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dimethenamid-P
** dimethenamide-P ** (S)-dimethenamid ** 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-P

Description: A pre-emergence herbicide often used to control annual grasses, annual broad-leaved weeds and sedges

Example pests controlled: Black grass; Chickweed; Cleavers; Mayweed; Forget-me-not; Speedwell; Shepherd's purse; Cranes-bill

Example applications: Soybeans; Vegetables including beans, onions, cabbage; Peanuts; Grapevines; Ornamentals; Sugarbeet; Sunflowers; Stone fruit

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1999, USA; 2000, UK

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Germany/Bulgaria
Date inclusion expires 31/08/2034
EU Candidate for substitution (CfS) No
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

Also used in: Australia

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism Dimethenamid-P is the more biologically active isomer of chiral dimethenamid and is used at lower rates.
Chemical formula C12H18ClNO2S
Canonical SMILES CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C
Isomeric SMILES CC1=CSC(=C1N([C@@H](C)COC)C(=O)CCl)C
International Chemical Identifier key (InChIKey) JLYFCTQDENRSOL-VIFPVBQESA-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,5-6H2,1-4H3/t9-/m0/s1
2D 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 930 g/kg
Known relevant impurities EU dossier - 1,1,1,2-tetrachloroethane <1.0 g/kg; 2,4-dimethylthiopene-3-ol <=1.5 g/kg
Substance origin Synthetic
Mode of action Selective, fatty acid inhibitor
CAS RN 163515-14-8
EC number -
CIPAC number 638
US EPA chemical code 129501
PubChem CID 13633097
Molecular mass (g mol-1) 275.8
PIN (Preferred Identification Name) 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-[(2S)-1-methoxypropan-2-yl]acetamide
IUPAC name (S)-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-[(1S)-2-methoxy-1-methylethyl]acetamide
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) K3
Herbicide Resistance Classification (WSSA) -
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
Example products using this active
  • Elk
  • Shadow
  • Springbok
  • Frontier X-2
UK LERAP status None
Formulation and application details -


ENVIRONMENTAL FATE

for dimethenamid-P

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) 1499 A5 High
Solubility - In organic solvents at 20oC (mg l-1) 310000 A5 - n-Hexane -
310000 A5 - n-Heptane -
1000000 A5 - Toluene -
1000000 A5 - Acetone -
Melting point (oC) Solidification below -50 A5 -
Boiling point (oC) 280 A5 -
Degradation point (oC) 101 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 7.76 X 1001 Calculated -
Log P 1.89 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) 2.51 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 4.80 X 10-04 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.39 Calculated Low leachability
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 1.02 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 236nm = 7560 A5 -
Surface tension (mN m-1) 52.0 A5 at 20 degC, 0.1% w/ww -

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) 11 A5 Non-persistent
DT50 (lab at 20oC) 23 A5 Non-persistent
DT50 (field) 7 A5 Non-persistent
DT90 (lab at 20oC) 65 A5 -
DT90 (field) 42.2 A5 -
DT50 modelling endpoint - - -
Note EU dossier Lab studies DT50 range 8-67 days, DT90 range 26-104 days, field studies DT50 range 1.6-16 days, DT90 range 10.7-115.2 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 13.7 A5 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 9 over 30 days, 25 degC
Water-sediment DT50 (days) 28 A5 Fast
Water phase only DT50 (days) 24 A5 Slow

