| azinphos-ethyl (Ref: BAY 16259) |
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SUMMARY
Azinphos-ethyl is an organophosphate insecticide that is not approved for use in the EU. It has a low aqueous solubility, relatively volatile and is not expected to leach to groundwater. It may be moderately persistent in some soil systems but is not expected to be persistent in water. It is toxic to mammals and there is also concern regarding its potential to bioaccumulate. It is a neurotoxicant and an acetyl cholinesterase inhibitor. Azinphos-ethyl is highly toxic to birds, fish and aquatic invertebrates. It is moderately toxic to honeybees. GENERAL INFORMATION 
for azinphos-ethyl
Description: A benzotriazine organothiophosphate insecticide and organothiophosphate acaricide for the control of sucking and chewing pests
Example pests controlled: Spider mites; Aphids; Caterpillers; Potato bugs including Colorado beetles; Oat mites; Tocks
Example applications: Cotton; Rice; Tobacco; Melons; Tomatoes; Potatoes; Hops; Beet crops; Citrus; Soybeans; Apples
Efficacy & activity: -
Availability status: Unknown
Introduction & key dates: 1955
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Germany |
| Date inclusion expires | Expired |
| EU Candidate for substitution (CfS) | - |
| Listed in EU database | Yes |
Approved for use (
) or known to be used (
) in the following European countries: 
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 |
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Chemical structure:
| Isomerism | - |
| Chemical formula | C12H16N3O3PS2 |
| Canonical SMILES | CCOP(=S)(OCC)SCN1C(=O)C2=CC=CC=C2N=N1 |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | RQVGAIADHNPSME-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C12H16N3O3PS2/c1-3-17-19(20,18-4-2)21-9-15-12(16)10-7-5-6-8-11(10)13-14-15/h5-8H,3-4,9H2,1-2H3 |
| 2D structure diagram/image available? | Yes |
Cambridge Crystallographic Data Centre diagrams:
| Common Name | Relationship | Link |
| Azinphos-ethyl | - |  |
General status:
| Pesticide type | Insecticide, Acaricide | |||
| Substance group | Organophosphate | |||
| Minimum active substance purity | - | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Non-systemic, contact and stomach action. Cholinesterase inhibitor. Ovicidal. | |||
| CAS RN | 2642-71-9 | |||
| EC number | 220-147-6 | |||
| CIPAC number | 485 | |||
| US EPA chemical code | 058002 | |||
| PubChem CID | 17531 | |||
| Molecular mass (g mol-1) | 345.38 | |||
| PIN (Preferred Identification Name) | O,O-diethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] phosphorodithioate | |||
| IUPAC name | S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-diethyl phosphorodithioate | |||
| CAS name | O,O-diethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) phosphorodithioate | |||
| Other status information | Severe Marine Pollutant; Chemical subject to PIC regulations | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | 1B | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | Culex pipiens pipiens Myzus persicae Phorodon humuli |
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| Physical state | Colourless needle-like crystals | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Available in a variety of formulations including dusts, emulsifiable concentrates, ULVs and wettable powders. | |||
ENVIRONMENTAL FATE
for azinphos-ethyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 4.5 | L3 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 3500 | L2 - n-Hexane | - | |
| 35000 | L2 - Isopropanol | - | ||
| 1000000 | L3 - Dichloromethane | - | ||
| 1000000 | L3 - Toluene | - | ||
| Melting point (oC) | 50 | L3 | - | |
| Boiling point (oC) | 111 | V3 | - | |
| Degradation point (oC) | - | - | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | V3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.51 X 1003 | Calculated | - |
| Log P | 3.18 | L3 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.28 | L3 | - | |
| Dissociation constant (pKa) at 25oC | - | - | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 0.32 | L3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 3.05 X 10-06 | L3 | Non-volatile | |
GUS leaching potential index  |
1.40 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 3.46 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 50 | L2 | Moderately persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Best available data | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 10 | R4 | - |
| Note | Apple fruit, n=1; Apples in store RL50 range 83-91 days, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 0.4 | K4 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 13 | K4 | Non-persistent |
| Note | - | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | P2 | Slightly mobile |
| Koc | 1500 | |||
| Notes and range | Other source Koc 1700 mL/g estimate (CA2) | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| desethyl azinphos-ethyl | Soil | - | - | |
| sulfonmethylbenzamid | Soil | - | - | |
ECOTOXICOLOGY
for azinphos-ethyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 101 | Q2 Estimated | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 12 | F4 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L2 Rat, 2 year | - |
| (ppm diet) | 2 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 12.5 | L3 Coturnix japonica | High | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.08 | L3 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.0002 | L3 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| 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) | - | - | - | |
| 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) | > 1.39 | R4 | 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) | - | - | - | |
| 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 azinphos-ethyl
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | 12 | F4 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | 500 | L2 Rat, 24hr | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.15 | L3 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.03 | Q3, as ug/day, India | - | |
| 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 | List I; List II | - | - | |
| Exposure Routes | Public | Consumer exposure should be low or non-existent since azinphos ethyl is no longer produced or used in most of the developed world | ||
| Occupational | Occupational exposure should be low or non-existent since azinphos ethyl is no longer produced or used in most of the developed world | |||
| 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 | |||
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A3; B0; C0; D0; E0 | - |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | No further information available | |||||||
| 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 |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
IMDG Transport Code is 6.1 | |||
| CLP classification 2013 | Health: H300, H311 Environment: H400, H410 |
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| EC Risk Classification |
T+ - Very toxic: R28 T - Toxic: R24 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S1/2, S28, S45, S61, S36/37, S60 | |||
| WHO Classification | Ib | - | Highly hazardous | |
| UN Number | Active 2783, liquid products usually 3018 | |||
| Waste disposal & packaging |
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TRANSLATIONS
for azinphos-ethyl
| Language | Name |
| English | azinphos-ethyl |
| French | azinphos-ethyl |
| German | Azinphos-ethyl |
| Danish | azinphos-ethyl |
| Italian | azinfos-etile |
| Spanish | azinfos-etil |
| Greek | azinphos-ethyl |
| Slovenian | azinfosetil |
| Polish | azinofos etylowy |
| Swedish | - |
| Hungarian | azinphos-ethyl |
| Dutch | azinfos-ethyl |
Record last updated: Tuesday 30 October 2018
Contact: aeru@herts.ac.uk