| gamma-cyhalothrin (Ref: DE 225) |
 |
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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
Efficacy & activity: -
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 |
| 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 |
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Also used in: Australia, Argentina, Chile, China, Indonesia, South Africa, Mexico, Romania, USA
Chemical structure:
| Isomerism | Cyhalothrin is a molecule with 3 chiral centres. Gamma-cyhalothrin is considered to be the most insecticidally active isomer. |
| 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) | 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 |
| 2D structure diagram/image available? | Yes |
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 | |||
| PubChem CID | 6440554 | |||
| 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 | |||
| 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 | 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 |
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| Example products using this active |
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| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| 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 20oC (mPa) | 3.45 X 10-04 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 0.0221 | A5 | Non-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 |
General biodegradability | - |
| 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 | - | |
| DT50 modelling endpoint | - | - | - | |
| 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. | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | 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 | 1107/2009 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 days 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 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| 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 dependent | - | |
| 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 Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Harmful by inhalation Possible liver toxicant |
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: 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 |
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| 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: Thursday 23 August 2018
Contact: aeru@herts.ac.uk