A5 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 | - | - | - |
| % Effect | 100 | Mortality Dose: 1.0 kg ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 11 27 |
Mortality Fertility Dose: 1.0 kg ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 6.3 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for dimethenamid
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) | 397 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 4.99 | A5 Rat (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.02 | A5 Dog, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.25 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.04 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 10 | A5 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (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 | 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 |
No information available | |||
| CLP classification 2013 | None allocated at this time | |||
| EC Risk Classification |
Xn - Harmful: R22, R43 N - Dangerous for the environment: R50, R53 |
|||
| EC Safety Classification |
- | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | II | - | Warning - Moderately toxic | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | dimethenamid |
| French | dimethenamid |
| German | Dimethenamid |
| Danish | dimethenamid |
| Italian | dimetenamid |
| Spanish | dimetenamida |
| Greek | - |
| Slovenian | dimetenamid |
| Polish | dimetenamid |
| Swedish | - |
| Hungarian | dimethenamid |
| Dutch | - |
Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk