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

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

SUMMARY

Gamma-cyhalothrin is a broad-spectrum pyrethroid insecticide currently being considered for authorisation in the EU. It has a low aqueous solubility, non-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 including both spring and winter cereals

Introduction: Late 1990s, Europe; 2003, Indonesia

EC Regulation 1107/2009 (repealing 91/414):
Status Pending
Dossier rapporteur/co-rapporteur UK
Date inclusion expires -

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

General status:
Pesticide type Insecticide
Substance group Pyrethroid
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 -
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 (InChI) InChI=1/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
Herbicide Resistance Classification (HRAC) Not applicable
Insecticide Resistance Classification (IRAC) 3
Fungicide Resistance Classification (FRAC) Not applicable
Physical state Off-white coloured solid
Related substances & organisms -

Formulations:
Property Value
Example manufacturers of products using this active
  • 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 Non-volatile
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.
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)- -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 2240 A5 (whole fish) Threshold for concern
CT50 (days) 9.1 -
Bioaccumulation potential - Calculated High
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 Moderate
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 -
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 -
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) - - -
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 - Acute 48 hour LD50 (μg bee-1) 0.03 A5 Contact High
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
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 0.0006 Mortality
A5 Typhlodromus pyri
Harmful at 1 kg ha-1
Harmful at 0.1 kg ha-1
Harmful at 0.01 kg ha-1
% 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
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
Examples of European MRLs (mg kg-1) Value -
Note For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

General human health issues Harmful by inhalation
Skin sensitiser
Possible liver toxicant

: 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 Not explosive or oxidising
CLP classification 2013 Danger: H330, H301
Warning: H373, H317
Environment: H400, H410
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 -

Record last updated: Wednesday 12 March 2014
Contact: aeru@herts.ac.uk