gamma-cyhalothrin (Ref: DE 225) ** XDE 225 ** Translations

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SUMMARY

Gamma-cyhalothrin is a broad-spectrum pyrethroid insecticide approvd for use in EU. It has a low aqueous solubility, volatile and, based on its chemical properties, would not be expected to leach to groundwater. It is non-persistent in soil systems and would not normally persist in aqueous systems. It has a high mammalian toxicity and there is some concern regarding its potential to bioaccumulate. It is considered to be a neurotoxicant. It is highly toxic to honey bees and many aquatic organisms and moderately toxic to birds and earthworms.

GENERAL INFORMATION
for gamma-cyhalothrin

Description: A pyrethroid insecticide offering broad-spectrum control of insect pests in a wide range of agricultural crops

Example pests controlled: Sucking and chewing insect pests

Example applications: Corn; Oilseed rape; Cereals

Availability status: Current

Introduction & key dates: Late 1990s, Europe; 2003, Indonesia

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

Status	Approved
Dossier rapporteur/co-rapporteur	UK
Date inclusion expires	31/03/2025

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, Argentina, Chile, China, Indonesia, South Africa, Mexico, Romania, USA

General status:

Pesticide type	Insecticide
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 acting by contact and/or ingestion. Sodium channel modulator, distrupts nerve function
CAS RN	76703-62-3
EC number	-
CIPAC number	768
US EPA chemical code	12887
Chiral molecule	No
Chemical formula	C23H19ClF3NO3
SMILES	C1([C@@H]([C@@H]1\C=C(\C(F)(F)F)Cl)C(=O)O[C@@H](c1cc(ccc1)Oc1ccccc1)C#N)(C)C
International Chemical Identifier key (InChIKey)	ZXQYGBMAQZUVMI-GCMPRSNUSA-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	(S)-α-cyano-3-phenoxybenzyl (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate
CAS name	(S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylate
Other status information	Marine pollutant; PAN Listed as Highly Hazardous Chemical
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	Helicoverpa armigera
Physical state	Off-white coloured solid
Related substances & organisms	-

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Cheminova Dow AgroSciences
Example products using this active	Fighter Trojan Bull Vantex Proaxis Fentrol Corello GF-317
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	Typically formulated as suspension in a solvent.

ENVIRONMENTAL FATE
for gamma-cyhalothrin

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		0.0021	A4	Low
Solubility - In organic solvents at 20oC (mg l-1)		500000	A5 - Acetone	-
		500000	A5 - Ethyl acetate	-
		138000	A5 - Methanol	-
		30700	A5 - Heptane	-
Melting point (oC)		55.6	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		245	A5	-
Flashpoint (oC)		398	A5 - (auto-ignition)	-
Octanol-water partition coefficient at pH 7, 20oC	P	9.12 X 1004	Calculated	-
	Log P	4.96	A5	High
Bulk density (g ml-1)/Specific gravity		1.32	A5	-
Dissociation constant (pKa) at 25oC		-	-	-
		Note:
Vapour pressure at 25oC (mPa)		3.45 X 10-04	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		0.0221	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		3.03 X 10-05	Calculated	Volatile
GUS leaching potential index		-1.11	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		Acidic soln.: 204nm=45600 Neutral soln.: 204nm=45700 Basic soln.: 219nm=29600	-	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	26.8	A5	Non-persistent
	DT50 (lab at 20oC)	26.8	A5	Non-persistent
	DT50 (field)	26.5	A5	Non-persistent
	DT90 (lab at 20oC)	-	-	-
	DT90 (field)	76	A5	-
	Note	EU dossier lab studies DT50 range 16.6-33.8 days; Manufacturers published literature lab studies DT50 28-51 days, Field studies DT50 range 18-30 days, DT90 range 58-94 days; There are a few other literature references available but indications are that DT50 is a few weeks.
Plant matrix DT50 (days)	Value	-	-	-
	Note	-
Aqueous photolysis DT50 (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	136	E4	Persistent
	Note	pH sensitive: stable at pH 5, 1.1 days at pH 9
Water-sediment DT50 (days)		34.5	A5	Moderately fast
Water phase only DT50 (days)		6.4	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	622	A5	Non-mobile
	Koc	59677
	Notes and range	EU dossier Kd range 239-826 mL/g, Koc range 34133-92692 mL/g, soils=4
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

