Zeta-cypermethrin (Ref: FMC 56701) |
Last updated: 31/07/2024 |
(Also known as: zetacypermethrin; z-cypermethrin ; F 56701) |
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An insecticide used to control beetles, aphids and Lepidoptera in a range of crops | |
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Current | |
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1984, introduced | |
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Approval status |
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Chemical structure |
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Cypermethrin is a chiral molecule and consists of eight isomers, four cis and four trans. Zeta-cypermethrin is a mixture of stereoisomer pairs | |
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C₂₂H₁₉Cl₂NO₃ | |
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CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C | |
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CC1(C(C1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C | |
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KAATUXNTWXVJKI-QPIRBTGLSA-N | |
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InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3 | |
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Yes |
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Common Name | Relationship | Link |
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zeta-cypermethrin | - |
General status |
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Pyrethroid insecticide; Pyrethroid ester insecticide | |
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850 g kg⁻¹ | |
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EU dossier - toluene <2g kg⁻¹, tars 12.5 g kg⁻¹ | |
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Synthetic | |
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Contact and stomach action. Acts mainly on the nervous system. Sodium channel modulator. | |
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97955-44-7 | |
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257-842-9 | |
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733 | |
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109702/129064 | |
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12617362 | |
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No data found | |
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416.31 | |
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mixture of the stereoisomer pairs (S)-cyano(3-phenoxyphenyl)methyl (1R*,3R*)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate and (S)-cyano(3-phenoxyphenyl)methyl (1R*,3S*)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in the ratio range 45–55 to 55–45 respectively | |
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mix of (S)-α-cyano-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate | |
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(S)-cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate | |
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UK Environment Agency non-statutory standard for the protection of aquatic life in freshwater and saltwater annual average 0.0002 µg l⁻¹, max acceptable conc 0.002 µg l⁻¹ UK statutory standard for water quality: ‘Good’ for fresh, transitional & saltwater: 0.1 ng l⁻¹ as annual mean conc, 0.4 ng l⁻¹ 95th percentile |
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Pale yellow viscous liquid | |
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Formulations |
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0.039 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Low | ||||||||
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40120 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) n-Heptane5 = Verified data used for regulatory purposes |
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1000000 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) p-Xylene5 = Verified data used for regulatory purposes |
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1000000 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Acetone5 = Verified data used for regulatory purposes |
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1000000 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Ethyl acetate5 = Verified data used for regulatory purposes |
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-3 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
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360 | A3 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 3 = Unverified data of known source |
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181 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
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3.98 X 1006 | Calculated | - | |||||||
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6.6 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) (EU dossier: LogP 5-6 at pH 2 24 °C; A4)3 = Unverified data of known source |
High | ||||||||
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1.24 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
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Not applicable | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
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No dissociation | |||||||||||
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2.53 X 10-04 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Low volatility | ||||||||
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2.31 X 10-03 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Non-volatile | ||||||||
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Neutral solution: 278nm = 2468, 290nm = 765 Acidic solution 278nm = 2472, 290nm = 765 Basic solution: hydrolysis product formed with maxima = 308 nm |
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
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59.5 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) at 25°C 90% soln5 = Verified data used for regulatory purposes |
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Degradation |
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49 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Moderately persistent | |||||||
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60 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Moderately persistent | ||||||||
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10 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Non-persistent | ||||||||
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56.7 | A3 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 3 = Unverified data of known source |
Moderately persistent | ||||||||
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Earlier EU dossier lab studies DT₅₀ range 6-105 days (A3), DT₉₀ range 34-80.5 days, Current dossier field studies DT₅₀ 6-24 days S. France, Italy and Germany;Other data source: 14 days (DW4) | ||||||||||
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3.05 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Moderately fast | |||||||
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25 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Non-persistent | |||||||
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pH sensitive: Stable at pH 4, variable at pH 9 | ||||||||||
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2 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Fast | ||||||||
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0.1 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Fast | ||||||||
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Soil adsorption and mobility |
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1033 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Non-mobile | |||||||
