| acrinathrin (Ref: RU38702) |
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Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
SUMMARY
Acrinathrin is a synthetic pyrethroid that has a high insecticidal activity against a range of insects including mites and which is approved for use in the EU. It has a low aqueous solubility, is semi-volatile and, based on its chemical properties, should not leach. Laboratory studies suggest it is moderately persistent in soils but will rapid degrade in aqueous systems. It has a low toxicity to humans but there is some concern that it may bio-accumulate. Acrinathrin is highly toxic to bees and most aquatic species, moderately toxic to birds and earthworms. GENERAL INFORMATION 
for acrinathrin
Description: A pyrethroid ester insecticide and acaricide effective against a range of phytophagous mites and other insects
Example pests controlled: Psyllid; Two-spotted spider mites; Thrips; Leafminers; Aphids
Example applications: Potatoes; Tomatoes; French and runner beans
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1990, France
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | France |
| Date inclusion expires | 31/12/2021 |
| EU Candidate for substitution (CfS) | No |
| Listed in EU database | Yes |
Approved for use (
) or known to be used (
) in the following European countries: 
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 | Acrinathrin contains three chiral centres and one double bond, giving a total of 15 potential isomers other than acrinathrin (8 enantiomeric pairs where acrinathrin is one isomer of an enantiomeric pair). |
| Chemical formula | C26H21F6NO5 |
| Canonical SMILES | CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=CC(=O)OC(C(F)(F)F)C(F)(F)F)C |
| Isomeric SMILES | CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C\C(=O)OC(C(F)(F)F)C(F)(F)F)C |
| International Chemical Identifier key (InChIKey) | YLFSVIMMRPNPFK-WEQBUNFVSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C26H21F6NO5/c1-24(2)18(11-12-20(34)38-23(25(27,28)29)26(30,31)32)21(24)22(35)37-19(14-33)15-7-6-10-17(13-15)36-16-8-4-3-5-9-16/h3-13,18-19,21,23H,1-2H3/t18-,19+,21-/m0/s1 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide, Acaricide | |||
| Substance group | Pyrethroid | |||
| Minimum active substance purity | 970 g/kg | |||
| Known relevant impurities | EU dossier - 1,3-dicyclohexylurea <2mg/kg | |||
| Substance origin | Synthetic | |||
| Mode of action | Contact and stomach action. Neurotoxin. | |||
| CAS RN | 101007-06-1 | |||
| EC number | - | |||
| CIPAC number | 678 | |||
| US EPA chemical code | - | |||
| PubChem CID | 6436606 | |||
| Molecular mass (g mol-1) | 541.44 | |||
| PIN (Preferred Identification Name) | (S)-cyano(3-phenoxyphenyl)methyl (1R,3S)-3-{(1Z)-3-[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]-3-oxoprop-1-en-1-yl}-2,2-dimethylcyclopropane-1-carboxylate | |||
| IUPAC name | (S)-α-cyano-3-phenoxybenzyl (Z)-(1R)-cis-2,2-dimethyl-3-[2-(2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl)vinyl]cyclopropanecarboxylate | |||
| CAS name | (S)-cyano(3-phenoxyphenyl)methyl (1R,3S)-2,2-dimethyl-3-[(1Z)-3-oxo-3-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]-1-propenyl]cyclopropanecarboxylate | |||
| Other status information | - | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | 3 | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | Frankliniella occidentalis Tetranychus urticae |
|||
| Physical state | White to beige coloured powder | |||
| 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 | An oil-water emulsion concentrate usually diluted with water and applied as a foliar spray. | |||
ENVIRONMENTAL FATE
for acrinathrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.0022 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 400000 | A5 - Xylene | - | |
| 17500 | A5 - n-Hexane | - | ||
| 61400 | A4 - Ethanol | - | ||
| 700000 | A5 - Acetone | - | ||
| Melting point (oC) | 81 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 230 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.00 X 1006 | Calculated | - |
| Log P | 6.3 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | - | - | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 4.40 X 10-05 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.80 X 10-02 | A5 | Non-volatile | |
GUS leaching potential index  |
-1.10 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 5.35 X 10-03 | Calculated | - |
| Note | Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral solution 291nm = 466; [Acidic solution 291nm = 642; [Basic solution 308nm = 1760 | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 39.2 | A4 | Moderately persistent |
| DT50 (lab at 20oC) | 40.6 | A5 | Moderately persistent | |
| DT50 (field) | 22 | R3 | Non-persistent | |
| DT90 (lab at 20oC) | 208.5 | A5 | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range: 8.5-111.4 days, DT90 range 28.2-887.1 days; General literature gives DT50 range 9-37 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 2.6 | R4 | - |