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		Minor fraction
3-phenoxybenzoic acid		Soil		Minor fraction
3-(4-hydroxyphenoxy)benzaldehyde		Soil	0.122	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2-hydroxy-methyl-2-methyl-cyclopropane carboxylic acid	Cyhalothrin compound XI	Animal	-	-
3-(4'-hydroxy)-phenoxy-benzoic acid	Cyhalothrin compound XXIII	Rat (Urinary); Animal	-	-
(Z)-3-(2-chloro-3,3,3-trifluoro-propenyl)-2,2-dimethylcyclo-propane carboxylic acid	Cyhalothrin compound 1a	-	-	-
(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	-	-	-

ECOTOXICOLOGY
for gamma-cyhalothrin

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	2240	A5 (whole fish)	Threshold for concern
	CT50 (days)	9.1		-
Mammals - Acute oral LD50 (mg kg-1)		55	A5 Rat	High
Mammals - Short term dietary NOEL	(mg kg-1)	2	F4 Rat	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Anas platyrhynchos	Low
Birds - Short term dietary (LC50/LD50)		-	-	-
Fish - Acute 96 hour LC50 (mg l-1)		0.000035	A5 Lepomis macrochirus	High
Fish - Chronic 21 day NOEC (mg l-1)		0.00013	P3 Oncorhynchus mykiss	High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.000045	A5 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.0000022	E4 Daphnia magna	High
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		0.000047	A5 Chironomus riparius	High
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		0.000126	A5 Chironomus riparius	High
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		2.85	A5 Pseudokirchneriella subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	0.005	A5	High
	Oral acute 48 hour LD50 (μg bee-1)	4.2	A5	Moderate
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 650	A5 Eisenia foetida, corr	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		0.25	A5 Eisenia foetida, 56 day corr	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	0.23	Mortality A5 Aphidius rhopalosiphi, adult	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	0.0006	Mortality A5 Typhlodromus pyri	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 375g/kg soil	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for gamma-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)		55	A5 Rat	High
Mammals - Dermal LD50 (mg kg-1 body weight)		1643	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		0.028	A5 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.0012	A5 Rat, SF=400 as cyhalothrin	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.0025	A5 Dog, SF=200 as lambda cyhalothrin	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.0003	A5 Rat, SF=1600 as cyhalothrin	-
Dermal penetration studies (%)		2-32%	A5 concentration dependant	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		[LT TWA 8hr: 0.1 mg/m3]	Occupation Exposure	-
Exposure Routes	Public	Acceptable for proposed uses
	Occupational	Acceptable for proposed uses with PPE/PPC
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		Harmful by inhalation Possible liver toxicant

: 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		Not explosive or oxidising
CLP classification 2013		None allocated at this time
EC Risk Classification		T+ - Very toxic: R26 T - Toxic: R25 Xn - Harmful: R21, R43, R48 N - Dangerous for the environment: R50/53
EC Safety Classification		S24, S37, S60
WHO Classification		NL	-	Not listed
US EPA Classification (formulation)		III, IV	-	Caution - Slightly toxic, Caution - Not acutely toxic
UN Number		3082
Waste disposal & packaging		Packging group III (minor danager)

TRANSLATIONS
for gamma-cyhalothrin

Language	Name
English	gamma-cyhalothrin
French	Gamma-cyhalothrine
German	gamma-Cyhalothrin
Danish	gamma-cyhalothrin
Italian	gamma-cialotrina
Spanish	gamma-cihaltrina
Greek	-
Slovenian	gama-cihalotrin
Polish	gamma-cyhalotryna
Swedish	-
Hungarian	-
Dutch	-

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Record last updated: Monday 17 October 2016
Contact: aeru@herts.ac.uk