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alpha-cypermethrin (Ref: OMS 3004)
** alphacypermethrin ** alphamethrin ** FMC 63318 ** FMC 39391 ** Translations

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

SUMMARY

Alpha-cypermethrin is a widely used pyrethroid insecticide that is approved for use in the EU. It has a low aqueous solubility, in non-volatile and, based on its chemical properties, is not expected to leach to groundwater. However, it is considered to be a serious water pollutant. It is moderately persistent in soil and has been known to persist in water. It is highly toxic to mammals and a recognised irritant. It is relatively non-toxic to birds but is highly toxic to most aquatic organisms and honeybees. It is moderately toxic to earthworms.

GENERAL INFORMATION
for alpha-cypermethrin

Description: An insecticide for control of chewing and sucking insects in a wide range of crops. Also has veterinary treatment applications.

Introduction: 1983, first reported; circa 1985, first introduced

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Belgium
Date inclusion expires 28/02/2015

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia

General status:
Pesticide type Insecticide, Veterinary substance
Substance group Pyrethroid
Substance origin Synthetic
Mode of action Non-systemic with contact and stomach action. Sodium channel modulator.
CAS RN 67375-30-8
EC number 257-842-9
CIPAC number 454
US EPA chemical code -
Chiral molecule Chiral or specific isomer of a chiral molecule
Chemical formula C22H19Cl2NO3
SMILES Cl/C(Cl)=C/C3C(C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C
International Chemical Identifier (InChI) InChI=1/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18?,20-/m0/s1
Structure diagram/image available? Yes
Molecular mass (g mol-1) 416.30
PIN (Preferred Identification Name) rac-(R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
IUPAC name racemate comprising (R)-α-cyano-3-phenoxybenzyl (1S)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS name (R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-rel-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Other status information -
Herbicide Resistance Classification (HRAC) Not applicable
Insecticide Resistance Classification (IRAC) 3
Fungicide Resistance Classification (FRAC) Not applicable
Physical state Colourless crystals
Related substances & organisms

Formulations:
Property Value
Example manufacturers & suppliers of products using this active
  • BASF
  • Certis
Example products using this active
  • Antec
  • Contest
  • Fedona
  • Littac
  • Tenopa
UK LERAP status LERAP Category A
Formulation and application details Available in various formulations including crops sprays and livestock pour-ons .


ENVIRONMENTAL FATE

for alpha-cypermethrin

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 0.004 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 596000 A5 - Toluene -
21300 A5 - Methanol -
584000 A5 - Ethyl acetate -
Melting point (oC) 81.5 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) - - -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 3.16 X 1005 Calculated -
Log P 5.5 A4 High
Bulk density (g ml-1)/Specific gravity 1.33 A5 -
Dissociation constant (pKa) at 25oC 5 Q3 -
Note: Weak acid
Vapour pressure at 25oC (mPa) 0.00034 A5 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 6.90 X 10-02 A5 Non-volatile
Henry's law constant at 20oC (dimensionless) 1.75 X 10-05 Q2 Moderately volatile
GUS leaching potential index -1.18 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 276nm = 2073, 300nm = 38.64 A4 -
Surface tension (mN m-1) - - -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 35 A5 Moderately persistent
DT50 (lab at 20oC) 100 A5 Persistent
DT50 (field) 35 A5 Moderately persistent
DT90 (lab at 20oC) 166 A5 -
DT90 (field) 210 A5 -
Note EU dossier Lab studies DT50 range 25-125 days, DT90 range 102-792 days, field studies DT50 range 14-112 day (UK conditions), DT90 range 35-385 days; Other sources:DT50 77 days (DW4)
Aqueous photolysis DT50 (days) at pH 7 Value - A5 -
Note Very slow degradation by sunlight
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 101 A5 Persistent
Note DT50 sensitive to pH: stable at pH 4, 7.3 days at pH 9
Water-sediment DT50 (days) 21 A5 Fast
Water phase only DT50 (days) 1.3 A5 Moderately fast

