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cycloxydim (Ref: BAS 517H)
** cycloxydime ** LAB 172 999 ** Translations

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

SUMMARY

Cycloxydim is a systemic herbicide approved for use in the EU. It is moderately soluble in aqueous solution, is unlikely to leach to groudnwater and is relatively volatile. It is not persistent in soils and is unlikely to persist in aquatic systems due to rapid aqueous photolysis. It has a low mammalian toxicity and, whilst the chemical properties suggest it may bioaccumulate, that does not appear to happen in practice. It is a skin and eye irritant. It is moderately toxic to birds, honeybees, earthworms and aquatic invertebrates. However, its is not particularly toxic to fish and other aquatic organisms.

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

Description: A post-emergence foliar applied grass herbicide

Example pests controlled: Black grass; Volunteer cereals; Black bent; Onion couch

Example applications: Sugarbeet; Fodder beet; Mangels; Linseed; Vegetables including brassicas, beans, peas, leeks, carrots, swede; Fruit including strawberries; Potatoes

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1989, France

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Netherlands/Denmark
Date inclusion expires 31/05/2021
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 A chiral molecule existing in both the E- and the Z-forms depending on the polarity and the pH of the respective environment in which the molecule sits. The Z-isomer is predominate in acidic situations.
Chemical formula C17H27NO3S
Canonical SMILES CCCC(=C1C(=O)CC(CC1=O)C2CCCSC2)NOCC
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) GGWHBJGBERXSLL-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C17H27NO3S/c1-3-6-14(18-21-4-2)17-15(19)9-13(10-16(17)20)12-7-5-8-22-11-12/h12-13,19H,3-11H2,1-2H3/b18-14-
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 Cyclohexanedione
Minimum active substance purity 940 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Selective, systemic, absorbed by foliage. Inhibits fatty acid synthesis. An acetyl CoA carboxylase inhibitor (ACCase).
CAS RN 101205-02-1
EC number 405-230-9
CIPAC number 510
US EPA chemical code -
PubChem CID 91765
Molecular mass (g mol-1) 325.46
PIN (Preferred Identification Name) (5E)-2-[(1E)-N-ethoxybutanimidoyl]-3-hydroxy-5-[(3E)-thian-3-yl]cyclohex-2-en-1-one
IUPAC name (5RS)-2-[(EZ)-1-(ethoxyimino)butyl]-3-hydroxy-5-[(3RS)-thian-3-yl]cyclohex-2-en-1-one
CAS name 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) A
Herbicide Resistance Classification (WSSA) 1
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Alopecurus myosuroides
Avena sterilis
Physical state Colourless crystals
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
  • Greencrop
  • Teliton
Example products using this active
  • Focus 10 EC
  • Laser
  • Focus Ultra
  • Stratos Ultra
UK LERAP status None
Formulation and application details Often supplied as an emulsion concentrate which is mixed with water and applied as a spray to dry foliage.


ENVIRONMENTAL FATE

for cycloxydim

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) 53 A5 Moderate
Solubility - In organic solvents at 20oC (mg l-1) 250000 A4 - Acetone -
810000 C4 - Ethanol -
29000 C4 - Hexane -
250000 L3 - Ethyl acetate -
Melting point (oC) 37.1 A5 -
Boiling point (oC) Decomposes before boiling A3 -
Degradation point (oC) 200 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 2.29 X 1001 Calculated -
Log P 1.36 A5 Low
Bulk density (g ml-1)/Specific gravity 1.12 L3 -
Dissociation constant (pKa) at 25oC 4.17 A5 -
Note: Weak acid
Vapour pressure at 20oC (mPa) 0.01 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 6.14 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -0.42 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 4.43 X 10-04 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 Neutral solution: >290nm = 10; [Methanol: 210nm = 7200, 227nm = 4100, 259nm = 1000, 278nm = 9300, 290nm = 7900, 300nm = 4400 A5 -
Surface tension (mN m-1) 58.0 A5 at 20oC, 0.5% 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) 0.65 Click here to see a warning relating to modelling and this active substance A5 Non-persistent
DT50 (lab at 20oC) 0.65 A5 Non-persistent
DT50 (field) 5 Y4 Non-persistent
DT90 (lab at 20oC) 3.47 A5 -
DT90 (field) - - -
DT50 modelling endpoint - - -
Note EU Dossier lab studies DT50 range 0.2-2.6 days, DT90 range 0.5-8.6 days; Other lab studies DT50 1-12 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 0.05 B4 Fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 172 A5 Persistent
Note pH sensitive: DT50 1.7 days at pH 3, 8.3 days at pH 5, 172 days at pH 7, 206 days at pH 9 all at 24 degC
Water-sediment DT50 (days) 20.8 A5 Fast
Water phase only DT50 (days) 4.5 K4 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 0.38 A5 Mobile
Koc 59
Notes and range EU dossier Kd range 0.03-0.73 mL/g, Koc range 5-183 mL/g, Soils=4; Other studies 5-185 mL/g
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity None but little adsorption observed on soils pH >6