| Note | Published literature RL50 range 1.2-6.9 days, 3 undercover crops, various matrices, n=4 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 2.3 | A5 | Moderately fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | W4 | - |
| Note | Stable in acid media. Hydrolysis becomes more important as pH and temp increases: DT50 30 days at pH 7, 30 degC, 15 days at pH 9, 20 degC, <2 days pH9, 37 degC | |||
| Water-sediment DT50 (days) | 18.6 | A5 | Fast | |
| Water phase only DT50 (days) | 6.5 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 744 | A5 | Non-mobile |
| Koc | 48231 | |||
| Notes and range | EU dossier Kd range 302-1350 mL/g, Koc range 24108-90061 mL/g, Soils=5 | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| cis-des-hexafluoroisopropyl acrinathrin (Ref: DP-A) | Soil | 0.097 | Major fraction, Relevant | |
| (2Z)-3-(3-((2-amino-2-oxo-1-(3-phenoxyphenyl)ethoxy)carbonyl)-2,2-dimethylcyclopropyl)prop-2-enoic acid |
Soil | 0.105 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| unknown Note: Minor metabolite |
3-PBAc | Soil; Surface water | Soil: 0.076 | - |
| A-A Note: DT50 7.4 days; Koc 88880 |
- | Soil | 0.057 | - |
| alphaR A-A | - | Soil | 0.029 | - |
| 3-PBAld | - | Groundwater | - | - |
| 1,3-dicyclohexylurea (Ref: AEB007816) |
- | Impurity | - | - |
| cyclopropyl-di-acid (Ref: RU 50158) Note: Minor metabolite |
DP-DPB-A | Animal (Urinary); Plant | Soil: 0.076 | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 538 | A5 | Threshold for concern |
| CT50 (days) | 3 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A4 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 2.4 | L3 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Anas platyrhynchos | Low | |
| Birds - Short term dietary (LC50/LD50) | 1000 mg kg feed-1 | A5 Anas platyrhynchos | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.0061 | A5 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.00083 | A5 Oncorhynchus mykiss, 28 day | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.000022 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.0000032 | A5 Daphnia magna | High | |
| 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) | 0.000031 | A5 Chironomus riparius, whole system | High | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | 888 | A5 Mungbean Vegetative vigour, ER50 as g/ha |
- | |
| > 1000 | A5 Mungbean Seedling emergence, ER50 as g/ha |
- | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.0035 | A5 Selenastrum capricornutum | High | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 0.084 | A5 | High |
| Oral acute 48 hour LD50 (μg bee-1) | 0.077 | A5 | High | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 100 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 1.6 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | 1.0 | A5 Folsomia candida, NOEC | - |
| Other arthropod (1) | LR50 g ha-1 | 0.046 | Mortality A5 Alphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 0.006 | Mortality A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1 mg kg-1 soil, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 0.000026 | A5 Micro-invertebrates NOEC | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for acrinathrin
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) | > 5000 | A4 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 1.21 | A5 Rat, 4 hr (whole body) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.01 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.01 | A5 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) | 0.007 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 2.0-8.3 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | No unacceptable risks to bystanders identified as long as access to spray area prohibited during spraying | ||
| Occupational | Risks identified - protective clothing and equipment advised | |||
| 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 | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | May cause diarrhoea and vomiting if ingested Possible kidney and blood toxicant |
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: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | None allocated at this time | |||
| EC Risk Classification |
Carcinogen category 3: R40 Xn - Harmful: R21, R20 N - Dangerous for the environment: R50/53 |
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| EC Safety Classification |
S1/2, S24, S36/37, S45, S46, S60, S61 | |||
| WHO Classification | U | - | Unlikely to present an acute hazard | |
| US EPA Classification (formulation) | IV | - | Caution - Not acutely toxic | |
| UN Number | Usually 3077 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | acrinathrin |
| French | acrinathrine |
| German | Acrinathrin |
| Danish | acrinathrin |
| Italian | acrinatrina |
| Spanish | acrinatrina |
| Greek | - |
| Slovenian | akrinatrin |
| Polish | akrynatryna |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk