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pethoxamid (Ref: ASU 96 520H)
** pethoxamide ** TKC 94 ** Translations

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GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for pethoxamid

Description: A pre-emergence and early post-emergence herbicide to control some grass and broad-leaved weeds

Example pests controlled: Foxtail; Crabgrass; Barnyardgass; Ladysthumb; Bindweed; Pigweed; Common lambsquarter

Example applications: Corn; Winter OSR; Soybeans; Peas and beans; Tobacco

Efficacy & activity: Substances has been evaulated via field trials and has been in usefor many years

Availability status: Current

Introduction & key dates: 2002

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Austria/Czech Republic
Date inclusion expires 31/01/2019
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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C16H22ClNO2
Canonical SMILES CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) CSWIKHNSBZVWNQ-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C16H22ClNO2/c1-4-20-11-10-18(15(19)12-17)16(13(2)3)14-8-6-5-7-9-14/h5-9H,4,10-12H2,1-3H3
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 945 g/kg
Known relevant impurities EU dossier - Toluene <3.0 g/kg
Substance origin Synthetic
Mode of action Systemic, absorbed by roots and young shoots. Inhibition of VLCFA (inhibition of cell division).
CAS RN 106700-29-2
EC number -
CIPAC number 665
US EPA chemical code -
PubChem CID 6450826
Molecular mass (g mol-1) 295.81
PIN (Preferred Identification Name) 2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-1-phenylprop-1-en-1-yl)acetamide
IUPAC name 2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-1-phenylprop-1-enyl)acetamide
CAS name 2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)acetamide
Other status information -
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 Off-white crystalline solid
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 -
Example products using this active
  • Successor
UK LERAP status Yes - see label
Formulation and application details Usually formulated as an emulsifiable concentrate for use as a foliar spray.


ENVIRONMENTAL FATE

for pethoxamid

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) 400 A5 Moderate
Solubility - In organic solvents at 20oC (mg l-1) 117000 A5 - n-Heptane -
250000 A5 - n-Hexane -
250000 A5 - Methanol -
250000 A5 - Ethyl acetate -
Melting point (oC) 37.5 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 200 A5 -
Flashpoint (oC) 299 A5 - Auto-flammability -
Octanol-water partition coefficient at pH 7, 20oC P 9.12 X 1002 Calculated -
Log P 2.96 A5 - @ pH 5 Moderate
Bulk density (g ml-1)/Specific gravity 1.19 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 2.8 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.18 X 10-03 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.34 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 6.69 X 10-03 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 Acidic: 242nm=12100, Neutral: 243nm=12200, Basic: 243nm=12200 A5 -
Surface tension (mN m-1) 53.0 A5 -

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 Not readily biodegradeable
Soil degradation (days) (aerobic) DT50 (typical) 6.3 A5 Non-persistent
DT50 (lab at 20oC) 6.3 A5 Non-persistent
DT50 (field) 14.8 A5 Non-persistent
DT90 (lab at 20oC) 20.9 A5 -
DT90 (field) 84.9 A5 -
DT50 modelling endpoint - - -
Note EU 2016 RAR dossier lab studies DT50 range 5.5-8.1 days, DT90 range 18.2-27.0 days, Soils=4; Field studies range 7.3-22.2 days, DT90 range 73.7-96.0 days, Soils=2
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 14 A5 Slow
Note DT50 49 days, natural sunlight, 40 deg N, 12 hrs daylight.
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 4 to pH 9
Water-sediment DT50 (days) 9.5 A5 Fast
Water phase only DT50 (days) 8.0 A5 Moderately fast

