lambda-cyhalothrin (Ref: OMS 3021) ** PP 321 ** gamma-cyhalothrin ** Translations

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SUMMARY

A synthetic pyrethroid insecticide which is approved for use in the EU. It has a low aqueous solubility, is relatively volatile, is non mobile and, based on chemical properties, there is a low risk of it leaching to ground water. Lambda cyhalothrin is highly toxic to mammals and is a known irritant. It is also highly toxic to fish, aquatic invertebrates and honey bees. It is moderately toxic to earthworms

GENERAL INFORMATION
for lambda-cyhalothrin

Description: A quick-acting insecticide used to control a wide spectrum of agricultural crop and public health pests

Example pests controlled: Aphids; Thrips; Colorado beetles; Caterpillars; Mosquitoes; Ticks; Flies

Example applications: Cotton; Cereals; Potatoes; Hops; Vegetables

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1984, first reported; 1985, introduced Central America and Far East

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	Sweden/Spain
Date inclusion expires	31/03/2023
EU Candidate for substitution (CfS)	Yes - low ADI / ARfD / AOEL; two 'Persistent-Bioaccumulative-Toxic' criteria
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; Russia

Chemical structure:

Isomerism	Lambda-cyhalothrin consists of one enantiomeric pair of isomers and is the more biologically active form of cyhalothrin
Chemical formula	C23H19ClF3NO3
Canonical SMILES	CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(C(F)(F)F)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(/C(F)(F)F)\Cl)C
International Chemical Identifier key (InChIKey)	BFPGVJIMBRLFIR-GUCBCRIZSA-N
International Chemical Identifier (InChI)	InChI=1S/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/b19-12-/t17-,18?,20-/m0/s1
2D structure diagram/image available?	Yes

General status:

Pesticide type	Insecticide
Substance group	Pyrethroid
Minimum active substance purity	810 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Non-systemic, contact and stomach action. Some repellant properties. Sodium channel modulator.
CAS RN	91465-08-6
EC number	415-130-7
CIPAC number	463
US EPA chemical code	128897
PubChem CID	71464055
Molecular mass (g mol-1)	449.85
PIN (Preferred Identification Name)	-
IUPAC name	(R)-a-cyano-3-phenoxybenzyl (1S)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate and (S)-a-cyano-3-phenoxybenzyl (1R)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate
CAS name	(R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-rel-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
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	Aedes aegypti Aphis gossypii Cydia pomonella Meligethes aeneus Thrips tabaci many others
Physical state	Colourless solid
Related substances & organisms	pirimicarb solvent naphtha 1,2-benzisothiazolin-3-one

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	AgriGuard Clayton Syngenta Bayer
Example products using this active	Dovetail Hallmark Seal Z Warrior Jackpot 2 Karate 10CS Molnia
UK LERAP status	Buffer probably required in UK - see product label
Formulation and application details	Often supplied as a suspension that is mixed with water and used as a spray.

ENVIRONMENTAL FATE
for lambda-cyhalothrin

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		0.005	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		500000	A5 - Hexane	-
		500000	A5 - Toluene	-
		250000	A5 - Methanol	-
		250000	A5 - Acetone	-
Melting point (oC)		49.2	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		275	A5	-
Flashpoint (oC)		225	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	3.16 X 1005	Calculated	-
	Log P	5.5	A5	High
Bulk density (g ml-1)/Specific gravity		1.33	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (mPa)		0.0002	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		2.00 X 10-02	A5	Non-volatile
GUS leaching potential index		-3.28	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	High
Maximum UV-vis absorption L mol-1 cm-1		Neutral pH (methanol; 99.0 % w/w): 254nm=1090; 277nm: 2070	A5	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	175	A5	Persistent
	DT50 (lab at 20oC)	175	A5	Persistent
	DT50 (field)	26.9	A5	Non-persistent
	DT90 (lab at 20oC)	1193	A5	-
	DT90 (field)	33.4	A5	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier Lab studies DT50 range 43-1000 days, DT90 range 82 - >5000 days; Field study DT50 range 10.1-47.5 days (Germany), DT90 range 33.6-158 days
Dissipation rate RL50 on plant matrix	Value	2.6	R4	-
	Note	Published literature RL50 range 3.1-93.0 days, 3 field & undercover crops, various matrices, n=4
Dissipation rate RL50 on and in plant matrix	Value	4.9	R4	-
	Note	Published literature RL50 range 0.5-15.3 days, 18 field crops, various matrices, n=28
Aqueous photolysis DT50 (days) at pH 7	Value	40	A3	Stable
	Note	Expected to be negligible in field conditions
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 5.2 and pH 6.9, DT50 ~7 days at pH 9
Water-sediment DT50 (days)		15.1	A5	Fast
Water phase only DT50 (days)		0.24	A5	Fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	3709	A5	Non-mobile
	Koc	283707
	Notes and range	EU dossier Kd range 1245-6890 mL/g, Kfoc range 70100-200000, Soils=14
Freundlich	Kf	4167	A4	Non-mobile
	Kfoc	290311
	1/n	0.966
	Notes and range	EU dossier Kf range 464-33000 mL/g, Kfoc range 47800-1325000, 1/n range 0.85-1.21 mL/g, Soils=14
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
(RS)-alpha-cyano-3-(4-hydroxyphenoxy)benzyl-(Z)-(1RS)-cis-3-(2-chloro-3, 3, 3-trifluoropropenyl)-2, 2-dimethylcyclopropanecarboxylate		Soil	0.121	Major fraction, Relevancy unknown
3-phenoxybenzoic acid		Soil	0.314	Major fraction, Relevant
(Z)-3-(2-chloro-3,3,3-trifluoro-propenyl)-2,2-dimethylcyclo-propane carboxylic acid		Soil	0.359	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
(RS)-á -cyano-3-phenoxy-benzyl alcohol	Cyhalothrin compound III	-	-	-
3-phenoxybenzaldehyde	Cyhalothrin compound IV	-	-	-
(RS)-3-phenoxymandelamide	Cyhalothrin compound IX	-	-	-
3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2-hydroxy-methyl-2-methyl-cyclolambda-propane carboxylic acid	Cyhalothrin compound XI	Animal	-	-
3-(4'-hydroxy)-phenoxy-benzoic acid	Cyhalothrin compound XXIII	Rat (Urinary; Animal	-	-
(1RS)-trans-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethyl-cyclopropane carboxylic acid	Cyhalothrin compound 1b	-	-	-

