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PhD Oportunity with Syngenta & the University of Hertfordshire

alpha-cypermethrin (Ref: OMS 3004)
** alphacypermethrin ** alphamethrin ** FMC 63318 ** FMC 39391 ** alfamethrin ** 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 relatively 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. Alpha-cypermethrin is moderately toxic to earthworms.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for alpha-cypermethrin

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

Example pests controlled: Weevils; Moths; Caterpillars; Mites; Bollworm; Budworm; Green mirid; Cutworms; Aphids; Wireworms

Example applications: Asparagus; Brassicas; Cucumber; Leafy crops; Curcubits; OSR; Cereals including barley, wheat, rye, oats, triticale; Ornamentals; Forestry; Public health; Veterinary medicine

Efficacy & activity: Has been shown, via research and field trials, to have a high level of effectiveness for the control of a wide range of insect pests on agricultural crops.

Availability status: Current

Introduction & key dates: 1983, first reported; circa 1985, first introduced

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Belgium/Greece
Date inclusion expires 31/07/2018

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: Australia

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Insecticide, Veterinary substance
Substance group Pyrethroid
Minimum active substance purity 980 g/kg
Known relevant impurities EU dossier - None declared
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, a specific isomer or a derivative 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 key (InChIKey) GUQZCTLEJXHSIH-RZAVTOELSA-N
International Chemical Identifier (InChI) InChI=1S/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
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) 3
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Aphis gossypii
Bemisia tabaci
Helicoverpa armigera
Meligethes aeneus
Bactrocera oleae
Chrysoperla carnea
Halotydeus destructor
Thrips tabaci
Physical state Colourless crystals
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
  • BASF
  • Certis
Example products using this active
  • Antec
  • Contest
  • Fedona
  • Littac
  • Tenopa
UK LERAP status Buffer probably required in UK - see product label
Formulation and application details Available in various formulations including crops sprays and livestock pour-ons .


ENVIRONMENTAL FATE

for alpha-cypermethrin

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) 0.004 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 596000 A5 - Toluene -
21300 A5 - Methanol -
584000 A5 - Ethyl acetate -
Melting point (oC) 82.1 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 248 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 6.31 X 1005 Calculated -
Log P 5.8 A4 High
Bulk density (g ml-1)/Specific gravity - A5 -
Dissociation constant (pKa) at 25oC No dissociation A5 -
Note: Not applicable
Vapour pressure at 25oC (mPa) 0.00038 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 5.30 X 10-02 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -2.00 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 276nm = 2073, 300nm = 38.64 A4 -
Surface tension (mN m-1) Not applicable A4 -

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 Not readily biodegradable
Soil degradation (days) (aerobic) DT50 (typical) 23.0 A4 Non-persistent
DT50 (lab at 20oC) 23.4 A4 Non-persistent
DT50 (field) 42.6 A5 Moderately persistent
DT90 (lab at 20oC) 166 A5 -
DT90 (field) 120.2 A5 -
DT50 modelling endpoint 36.2 A5 normalised, geometric mean -
Note EU 2017 dossier Lab studies DT50 range 3.1-48.1 days - not normalised, DT90 range 4.5-329.4 days, Soils=7, Field studies DT50 range 11.7-114.1 days, DT90 range 38.7-250.5 days, Soils = 6; EU 2004 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)
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value 4.8 R4 -
Note Published literature RL50 range 3.7-7.3 days, 3 field & undercover grown crops, various matrices, n=5
Aqueous photolysis DT50 (days) at pH 7 Value 6.3 A5 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 70 A - @ 25deg C Moderately persistent
Note DT50 sensitive to pH: stable at pH 4, 3.3 days at pH 9 & 25 degC
Water-sediment DT50 (days) 21 A5 Fast
Water phase only DT50 (days) 1.3 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 3308 A5 Non-mobile
Koc 288735
Notes and range EU 2017 dossier Kd range 2366-4362 mL/g, Koc range 228622-353100 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
3-phenoxybenzoic acid Soil   0.054   Major fraction, Relevant
3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid This metabolite may cause environmental pollution, click here for further information Soil   0.136   Major fraction, Relevant
4-hydroxy-alpha-cypermethrin (Ref: CL 194198) Soil   0.08   Major fraction, Relevant


ECOTOXICOLOGY

for alpha-cypermethrin

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) 910 A5 Threshold for concern
CT50 (days) 7.8 -
Mammals - Acute oral LD50 (mg kg-1) 40 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) 0.0018 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.00003 A5 Pimephales promelas High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.00022 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.00003 A5 Daphnia magna High
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) 0.000013 A5 Chironomus riparius High
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) > 0.00139 A5 Lemna gibba High
Non-target plants > 100.0 A5 Onion, Oats, Pea, Rapseed
Vegetative vigour ER50
as g/ha
-
> 100 A5 Onion, Oats, Pea, Rapseed
Emergence ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 0.084 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) 0.033 A5 Apis mellifera High
Oral acute 48 hour LD50 (μg bee-1) 0.059 A5 Apis mellifera 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) > 2.00 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 0.031 Mortality
A5 Aphidius rhopalosiphi
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 0.0019 Mortality
A5 Typhlodromus pyri
-
% Effect 85 Mortality
Dose: 15 g ha-1
L3 Typhlodromus pyri
-
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 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) 40 A5 Rat High
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 1.33 A5 Rat, 4 hr (nose only) -
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 (%) 0.7-3.0 A5 Concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public No unacceptable risks identified for the general public, bystanders and residents
Occupational No unacceptable risks identified for operators or other farm workers
European MRLs Click here for the EU MRL pesticide database
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 Highly toxic by ingestion
USEPA - possible human carcinogen
dy

: 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 IMDG Transport Code is product specific and usually a 6.1 or 3
Not explosive or oxidising
CLP classification 2013 Health: H301, H335, H373
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases T - Toxic: R25
Xn - Harmful: R48/22
Xi - Irritant: R37
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases 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 Click here for a description of UN packaging marks 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: Monday 13 November 2017
Contact: aeru@herts.ac.uk