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flumioxazin (Ref: S 53482)
** flumioxazine ** Translations

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

SUMMARY

A herbicide that currently has approval for use in the EU. It has a low aqueous solubility, relatively volatile and, based on its chemical properties, the risk of leaching to groundwater is low. It is not usually persistent it either water or soil systems. It has a low mammalian toxicity but a high risk of bioconcentration. There are also risks associated with reproduction/development and flumioxazin is a skin and eye irritant. It is highly toxic to algae and aquatic plants, moderately toxic to earthworms, honeybees, fish and aquatic invertebrates. However flumioxazin presents less risk to birds.

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

Description: A herbicide for pre-emergence broad-spectrum control of weeds particularly in or close to water

Example pests controlled: Eurasian watermilfoil, Curlyleaf pondweed, some species of filamentous algae

Example applications: Soybeans; Peanuts; Vegetables; Fruit; Ornamentals; Forestry; Aquatic areas

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1994, Argentina

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Czech Republic/France
Date inclusion expires 30/06/2019
EU Candidate for substitution (CfS) Yes - toxic for reproduction
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 -
Chemical formula C19H15FN2O4
Canonical SMILES C#CCN1C(=O)COC2=CC(=C(C=C21)N3C(=O)C4=C(C3=O)CCCC4)F
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) FOUWCSDKDDHKQP-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C19H15FN2O4/c1-2-7-21-15-9-14(13(20)8-16(15)26-10-17(21)23)22-18(24)11-5-3-4-6-12(11)19(22)25/h1,8-9H,3-7,10H2
2D structure diagram/image available? Yes

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Flumioxazin - Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group N-phenylphtalamides
Minimum active substance purity 960 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Induces accumulation of porphyrins leading to membrane damage. Inhibition of protoporphyrinogen oxidase (PPO).
CAS RN 103361-09-7
EC number -
CIPAC number 578
US EPA chemical code 129034
PubChem CID 92425
CLP index number 613-166-00-X
Molecular mass (g mol-1) 354.33
PIN (Preferred Identification Name) -
IUPAC name N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide
CAS name 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) E
Herbicide Resistance Classification (WSSA) 14
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state White when pure (99.6%), yellow-brown powder (97.65)
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
  • Interfarm
  • Sumitomo
Example products using this active
  • Digital
  • Guillotine
  • Summimax
UK LERAP status Buffer probably required in UK - see product label
Formulation and application details Often supplied as a soluble concentrate which is mixed with water and applied as a spray.


ENVIRONMENTAL FATE

for flumioxazin

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) 0.786 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 17000 A5 - Acetone -
17800 A5 - Ethyl acetate -
25 A5 - Hexane -
1600 A5 - Methanol -
Melting point (oC) 203.5 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 273.3 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 3.55 X 1002 Calculated -
Log P 2.55 A5 Low
Bulk density (g ml-1)/Specific gravity 1.5 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.32 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 0.145 A5 Moderately volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.41 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 3.13 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 Neutral solution: 215nm = 58211, 289nm = 6748; [Acidic solution: 215nm 57861, 289nm = 6736
Basic solution: 220nm = 27512, 299nm = 9781
A5 -
Surface tension (mN m-1) 70.9 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 -
Soil degradation (days) (aerobic) DT50 (typical) 21.9 A5 Non-persistent
DT50 (lab at 20oC) 21.9 A5 Non-persistent
DT50 (field) 17.6 A5 Non-persistent
DT90 (lab at 20oC) 71 A5 -
DT90 (field) 58.3 A5 -
DT50 modelling endpoint - - -
Note EU dossier Lab studies DT50 range 11.8-34.7 days, DT90 range 47.7-297 days; Field studies DT50 range 15.6-19.5 days, DT90 range 51.8-64.8 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 1 A5 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 1 A5 Non-persistent
Note pH sensitive: DT50 at pH 3-5 days; at pH 9 14-23 minutes - all at 25 degC
Water-sediment DT50 (days) 0.4 A5 Fast
Water phase only DT50 (days) 2 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 Slightly mobile
Koc 889
Notes and range Other sources: 2240 mL/g (DW3)
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
cyclohex-1-ene-1,2-dicarboxylic acid Soil   0.066   Minor fraction, Relevant
4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Soil   0.051   Minor fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
6-amino-7-fluoro-4-(2-propynyl)-1,4-benzoxazin-3(2H)-one APF Water (Hydrolysis); Soil 0.868 -
7-fluoro-5[(2-carboxy-cyclohexenoyl)amino]-4-(2-propynyl)-1,4-benzoxazin-2(2H)-one 482-HA Surface water (Hydrolysis) - -
3,4,5,6-tetrahydrophthalic acid anhydride 1-TPA Water (Hydrolysis) - -
N-(2-propynyl)-4-[4-carboxy-3-fluoro-2-(3,4,5,6-tetrahydrophthalimido)-2-butenylidene]azetidine-2-one 482-PHO Water (Photolysis) - -
disodium cyclohex-1-ene-1,2-dicarboxylate THPA-2Na - - -
N-(2-propynyl)-4-[4-carboxy-3-fluoro-2-(2-carboxy-1-cyclohexencarbonylamino)-2-butenylidene]azetidine-2-one PHO-HA Water - -
(1S,2S)-2-{[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbamoyl}cyclohexanecarboxylic acid SAT-482-HA-2 - - -


ECOTOXICOLOGY

for flumioxazin

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) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - A5 Rat -
(ppm diet) 300 -
Birds - Acute LD50 (mg kg-1) > 2250 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 500 ppm A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 2.3 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.37 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 5.9 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.057 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) 0.73 A5 Chironomus riparius Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.00035 A5 Lemna gibba High
Non-target plants 4.96 A5 Sugar beet
Vegetative vigour, ER50
as g/ha
-
14.81 A4 Sugar beet
Seedling emergence, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 0.000852 A4 Raphidocelis subcapitata, 72 hour High
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 200 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 229.1 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 491 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-1 600 >
A5 Aphidius rhopalosiphi
-
% Effect 75 Mortality
Parasitism
Dose: 0.6 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 600 >
A5 Typhlodromus pyri
-
% Effect 2 Mortality and Fertility
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: 1.2 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for flumioxazin

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) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 3.93 A5 Rat, 4 hr (whole body) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.009 A5 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.05 A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.018 A5 -
Dermal penetration studies (%) 2.8-18.5% A5 concentration dependent -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public Estimated low risk to bystanders and the public
Occupational Occupational exposure may occur through dermal and inhalation routes
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 Some evidence chronic exposure can cause anaemia

: 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 dust
Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H360D
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Reproduction risk category 2: R61
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S45, S53, S60, S61
WHO Classification NL - Not listed
US EPA Classification (formulation) No consensus across products or no products available - -
UN Number Usually 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for flumioxazin

Language Name
English flumioxazin
French flumioxazine
German Flumioxazin
Danish flumioxazin
Italian flumioxazine
Spanish flumioxazina
Greek flumioxazin
Slovenian flumioksazin
Polish flumioksazyna
Swedish -
Hungarian flumioxazin
Dutch flumioxazin

Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk