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

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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	31/07/2019
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

Also used in: Australia

Chemical structure:

Isomerism	Cypermethrin itself is a chiral molecule and consists of eight isomers, four cis and four trans. Alpha-Cypermethrin contains more than 90% of the insecticidally most active enantiomer pair of the four cis isomers of cypermethrin as
Chemical formula	C22H19Cl2NO3
Canonical SMILES	CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)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(Cl)Cl)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
2D structure diagram/image available?	Yes

General status:

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	-
PubChem CID	3086172
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	-
Relevant Environmental Water Quality Standards	UK Environment Agency non-statutory standard for the protection of aquatic life in freshwater and saltwater annual average 0.0002 ug/L, max acceptable conc 0.002 ug/L UK statutory standard for water quality: ‘Good’ for fresh, transitional & saltwater: 0.1 ng/L as annual mean conc, 0.4 ng/L 95th percentile
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	flufenoxuron propylene glycol cypermethrin beta-cypermethrin zeta-cypermethrin

Formulations:

Property	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		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)		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		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (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		-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	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)		Not applicable	A4	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
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
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

Property		Value	Source/Quality Score/Other Information	Interpretation
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 Seedling 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		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	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
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 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		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		Value	Source/Quality Score/Other Information	Interpretation
General		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		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

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Record last updated: Thursday 27 September 2018
Contact: aeru@herts.ac.uk