ECOTOXICOLOGY
for lambda-cyhalothrin

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	4982	A5 (Other literature log BCF range 3.2-3.3 (R3))	Threshold for concern
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		56	A5 Rat	High
Mammals - Short term dietary NOEL	(mg kg-1)	0.7	A5 Rat	High
	(ppm diet)	10		-
Birds - Acute LD50 (mg kg-1)		> 3950	A5 Anas platyrhynchos	Low
Birds - Short term dietary (LC50/LD50)		> 5300 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		0.00021	A5 Lepomis macrochirus	High
Fish - Chronic 21 day NOEC (mg l-1)		0.00025	A5 Oncorhynchus mykiss	High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.00036	A5 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.3	A5 Daphnia magna	Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.000003	F3 Americamysis bahia	High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		0.00016	A5 Chironomus riparius	High
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		0.105	A5 Chironomus riparius	Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		> 0.3	A5 Raphidocelis subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		> 0.31	Q2 Unknown species	Moderate
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	0.038	A5	High
	Oral acute 48 hour LD50 (μg bee-1)	0.91	A5	High
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 500	A5 Eisenia foetida corr	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	0.2	7 day A5 Typhlodromus pyri	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	23	Mortality Dose: 7.5 g ha-1, 28 day A5 Pterostichus melanarius	-
Soil micro-organisms		Nitrogen mineralisation: <-21% effect on ammonification/nitrification Carbon mineralisation: No significant adverse effect	A5 Dose: 1.25 kg ha-1	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for lambda-cyhalothrin

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)		56	A5 Rat	High
Mammals - Dermal LD50 (mg kg-1 body weight)		> 632	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		0.066	A5 Rat, 4 hr (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.0025	A5 Rat, SF=300	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.005	A5 Dog, SF=300	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.00063	A4 Rat, 1 year, SF=300	-
Dermal penetration studies (%)		25	A5 default	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Slight risk of dietary exposure Risk assessment indicates that ARfD may be exceeded in a few commodities
	Occupational	PPE/PPC 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		Harmful if swallowed, inhaled or in contact with skin Possible immune system and thyroid toxicant in susceptable individuals

: 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 variable depending upon product, often either 3 or 9 Not explosive or oxidising
CLP classification 2013		Health: H301, H312, H330 Environment: H400, H410
EC Risk Classification		T+ - Very toxic: R26 T - Toxic: R25; R43 Xn - Harmful: R21 N - Dangerous for the environment: R50, R53
EC Safety Classification		S1/2, S28, S36/37/39, S38, S45, S60, S61
WHO Classification		II	-	Moderately hazardous
US EPA Classification (formulation)		II	-	Warning - Moderately toxic
UN Number		3349 for active, variable with product, usually 1993 or 3082
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for lambda-cyhalothrin

Language	Name
English	lambda-cyhalothrin
French	lambda-cyhalothrine
German	lambda-Cyhalothrin
Danish	lambda-cyhalothrin
Italian	lambda-cialotrina
Spanish	cihalotrin lambda
Greek	-
Slovenian	lambda-cihalotrin
Polish	lambda-cyhalotryna
Swedish	lambda-cyhalotrin
Hungarian	lambda-cyhalothrine
Dutch	lambda-cyhalothrin

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Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk