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Oxolinic acid
Last updated: 24/02/2021
(Also known as: dioxacin; crop antibiotic)

SUMMARY
Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate Ecotoxicity Human health
Environmental fate
High alert:
Potential for particle bound transport: High
Warning:
Significant data are missing
Ecotoxicity
Moderate alert:
Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate
Human health
High alert:
Neurotoxicant
Warning:
Significant data are missing
GENERAL INFORMATION
Description
An antibacterial drug used to treat urinary tract and other infections. Also shows activity against plant-pathogenic bacteria and so used as a crop antibiotic in a few countries.
Example pests controlled
Seed-borne pathogenic 'Burkholderia glumae' that causes grain rot, seedling rot, fire blight and bacterial panicle blight.
Example applications
Apples and pears; Rice
Efficacy & activity
-
Availability status
-
Introduction & key dates
1989, first introduced Japan
UK regulatory status
UK COPR regulatory status
Not applicable
Date COPR inclusion expires
Not applicable
UK LERAP status
Not applicable
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not applicable
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
Approved for use (✓) under EC 1107/2009 in the following EU Member States
ATAustria
BEBelgium
BGBulgaria
CYCyprus
CZCzech Republic
DEGermany
DKDenmark
EEEstonia
ELGreece
                 
ESSpain
FIFinland
FRFrance
HRCroatia
HUHungary
IEIreland
ITItaly
LTLithuania
LULuxembourg
                 
LVLatvia
MTMalta
NLNetherlands
PLPoland
PTPortugal
RORomania
SESweden
SISlovenia
SKSlovakia
                 
Additional information
Also used in
Israel
Chemical structure
Isomerism
-
Chemical formula
C₁₃H₁₁NO₅
Canonical SMILES
CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
KYGZCKSPAKDVKC-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
oxolinic acid -
General status
Pesticide type
Veterinary substance, Crop antibiotic
Substance group
Quinolone
Minimum active substance purity
>98%
Known relevant impurities
8-hydroxy-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid, ethyl 5-ethyl-8-oxo-5,8-dihydro-1,3-ioxolo(4,5-gquinoline-7-carboxylate, 5-methyl-8-oxo-5,8-dihydro-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid
Substance origin
Synthetic
Mode of action
Works via two routes, by inhibiting the enzyme DNA gyrase and also acts as a dopamine reuptake inhibitor.
CAS RN
14698-29-4
EC number
238-750-8
CIPAC number
-
US EPA chemical code
-
PubChem CID
-
Molecular mass
261.23
PIN (Preferred Identification Name)
-
IUPAC name
5-ethyl- 8-oxo- 5,8-dihydro [1,3] dioxolo [4,5-g] quinoline- 7-carboxylic acid
CAS name
5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid
Other status information
Annex 1 EC Reg. 2377/90
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
31
Examples of recorded resistance
B. glumae
Physical state
White to pale yellow crystalline solid
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Sumitomo Chemical Company
Example products using this active
  • Starner 20% WP
Formulation and application details
Usually administered orally in feed, drinking water or as a bolus for animal health applications or as a spray or seed treatment for plant pathogenic uses.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
3.2
P3 P = Other governments and regulators
3 = Unverified data of known source
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
10000
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Hexane
-
10000
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Xylene
-
10000
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Methanol
-
Melting point (°C)
315
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
Not expected to self ignite; Not highly flammable
P4 P = Other governments and regulators
4 = Verified data
-
Octanol-water partition coefficient at pH 7, 20 °C
P
4.68 X 1001 Calculated -
Log P
1.67
R4 R = Peer reviewed scientific publications
4 = Verified data
Low
Bulk density (g ml⁻¹)
1.55
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
6.3
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
-
-
Vapour pressure at 20 °C (mPa)
0.147
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
550
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Very persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Data for superficial sediments DT₅₀ 150-1000 days, various sediment depths
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
- - -
Note
88% degraded after 9 days
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
-
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
P4 P = Other governments and regulators
4 = Verified data
Slightly mobile
Koc
2260
Notes and range
Literature range for Koc is 14 to 4510
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
1.77 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
6.11 X 10-02 Calculated -
Note
-
Potential for particle bound transport index
High Calculated -
Potential for loss via drain flow
Slightly mobile Calculated -
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
1-ethyl-1,4-dihydro-7-hydroxy-6-methoxy-6-oxoquinoline-3-carboxylic acid - Rat, Rabbit, Dog - -
Oxolinoyl-beta-D-glucuronic acid
Note: Active metabolite
- Rat (Uriinary), Rabbit (Urinary), Dog (Urinary) - -
- - - - -
5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo-[4,5,g]quinoline-7-carboxylic acid - Human - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 525
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Rat
Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 2000
P4 P = Other governments and regulators
4 = Verified data
Colinus virginianus
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 10
P3 P = Other governments and regulators
3 = Unverified data of known source
Cyprinus carpio
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
35.0
P3 P = Other governments and regulators
3 = Unverified data of known source
Oncorhynchus mykiss 29 day
Low
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
4.6
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.38
R4 R = Peer reviewed scientific publications
4 = Verified data
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)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
16
R4 R = Peer reviewed scientific publications
4 = Verified data
Selenastrum capricornutum
Low
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)
> 20
P4 P = Other governments and regulators
4 = Verified data
Moderate
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
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)
- - -
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
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)
> 1000
P4 P = Other governments and regulators
4 = Verified data
Eisenia foetida
Low
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 525
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Rat
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
P4 P = Other governments and regulators
4 = Verified data
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
1.7
P4 P = Other governments and regulators
4 = Verified data
Rat
-
Other Mammal toxicity endpoints
Intravenous LD₅₀ = 177 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Mouse
-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
MRLs
European
EU MRL pesticide database 
Great Britain
GB MRL Register 
Notes
-
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found No data found
Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
Yes, known to cause a problem
No data found
Eye irritant Phototoxicant  
Yes, known to cause a problem
Yes, known to cause a problem
 
General human health issues
Harmfull if swallowed
May cause visual disturbances, fever, anorexia, urticaria, and photosensitivity reactions
May cause gastrointestinal tract problems
Handling issues
Property
Value and interpretation
General
Corrosive
Not explosive
CLP classification 2013
-
EC Risk Classification
Xn - Harmful: R22, R34
Xi - Irritant: R36, R37, R38
EC Safety Classification
-
WHO Classification
None - not a ppp
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
oxolinic acid
French
acide oxolinique
German
-
Danish
-
Italian
-
Spanish
acido oxolinico
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 24/02/2021
Contact: aeru@herts.ac.uk
Please cite as: Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242