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121786 | ||||||||||
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1.30 | ||||||||||
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EU dossier Kf range 416-1897 mL g⁻¹, Kfoc range 18326-285562 mL g⁻¹, 1/n range 1.15-1.47, Soils=4 | ||||||||||
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Fate indices |
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-1.09 | Calculated | Low leachability | ||||||||||||||||||||||||||
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356 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Whole fish5 = Verified data used for regulatory purposes |
Threshold for concern | |||||||||||||||||||||||||
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1.2 | - |
Known soil metabolites |
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Major fraction | 0.242 | - | |||||
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Minor fraction | 0.084 | - |
Known groundwater metabolites |
None
Other known metabolites |
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(3-phenoxyphenyl)methanol | mPBAcohol | Plant; Animal | - | ||||
3-phenoxybenzaldehyde | mPBAldehyde | Plant | - |
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Terrestrial ecotoxicology |
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86 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
High | ||||||||
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22 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat Reproductive NOAEL5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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> 5124 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Anas platyrhynchos5 = Verified data used for regulatory purposes |
Low | ||||||||
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> 601 mg kg bw⁻¹ day⁻¹ | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Anas platyrhynchos5 = Verified data used for regulatory purposes |
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2.15 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Colinus virginianus5 = Verified data used for regulatory purposes |
High | ||||||||
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37.5 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Eisenia foetida corr5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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Nitrogen mineralisation: No significant adverse effect at 59 days Carbon mineralisation: No significant adverse effect at 64 days |
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes Dose: 2 mg kg⁻¹ soil |
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> 100 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Ryegrass5 = Verified data used for regulatory purposes Vegetative vigour, EC₅₀ as mg kg⁻¹ soil dw |
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> 100 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Ryegrass5 = Verified data used for regulatory purposes Seedling emergence, ER₅₀ as mg kg⁻¹ soil dw |
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0.002 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Apis mellifera5 = Verified data used for regulatory purposes |
High | |||||||
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0.044 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Apis mellifera5 = Verified data used for regulatory purposes |
High | ||||||||
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5.48 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Aphidius rhopalosiphi Adult5 = Verified data used for regulatory purposes |
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23.18 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Typhlodromus pyri5 = Verified data used for regulatory purposes |
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Aquatic ecotoxicology |
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0.00069 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Oncorhynchus mykiss5 = Verified data used for regulatory purposes |
High | ||||||||
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0.000585 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Oncorhynchus mykiss5 = Verified data used for regulatory purposes |
High | ||||||||
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0.00014 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Daphnia magna5 = Verified data used for regulatory purposes |
High | ||||||||
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0.00001 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Daphnia magna5 = Verified data used for regulatory purposes |
High | ||||||||
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0.0128 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Americamysis bahia3 = Unverified data of known source |
High | ||||||||
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0.001 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Chironomus riparius5 = Verified data used for regulatory purposes |
High | ||||||||
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> 1 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Pseudokirchneriella subcapitata5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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General |
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High (class III) | - | - | ||||||||
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86 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
High | ||||||||
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2000 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
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1.26 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
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0.04 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Dog SF=2005 = Verified data used for regulatory purposes |
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0.125 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat SF=1005 = Verified data used for regulatory purposes |
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0.02 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Dog SF=4005 = Verified data used for regulatory purposes |
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No unacceptable risks to bystanders identified | |||||||||
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Possible risk of exposure to operators or other workers identified - PPE/PPC advised | ||||||||||
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Health issues |
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US EPA - possible human carcinogen |
Handling issues |
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Not explosive or oxidising IMDG Transport Hazard Class 6.1 |
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Health: H302, H317, H332 Environment: H410 |
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II (Moderately hazardous) | |||
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UN2902 | |||
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Packaging Group III (minor danger) | |||
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zeta-cypermethrin | ||
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zetacypermethrine | ||
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zeta-Cypermethrin | ||
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zeta-cypermethrin | ||
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zeta-cipermetrina | ||
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zeta-cipermetrin | ||
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zeta-cypermetryna | ||
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zeta-cypermethrin | ||
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Record last updated: | 31/07/2024 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |