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GET ADDITIONAL DATA HERE!
oxolinic acid
** dioxacin ** crop antibiotic ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
Further data may be found in the VSDB

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

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

EC Regulation 1107/2009 (repealing 91/414):
Status Not applicable
Dossier rapporteur/co-rapporteur Not applicable
Date inclusion expires Not applicable
EU Candidate for substitution (CfS) Not applicable
Listed in EU database No

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: Israel

Chemical structure: Click here for further information on the general chemical status information used on this site
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

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Oxolinic acid - 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 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-g
quinoline-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 (g mol-1) 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 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
  • Sumitomo Chemical Company
Example products using this active
  • Starner 20% WP
UK LERAP status Not applicable
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

for oxolinic acid

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) 3.2 P3 Low
Solubility - In organic solvents at 20oC (mg l-1) 10000 Q3 - Hexane -
10000 Q3 - Xylene -
10000 Q3 - Methanol -
Melting point (oC) 315 Q3 -
Boiling point (oC) - - -
Degradation point (oC) - - -
Flashpoint (oC) Not expected to self ignite; Not highly flammable P4 -
Octanol-water partition coefficient at pH 7, 20oC P 4.68 X 1001 Calculated -
Log P 1.67 R4 Low
Bulk density (g ml-1)/Specific gravity 1.55 Q3 -
Dissociation constant (pKa) at 25oC 6.3 R3 -
Note:
Vapour pressure at 20oC (mPa) 0.147 Q3 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) - - -
GUS leaching potential index Click here for a note on the limitations of the GUS 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 Click here for a note on the limitations of the SCI-GROW index Value 6.11 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 High
Maximum UV-vis absorption L mol-1 cm-1 - - -
Surface tension (mN m-1) - - -

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) 550 R3 Very persistent
DT50 (lab at 20oC) - - -
DT50 (field) - - -
DT90 (lab at 20oC) - - -
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 20oC and pH 7 Value - R4 -
Note -
Water-sediment DT50 (days) - - -
Water phase only DT50 (days) - - -

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 - P4 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 -

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

for oxolinic acid

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) - - -
CT50 (days) - -
Mammals - Acute oral LD50 (mg kg-1) > 525 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 P4 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) > 10 P3 Cyprinus carpio Moderate
Fish - Chronic 21 day NOEC (mg l-1) 35.0 P3 Oncorhynchus mykiss, 29 day Low
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 4.6 R4 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.38 R4 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 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 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 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

for oxolinic acid

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) > 525 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 P4 Rat -
Mammals - Inhalation LC50 (mg l-1) 1.7 P4 Rat -
Other Mammal toxicity endpoints Intravenous LD50 = 177 mg kg-1 V3 Mouse -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) - - -
ARfD - Acute Reference Dose (mg kg-1bw day-1) - - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) - - -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public -
Occupational -
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; E0

-

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

General human health issues Harmfull if swallowed
May cause visual disturbances, fever, anorexia, urticaria, and photosensitivity reactions
May cause gastrointestinal tract problems
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 Corrosive
Not explosive
CLP classification 2013 -
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22, R34
Xi - Irritant: R36, R37, R38
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification None - not a ppp - -
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for oxolinic acid

Language Name
English oxolinic acid
French acide oxolinique
German -
Danish -
Italian -
Spanish acido oxolinico
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -

Record last updated: Thursday 05 March 2020
Contact: aeru@herts.ac.uk