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
cycloxydim sulfoxide (Ref: BH 517-TSO) This metabolite may cause environmental pollution, click here for further information Soil   0.904   Major fraction, Relevant
cycloxydim sulfone (Ref: BH 517-TSO2) Soil   0.095   Minor fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
2-[1-(ethoxyimino)butyl]-3,5-dihydroxy-5-(3-thianyl)-2-cyclohexen-1-one
(Ref: BH 517-5-OH TS)
- Plant - -
2-[1-(ethoxyimino)butyl]-3,5-dihydroxy-5-(3-thianyl)-2-cycloexene-1-one S-oxide
(Ref: BH 517-5-OH-TSO)
- Plant - -
2-[1-(ethoxyimino)butyl]-3,5-dihydroxy-5-(3-thianyl)-2-cycloexene-1-one S-dioxide
(Ref: BH 517-5-OH-TSO2)
- Plant - -
(Ref: BH 517-6-OH-T2SO) - Plant - -
3-hydroxy-3-(3-thianyl)glutaric acid S-dioxide
(Ref: BH 517-OH-TGSO2)
- Plant - -
2-butanimidoyl-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)cyclohex-2-en-1-one
(Ref: BH 517-T1S)
Note: Low aquatic toxicity
- Water; Sediment; Animal - -
2-butanimidoyl-3-hydroxy-5-(1-oxidotetrahydro-2H-thiopyran-3-yl)cyclohex-2-en-1-one
(Ref: BH 517-T1SO)
Note: Low aquatic toxicity
- Animal; Water; Sediment - -
2-butanimidoyl-5-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-3-hydroxycyclohex-2-en-1-one
(Ref: BH 517-T1SO2)
- Plant - -
2-propyl-6-(3-thianyl)-4,5,6,7-tetrahydrobenzoxazol-4-one
(Ref: BH 517-T2S)
cycloxydim oxazole metabolite Plant; Water - -
2-propyl-6-(3-thianyl)-4,5,6,7-tetrahydrobenzoxazol-4-one S-dioxide
(Ref: BH 517-T2SO2)
Note: Risk to groundwater
cycloxydim oxazole metabolite Plant; Soil - -
3-(1-oxidotetrahydro-2H-thiopyran-3-yl)pentanedioic acid
(Ref: BH 517-TGSO)
- Plant; Soil - -
3-(3-thianyl)glutaric acid S- dioxide
(Ref: BH 517-TGSO2)
- Plant - -


ECOTOXICOLOGY

for cycloxydim

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) 3940 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) > 10 A5 Dog High
(ppm diet) > 300 -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) 496.8 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) > 220 A5 Oncorhynchus mykiss Low
Fish - Chronic 21 day NOEC (mg l-1) 21.5 A5 Oncorhynchus mykiss Low
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 70.8 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 62.5 A5 Daphnia magna Low
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) > 100 A5 Lemna gibba Low
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 74.9 A5 Anabaena flos-aquae Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) 10 Q2 Unknown species Low
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 101.7 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida, corr 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 0
23.3
Mortality
Reproduction
Dose: 0.6 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 19.6
6.1
Mortality
Reproduction
Dose: 0.6 kg ha-1
A5 Typhlodromus pyri, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 2.5 kg ha-1, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for cycloxydim

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) 3940 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.28 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.07 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 2.0 A4 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 A4 Dog, SF=100 -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Negligible risk to bystanders
Occupational PPE/PPC recommended
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 No further information available

: 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 Flammable
Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H361d
EC Risk Classification Click here to view information omn the EU risk phrases Reproduction risk category 3: R63
H - Handling risks: R11
N - Dangerous for the environment: R53
EC Safety Classification Click here to view information omn the EU safety phrases S1/2, S13, S20/21, S36/37
WHO Classification III - Slightly hazardous
US EPA Classification (formulation) IV - Caution - Not acutely toxic
UN Number Usually 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for cycloxydim

Language Name
English cycloxydim
French cycloxydime
German Cycloxydim
Danish cycloxydim
Italian cicloxidim
Spanish cicloxidim
Greek -
Slovenian cikloksidim
Polish cykloksydym
Swedish cykloxidim
Hungarian cikloxidim
Dutch cycloxydim

Record last updated: Tuesday 22 May 2018
Contact: aeru@herts.ac.uk