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd 577 A5 Non-mobile
Koc 57889
Notes and range EU dossier Kd range 821-1042 mL/g
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
3-phenoxybenzoic acid Soil   0.480   Major fraction, Not relevant


ECOTOXICOLOGY

for alpha-cypermethrin

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 1204 A5 Threshold for concern
CT50 (days) Not available -
Bioaccumulation potential - Calculated High
Mammals - Acute oral LD50 (mg kg-1) 57 A5 Rat High
Mammals - Short term dietary NOEL (mg kg-1) 5 A5 Rat High
(ppm diet) 200 -
Birds - Acute LD50 (mg kg-1) > 2025 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.0028 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.00003 A5 Pimephales promelas -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.0003 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.00003 A5 Daphnia magna -
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) - - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.1 A5 Raphidocelis subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees - Acute 48 hour LD50 (μg bee-1) 0.033 A5 Contact High
Earthworms - Acute 14 day LC50 (mg kg-1) > 100 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 0.256 48 hour, NOER = <0.03 g ha-1
A5 Aphidius rhopalosiphi, adult
Harmful at 1 kg ha-1
Harmful at 0.1 kg ha-1
Harmful at 0.01 kg ha-1
% Effect - - -
Other arthropod (2) LR50 g ha-1 0.02 7 day, NOER = 0.0015 g ha-1
A5 Typhlodromus pyri, protonymph
Harmful at 1 kg ha-1
Harmful at 0.1 kg ha-1
Harmful at 0.01 kg ha-1
% Effect 85 Mortality
Dose: 15 g ha-1
L3 Typhlodromus pyri
Harmful
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.3 kg ha-1, 28 days
-
Mesocosm study data NOEAEC mg l-1 0.000015 A5 Aquatic invertebrates and algae -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for alpha-cypermethrin

General:
Property Value Source/Quality Score/Other Information Interpretation
Mammals - Acute oral LD50 (mg kg-1) 57 A5 Rat High
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 0.593 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.015 A5 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.04 A5 Rat, SF=100 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.01 A5 Dog, 90 day, SF=100 -
Dermal penetration studies (%) 10 A5 -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public -
Occupational Inhalation and dermal routes
Examples of European MRLs (mg kg-1) Value Brassicas, beans (with pods) and peas (with pods): 0.5; Onions, garlic and asparagus: 0.10; Lettuce: 2.0; Cucubits: 0.02; Other vegetables: 0.05; Pomes, plums and cherries: 1.0; Citrus, apricots, nectarines and peaches: 2.0; Canefruit and grapes: 0.5; Barley and oat grains: 0.2; Other cereal grains: 0.05
Note Current May 2007. Limits applies to total of all cypermethrin isomers/enantiomers.
For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

-

-

General human health issues Highly toxic by ingestion

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General IMDG Transport Code is product specific and usually a 6.1 or 3
CLP classification 2013 -
EC Risk Classification T - Toxic: R25
Xn - Harmful: R48/22
Xi - Irritant: R37
N - Dangerous for the environment: R50, R53
EC Safety Classification S2, S36/37/39, S45, S61, S60
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II - Warning - Moderately toxic
UN Number 3349 for active, variable with product, usually 1993, 3077 or 3082
Waste disposal & packaging Packaging Group III (minor danger)


TRANSLATIONS

for alpha-cypermethrin

Language Name
English alpha-cypermethrin
French alphacypermethrine
German alpha-Cypermethrin
Danish alpha-cypermethrin
Italian alfametrina
Spanish alfacipermetrina
Greek -
Slovenian alfa-cipermetrin
Polish alfa-cypermetryna
Swedish alfacypermetrin
Hungarian alphamethrin / alpha cypremethrin
Dutch alfa-cypermethrin

Record last updated: Saturday 28 June 2014
Contact: aeru@herts.ac.uk