lambda-cyhalothrin (Ref: OMS 3021) ** PP 321 ** 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 not 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 pests including aphids, Colarado beetle and thrips

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

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

Status	Approved
Dossier rapporteur/co-rapporteur	Sweden
Date inclusion expires	31/12/2015

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
Substance group	Pyrethroid
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	-
Chiral molecule	No
Chemical formula	C23H19ClF3NO3
SMILES	Cl\C(=C/[C@H]3[C@@H](C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C)C(F)(F)F
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
Structure diagram/image available?	Yes
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	-
Herbicide Resistance Classification (HRAC)	Not applicable
Herbicide Resistance Classification (WSSA)	Not applicable
Insecticide Resistance Classification (IRAC)	3
Fungicide Resistance Classification (FRAC)	Not applicable
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	AgriGuard Clayton Syngenta Bayer
Example products using this active	Dovetail Hallmark Seal Z Warrior Jackpot 2 Karate 10CS
UK LERAP status	LERAP Category A, LERAP Category B, Broadcast Air Assisted LERAP (depending on situation)
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 25oC (mPa)		0.0002	A5	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		2.00 X 10-02	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		7.38 X 10-06	K3	Moderately 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
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	-
	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
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	Very persistent
	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	91/414 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
(1RS)-trans-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethyl-cyclopropane carboxylic acid	Cyhalothrin compound 1b	-	-	-
(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	-	-

ECOTOXICOLOGY
for lambda-cyhalothrin

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	4982	A5 (Other literature log BCF range 3.2-3.3 (R3))	Threshold for concern
	CT50 (days)	Not available		-
Bioaccumulation potential		-	Calculated	High
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	-
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	-
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)		-	-	-
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)	-	-	-
	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	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	-	-	-
	% Effect	23	Mortality Dose: 7.5 g ha-1, 28 day A5 Pterostichus melanarius	Harmless
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
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	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.0006	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
Examples of European MRLs (mg kg-1)	Value	Lettuce: 1.0; Eggplants and strawberries: 0.5; Celery: 0.3; Cabbages, beans (with pods), peas (with pods), grapes, nectarines, peaches, lemons, limes and manadarins: 0.2; Broccoli, sweet peppers, tomatoes, summer squash, cauliflowers, cucumbers, grapefruit, currants, gooseberries, pome fruit and other stone fruit: 0.1; Brussel sprouts, melons (not watermelons), winter squash, pumpkins and barley grains: 0.05; Other vegetables, other fruit, beans (edible part), peas (edible part) and other cereal grains: 0.02
	Note	Current May 2007. 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		Harmful if swallowed, inhaled or in contact with skin Possible immune system and thyroid toxicant in susceptable individuals Skin sensitiser

: 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 variable depending upon product, often either 3 or 9 Not explosive or oxidising
CLP classification 2013		Danger: H410, H330, H317, H312, H301 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: Friday 09 January 2015
Contact: aeru@herts.ac.uk