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acrinathrin (Ref: RU38702)
** acrinathrine ** AE F076003 ** HOE 76003 ** NU 702 ** Translations

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 Click here for an explantaion of the general chemical status 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: 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

Chemical structure: Click here for further information on the general chemical status information used on this site
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
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
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 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
  • Cheminova
Example products using this active
  • Rufast
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 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) 0.0022 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 Click here for a note on the limitations of the GUS 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 Click here for a note on the limitations of the SCI-GROW index 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 Click here for a note on the limitations of the 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 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) 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 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 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 Click here for further information on 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 This metabolite may cause environmental pollution, click here for further information 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 -


ECOTOXICOLOGY

for acrinathrin

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) 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 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 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

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues May cause diarrhoea and vomiting if ingested
Possible kidney and blood toxicant

: 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 Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 None allocated at this time
EC Risk Classification Click here to view information omn the EU risk phrases Carcinogen category 3: R40
Xn - Harmful: R21, R20
N - Dangerous for the environment: R50/53
EC Safety Classification Click here to view information omn the EU safety phrases 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 Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for acrinathrin

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