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dimethenamid (Ref: SAN 582H)
** dimetenamid ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status 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: Click to access a note on the approvals information on this site

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: Click here for further information on the general chemical status information used on this site
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: Click here for further information on the general chemical status information used on this site
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 Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • BASF Corp
  • DuPont
  • King Tech
Example products using this active
  • Frontier
  • Leadoff
  • Optill
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 Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
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 Click here for a note on the limitations of the GUS 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 Click here for a note on the limitations of the SCI-GROW index Value 7.64 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Low
Maximum UV-vis absorption L mol-1 cm-1 - - -
Surface tension (mN m-1) - - -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
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 Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
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 Click here for further information on 1107/2009 relevancy
2-((2,4-dimethyl-3-thienyl)-((1S)-2-methoxy-1-methyl-ethyl)amino)-2-oxo-acetic acid This metabolite may cause environmental pollution, click here for further information Soil   0.102   Major fraction, Relevancy unknown
2-((2,4-dimethyl-3-thienyl)-((1S)-2-methoxy-1-methyl-ethyl)amino)-2-oxo-ethanesulfonic This metabolite may cause environmental pollution, click here for further information Soil   0.127   Major fraction, Relevancy unknown


ECOTOXICOLOGY

for dimethenamid

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
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 Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the 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 Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes No information available
CLP classification 2013 None allocated at this time
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22, R43
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II - Warning - Moderately toxic
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for dimethenamid

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