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 - A5 Worse case field value -
Koc -
Notes and range 22.2
Freundlich Kf 4.4 A5 Moderately mobile
Kfoc 211
1/n 0.89
Notes and range EU 2016 RAR dossier Kf range 1.12-9.15 mL/g, Kfoc range 187-241 mL/g, No 1/n range 0.87-0.91, Soils=4
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)-2-sulfoacetamide This metabolite may cause environmental pollution, click here for further information Soil   0.112   Major fraction, Relevant
N-(2-ethoxyethyl)-N-((1Z)-3-hydroxy-2-methyl-1-phenylprop-1-en-1-yl)-2-sulfanylacetamide Soil   0.009   Minor fraction, relevant
2-(N-(2-Methyl-1-phenylprop-1-en-1-yl)-2-sulfoacetamido)acetic acid Soil   0.009   Minor fraction, relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
3-[N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)-carbamoylmethylthio]-D,L-lactic acid pethoxamid metabolite MET-41; TKC-94-S-lactic acid Plant - -
3-[N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)-carbamoylmethylsulfinyl]-D,L lactic acid pethoxamid metabolite MET-50; TKC-94-SO-lactic acid Plant - -
3-N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)-carbamoyl-methylthio]-2-(1-alpha-D-glucopyranosyloxy)propionic acid pethoxamid metabolite MET-58; TKC-94-S-lactic glucoside Plant - -
S-[N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)-carbamoyl-methyl]-D,L-cystein pethoxamid metabolite MET-30; TKC-94 cystein Plant - -
N-(2-amino-4-carboxybutanoic-4-yl)-S-[N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)-carbamoyl-methyl]-D,L-cystein TKC-94-g-glutamyl cystein Plant - -
N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)-2-(2-aminopropion-3-yl)sulfinylacetamide pethoxamid metabolite MET-49; TKC-94-SO-cystein Plant - -
N-(2-carboxyacetyl)-S-[N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)carbamoyl-methyl]-D,L-cystein pethoxamid metabolite MET-47; TKC-94-N-malonyl cystein Plant - -
N-(2-ethoxyethyl)-2-sulfinyl-N-(2-methyl-1-phenyl-1-propenyl)-acetamide TKC-94-thiol Plant - -
N-(2-ethoxyethyl)-2-mercapto-N-(2-methyl-1-phenyl-1-propenyl)-acetamide pethoxamid metabolite MET-43; TKC-94-thiol Plant - -


ECOTOXICOLOGY

for pethoxamid

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) 983 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) 1 A5 Rat, 2 year High
(ppm diet) 25 -
Birds - Acute LD50 (mg kg-1) 1578 A5 Colinus virginianus Moderate
Birds - Short term dietary (LC50/LD50) 1200 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 2.2 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 1.1 A5 Oncorhynchus mykiss, 28 day Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 23 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 2.8 A5 Daphnia magna 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) 0.0247 A5 Lemna gibba Moderate
Non-target plants 0.425 A5 Lolium perenne
Vegetative vigour, ER50
As g product/ha
-
0.592 A5 Lolium perenne
Seedling emergence, ER50
As g product/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) > 149 A5 Pseudokirchneriella subcapitata Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 200 A5 Apis mellifera Low
Oral acute 48 hour LD50 (μg bee-1) > 200 A5 Apis mellifera Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 316 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 8.0 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 100 Mortality
Dose: 1.2 kg/ka
A5 Aphidius rhopalosiphi, imagine
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 100 Mortality
Dose: 1.2 kg ha-1
A5 Typhlodromus pyri, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 12 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for pethoxamid

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) 983 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 4.16 A5 Rat, 4 hr (whole body) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.01 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.08 A5 Rat, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) 0.08 A5 Rat, SF=100 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.02 A5 Dog, 1 year, SF=100 -
Dermal penetration studies (%) 2-8 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded
Occupational Risk of operator exposure where protective equipment is not used - PPE/PPC advised
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 Possible liver & thyroid toxicant

: 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 Not explosive or oxidising
Auto-flammability @ 299 DegC
CLP classification 2013 Health: H302, H317
Environment: H400, H410
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 S2, S24, S37, S46, S60, S61
WHO Classification NL - Not listed
US EPA Classification (formulation) No consensus acorss products or no products available - -
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for pethoxamid

Language Name
English pethoxamid
French -
German Pethoxamid
Danish pethoxamid
Italian -
Spanish -
Greek -
Slovenian petoksamid
Polish petoksamid
Swedish -
Hungarian -
Dutch -

Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk
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