alpha-cypermethrin (Ref: OMS 3004) |
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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
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 |
EU Candidate for substitution (CfS) | No |
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 |
Also used in: Australia
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 | - | |
Isomerism | 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:
ENVIRONMENTAL FATE
for alpha-cypermethrin
Key metabolites:
Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy ![]() |
|
3-phenoxybenzoic acid | Soil | 0.054 | Major fraction, Relevant | |
3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid ![]() |
Soil | 0.136 | Major fraction, Relevant | |
4-hydroxy-alpha-cypermethrin (Ref: CL 194198) | Soil | 0.08 | Major fraction, Relevant |
ECOTOXICOLOGY
for alpha-cypermethrin
HUMAN HEALTH AND PROTECTION
for alpha-cypermethrin
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) | 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:
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: Thursday 18 January 2018
Contact: aeru@herts.ac.uk