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 3.69 A5 Moderately mobile
Kfoc 227
1/n 1.0
Notes and range EU dossier Kf range 1.23-13.5 mL/g, Kfoc range 90-474 mL/g, 1/n range 0.92 -1.07, Soils=10
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   0.122   Major fraction, Relevant
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   0.133   Major fraction, Relevant
2-(2-((2,4-dimethyl-3-thienyl)-((1S)-2-methoxy-1-methyl-ethyl)amino)-2-oxo-ethylsulfinylacetic acid This metabolite may cause environmental pollution, click here for further information Soil   0.103   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
N-(2,4-dimethyl-3-thienyl)-N-(2-hydroxy-1-methylethyl)-2-(methylsulfinyl)acetamide Metabolite M02 Rat - -
N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide Metabolite M03; dechlorinated dimethanamid Sediment; Water - -
2-chloro-N-(2,4-dimethyl-3-thienyl)- N-(2-hydroxy-1-methylethyl)acetamide Metabolite M07 - - -
3,4-dihydro-4-(2,4-dimethyl-3-thienyl)-5-methyl-2H-1,4-oxazin-3-one Metabolite M08 - - -
4-(2,4-dimethyl-3-thienyl)-5-methyl-3-morpholinone Metabolite M09 - - -
N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)-2-(methylsulfonyl)acetamide Metabolite M10 Rat - -
N-(2,4-dimethyl-3-thienyl)-2-hydroxy-N-(2-methoxy-1-methylethyl)acetamide Metabolite M11 - - -
N-(2,4-dimethyl-3-thienyl)-N-(2-hydroxy-1-methylethyl)acetamide Metabolite M12 - - -
N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)-2-(methylsulfinyl)acetamide Metabolite M13 Rat - -
N-(2,4-dimethyl-3-thienyl)-N-(2-hydroxy-1-methylethyl)-2-(methylsulfonyl)acetamide Metabolite M14 Rat - -
4-(2,4-dimethyl-3-thienyl)-6-hydroxy-5-methyl-3-morpholinone Metabolite M15 Rat - -
sulfoxide of 2-[N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)amino]-2-oxoethyl-N-malonyl cysteine Metabolite M29 Rat - -
2-[N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)amino]-2-oxoethyl thioglycolic acid Metabolite M32 Rat - -
sulfoxide of 2-[N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)amino]-2-oxoethyl thiolactic acid Metabolite M30 Rat - -
N-(2-hydroxymethyl-4-methyl-3-thienyl)-N-(2-methoxy-1-methylethyl)-2-(methylsulfinyl)acetamide Metabolite M16 Rat - -
N-acetyl-S-(2-(N'-(2,4-dimethyl-3-thienyl)-N'-(2-methoxy-1-methylethyl)amino)-2-oxoethyl)cysteine mercapturate conj; Metabolite M17 Rat - -
methylated N-(2,4-dimethyl-3-thienyl-N-(2-methoxy-2-methylthio-acetyl)alanine Metabolite M18 Rat - -
methylated N-(2,4-dimethyl-3-thienyl)-N-((methylsulfonyl)acetyl)alanine Metabolite M19 Rat - -
1,5-dihydro-1-(2-methoxy-1-methylethyl)- 8-methylthieno-[thieno-[3,4-f][4,1]oxazepin-2(3H)-one Metabolite M20 Rat - -
4-(2,4-dimethyl-3-thienyl)-6-hydroxy-5-methyl-3-thiomorpholinone Metabolite M21 Rat - -
2,2'-dithiobis(N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide) Metabolite M22 Rat - -
2-[N-(2,4-dimethyl-3-thienyl)-N- (2-methoxy-1-methylethyl)amino]-2-oxoethyl-glutathione glutathione conj; Metabolite M24 Rat - -
2-[N-(2,4-dimethyl-3-thienyl)-N- (2-methoxy-1-methylethyl)amino]-2-oxoethyl-cysteine Metabolite M25 Rat; Plant - -
2-[N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)amino]-2-oxoethyl-thiolactic acid thiolactic acid conj; Metabolite M26 Rat; Plant - -
sulfoxide of 2-[N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)amino]-2-oxoethyl cysteine Metabolite M28 Rat - -


ECOTOXICOLOGY

for dimethenamid-P

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) 429 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) 1068 A5 Colinus virginianus Moderate
Birds - Short term dietary (LC50/LD50) > 5620 ppm A5 Colinus virginianus -
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) 3.2 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 1.25 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 2.7 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) 0.0060 A5 Lemna gibba High
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.019 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees (Apis spp.) Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 200 A5 Apis mellifera Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) 118.4 A4 Apis mellifera Low
Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) - - -
Bumblebees (Bombus spp.) Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) 200 A5 Bombus terrestris, 48hr Low
-
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 158 A5 Bombus terrestris, 48hr Low
-
Mason bees (Osmia spp.) Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) - - -
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) - - -
Other pollinators (1) Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) - - -
Mode of exposure -
Other pollinators (2) Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) - - -
Mode of exposure -
Earthworms - Acute 14 day LC50 (mg kg-1) 294.4 A5 Eisenia foetida Moderate
Earthworms - Chronic NOEC, reproduction (mg kg-1) 25.4 A5 Eisenia foetida Moderate
Other soil macro-organisms Acute LC50 (mg kg-1) - - -
Chronic NOEC (mg kg-1) 12.5 A5 Folsomia candida -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 0
46
Mortality
Fertility
Dose: 1.0 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 11
27
Mortality
Fertility
Dose: 1.0 kg ha-1
A5 Typhlodromus pyri, adult
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 4.93 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for dimethenamid-P

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) 429 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.16 A5 Rat, 4 hr (head/nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.02 A5 -
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) 0.1 A5 -
Dermal penetration studies (%) 10 A5 -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public No unacceptable risks to bystanders identified
Occupational Acceptable for intended uses
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A0; B0; C0; D0; E3

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

General human health issues Possible liver toxicant
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: 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 Prevent generation of mists
Not explosive or oxidising
CLP classification 2013 Health: H302, H317
Environment: H400
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R20/22, R42/43
EC Safety Classification Click here to view information omn the EU safety phrases S23, S36/37, S45
WHO Classification NL - Not listed
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for dimethenamid-P

Language Name
English dimethenamid-P
French dimethenamid-P
German Dimethenamid-P
Danish dimethenamid-P
Italian dimetenamid-P
Spanish dimetenamida-P
Greek -
Slovenian dimetenamid-P
Polish dimetenamid-P
Swedish -
Hungarian dimethenamid-P
Dutch dimethenamide-P

Record last updated: Monday 04 November 2019
Contact: aeru@herts.ac.uk