| cyhalothrin (Ref: OMS 2011) |
 |
Environmental Fate - Ecotoxicology - Human Health
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Further data may be found in the VSDB
GENERAL INFORMATION 
for cyhalothrin
Description: An insecticide and acaricide used to control crops pests and animal ectoparasites
Example pests controlled: Whitefly; Cutworms; Leafminers; Red spidermite
Example applications: Ornamentals; Apples & pears
Efficacy & activity: -
Availability status: Current
Introduction & key dates: circa 1982, Australia
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | - |
| Date inclusion expires | Expired |
| EU Candidate for substitution (CfS) | Not applicable |
| 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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Chemical structure:
| Isomerism | A chiral molecule that consists of a mixture of four stereoisomers. |
| 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(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C(/C(F)(F)F)\Cl)C |
| International Chemical Identifier key (InChIKey) | ZXQYGBMAQZUVMI-UHFFFAOYSA-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/t17-,18?,20-/m1/s1 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide, Veterinary substance | |||
| Substance group | Pyrethroid | |||
| Minimum active substance purity | - | |||
| Known relevant impurities | - | |||
| Substance origin | Synthetic | |||
| Mode of action | Non-systemic with contact and stomach action. Some repellant properties. Sodium channel modulator. | |||
| CAS RN | 68085-85-8 | |||
| EC number | 268-450-2 | |||
| CIPAC number | 405 | |||
| US EPA chemical code | 128867 | |||
| PubChem CID | 5281873 | |||
| Molecular mass (g mol-1) | 449.85 | |||
| PIN (Preferred Identification Name) | rac-(E)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate | |||
| IUPAC name | (RS)-α-cyano-3-phenoxybenzyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate | |||
| CAS name | cyano(3-phenoxyphenyl)methyl (1R,3R)-rel-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate | |||
| Other status information | PAN Listed as Highly Hazardous Chemical; OSPAR soc; Chemical subject to PIC regulations | |||
| 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 | Aphis gossypii Helicoverpa armigera Spodoptera litura Tribolium castaneum Haematobia irritans many others |
|||
| Physical state | Yellow-brown viscous oil | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically | - | |||
| Example products using this active | - | |||
| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | - | |||
ENVIRONMENTAL FATE
for cyhalothrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.004 | B5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 500000 | L3 - Acetone | - | |
| 500000 | L3 - Methanol | - | ||
| 500000 | L3 - Toluene | - | ||
| 500000 | L3 - Ethyl acetate | - | ||
| Melting point (oC) | Not applicable | Q3 | - | |
| Boiling point (oC) | Decomposes before boiling | L3 | - | |
| Degradation point (oC) | 275 | L3 | - | |
| Flashpoint (oC) | 204 | L3 - (closed cup) | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.31 X 1006 | Calculated | - |
| Log P | 6.8 | B2 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.25 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 9 | L3 | - | |
| Note: Hydrolysis prevents accurate determination | ||||
| Vapour pressure at 20oC (mPa) | 1.00 X 10-09 | B3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.80 X 10-02 | H4 | Non-volatile | |
GUS leaching potential index  |
-2.20 | 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 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 57 | B4 | Moderately persistent |
| DT50 (lab at 20oC) | 57 | B4 | Moderately persistent | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | Lab studies DT50 range 32-82 days | |||
| Dissipation rate RL50 on plant matrix | Value | 5.2 | R4 | - |
| Note | Published literature RL50 range 3.4-10.8 days, 5 field crops, various matrices, n=5 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 4.9 | R4 | - |
| Note | Published literature RL50 range 1.6-10.3 days, 3 field crops, various matrices, n=3 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | Stable | L3 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | - | L3 | - |
| Note | Hydrolysed slowly pH 7 to pH 9, faster at pH 9 | |||
| Water-sediment DT50 (days) | - | - | - | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | H3 | Non-mobile |
| Koc | 180000 | |||
| Notes and range | Best available data | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| (RS)-alpha-amido-3-phenoxybenzyl-(1-RS)-cis,trans-3-(ZE-2-chloro-3,3,3-trifluoro prop-1-enyl)-2,2-dimethylcyclopropanecarboxylate | - | Soil | - | - |
| (1RS)-Cis-3-(2-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-car boxylic acid | - | Soil (Aerobic) | - | - |
| 3-phenoxybenzoic acid (Ref: ) Note: Hydrolysed slowly pH 7 to pH 9, faster at pH 9 |
- | Soil (Aerobic) | - | - |
| 3-phenoxybenzaldehyde | 3-PBAl | Plants; Soil (Aerobic) | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 1950 | Q3 Whole fish | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 140 | B5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 2.4 | B5 Rat | High |
| (ppm diet) | 20 | - | ||
| Birds - Acute LD50 (mg kg-1) | 5000 | B5 Anas platyrhynchos | Low | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.00046 | B4 Lepomis macrochirus | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.38 | F4 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| 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) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | - | - | - | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 0.027 | B5 | High | |
| Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Bumblebees (Bombus spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| - | ||||
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| - | ||||
| Mason bees (Osmia spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Other pollinators (1) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Other pollinators (2) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | R4 Eisenia foetida | Low | |
| 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 | - | - | - |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for 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) | 140 | B5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | 200 | L3 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.086 | L3 Rar, 4 hr | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.005 | A5 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.02 | JMPR 2007 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.0025 | BA5; EU 2001 | - | |
| Dermal penetration studies (%) | 0.3 | BA5; EU 2001 | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
- |
A0; B0; C0; D0; E0 |
|
- |
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- |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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- |
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- |
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| General human health issues | Moderately toxic | |||||||
| Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other : Yes, known to cause a problem  : No, known not to cause a problem  : Possibly, status not identified - : No data found |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Prevent generation of dust | |||
| CLP classification 2013 | Health: H301, H312, H330 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R20, R21, R22 N - Dangerous for the environment: R50 R53 |
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| EC Safety Classification |
S13, S60, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| UN Number | 3352 | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | cyhalothrin |
| French | cyhalothrine |
| German | Cyhalothrin |
| Danish | cyhalothrin |
| Italian | cialotrina |
| Spanish | cihalotrina |
| Greek | - |
| Slovenian | cihalotrin |
| Polish | cyhalotryna |
| Swedish | - |
| Hungarian | cihalotrin |
| Dutch | - |
Record last updated: Friday 28 June 2019
Contact: aeru@herts.ac.uk