Bifenthrin (Ref: FMC 54800) |
![]() Last updated: 12/01/2021 |
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(Also known as: bifenthrine; biphenthrin; biphentrin; biphenate) |
SUMMARY |
Bifenthrin is a pyrethroid insecticide used to control a range of pests. It has a low aqueous solubility and is volatile. There is a low risk of groundwater contamination based on its chemical properties and it is not persistent in soil. There are some concerns about bioaccumulation and the pesticide shows a high oral toxicity to mammals as well as being an endocrine distupter and a neurotoxicant. It is toxic to birds, most aquatic organisms, honeybees and earthworms. |
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A broad spectrum pyrethroid acaricide/insecticide for use in a wide range of crops to control sucking and biting foliar pests | |
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Fire ants; Blue grass weevil; Armyworms; Cutworms; centipedes; Crickets; earwigs; Millipedes; Sowbugs; Mole crickets; Ticks; Fleas; Grasshoppers | |
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Non-cropped situations including lawns, athletic fields, ornamentals, residences and commercial buildings | |
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- | |
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Current | |
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circa 1984 |
UK regulatory status |
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Not approved | ||
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Expired | ||
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Buffer probably required in UK - see product label |
EC Regulation 1107/2009 (repealing 91/414) |
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Not approved | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Belgium/Hungary | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Expired | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Not applicable | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Yes | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Also used in |
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Australia, USA |
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Chemical structure |
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Bifenthrin is chiral molecule and is a mixture of the Z-isomer (~99.7%) and the E-isomer (~0.3%). | |
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C₂₃H₂₂ClF₃O₂ | |
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CC1=C(C=CC=C1COC(=O)C2C(C2(C)C)C=C(C(F)(F)F)Cl)C3=CC=CC=C3 | |
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CC1=C(C=CC=C1COC(=O)[C@@H]2[C@@H](C2(C)C)/C=C(/C(F)(F)F)\Cl)C3=CC=CC=C3 | |
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OXCDWLBJSLVWHB-LKRLXIKPSA-N | |
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InChI=1S/C23H22ClF3O2/c1-14-16(10-7-11-17(14)15-8-5-4-6-9-15)13-29-21(28)20-18(22(20,2)3)12-19(24)23(25,26)27/h4-12,18,20H,13H2,1-3H3/b19-12- | |
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Yes |
General status |
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Insecticide, Acaricide | |
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Pyrethroid | |
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930 g kg⁻¹ | |
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EU dossier - Toluene <5 g kg⁻¹ | |
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Synthetic | |
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Contact and stomach action with some residual effect. Sodium channel modulator. | |
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82657-04-3 | |
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- | |
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415 | |
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128825 | |
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6442842 | |
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422.88 | |
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rac-(2-methyl[1,1'-biphenyl]-3-yl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate | |
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2-methyl-3-phenylbenzyl (1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate | |
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(2-methyl(1,1'-biphenyl)-3-yl)methyl (1R,3R)-rel-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate | |
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- | |
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- | |
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Not applicable | |
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Not applicable | |
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3A | |
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Not applicable | |
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Bemisia argentifolii, Frankliniella occidentalis, Plutella xylostella, Tetranychus turkestani, plus others | |
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Off-white waxy solid | |
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Formulations |
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Often supplied as a soluble or emulsifiable concentrate which is mixed with water and applied as a spray |
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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 ) 5 = Verified data used for regulatory purposes |
Low | ||||||||
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735700 | 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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144500 | 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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48000 | 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 ) Methanol5 = Verified data used for regulatory purposes |
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556300 | 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 ) Xylene5 = Verified data used for regulatory purposes |
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79.6 | 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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Decomposes before boiling | 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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280 | 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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151 | L3 L = Pesticide manuals and hard copy reference books / other sources (closed cup)3 = Unverified data of known source |
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3.98 X 1006 | Calculated | - | |||||||
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6.6 | 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 |
High | ||||||||
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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 ) 5 = Verified data used for regulatory purposes |
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Not applicable | H3 H = The US ARS pesticide properties database (click here ) 3 = Unverified data of known source |
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No dissociation | |||||||||||
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0.0178 | 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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7.74 X 10-05 | 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 |
Non-volatile | ||||||||
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All pH's: 250nm = 3282.9, sigificant absorption 290-300nm | 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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Degradation |
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26 | Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source |
Non-persistent | |||||||
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102.2 | 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 |
Persistent | ||||||||
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86.8 | 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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346.5 | 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 ) 5 = Verified data used for regulatory purposes |
Persistent | ||||||||
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3410.8 | 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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EU dossier lab studies DT₅₀ range 54.2-173.7 days, DT₉₀ range 223-577 days, field studies DT₅₀ range 5.4-267 days, DT₉₀ range 135.3-965.2 days; Other studies DT₅₀ (1) range 65-125 days, (2) range 2-6 months depending on soil type. | ||||||||||
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6.1 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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Published literature RL₅₀ range 1.3-27.0 days, 5 field & undercover grown crops, various matrices, n=6 | ||||||||||
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4.5 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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Published literature RL₅₀ range 0.8-14.0 days, 11 field & undercover grown crops, various matrices, n=20 | ||||||||||
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12 | B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes |
Moderately fast | |||||||
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DT₅₀: 255 days in natural sunlight, 12 days in artifical light | ||||||||||
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Stable | 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 |
Stable | |||||||
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Stable pH 5 to pH 9 at 25 °C. Hydrolysis occurs at elevated temperatures e.g. DT₅₀ 20 mins at pH 4, 90 °C | ||||||||||
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161 | 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 |
Slow | ||||||||
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8 | K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data |
Moderately fast |
Soil adsorption and mobility |
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3567 | 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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236610 | ||||||||||
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EU dossier Kd range 992-5429 mL g⁻¹, Koc range 130526-301611 mL g⁻¹, Soils=4 | ||||||||||
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No |
Fate indices |
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-2.66 | Calculated | Low leachability | ||||||||||||||||||||||||||
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5.35 X 10-03 | Calculated | - | |||||||||||||||||||||||||
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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 | ||||||||||||||||||||||||||||
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Medium | Calculated | - | ||||||||||||||||||||||||||
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Non-mobile | Calculated | - |
Key metabolites |
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Soil | 0.116 | Major fraction, Relevant |
Other known metabolites |
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(2-methylbiphenyl-3-yl)methyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2-(hydroxymethyl)-2-methylcyclopropanecarboxylate | OH-methyl bifenthrin | Animal; Hens (eggs); Soil | - | - | |||||
(4'-hydroxy-2-methylbiphenyl-3-yl)methyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylate | 4'-OH bifenthrin | (a) Sediment; (b) Soil | b=0.08 | - | |||||
2-methyl-3-phenylbenzoic acid | BP acid | Plant; Animal; Soil | - | - | |||||
2-methyl-3-phenylbenzyl alcohol | BP alcohol | Plant; Soil; Water | - | - |
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1703 | E4 E = Manufacturers safety data sheets 4 = Verified data |
Threshold for concern | |||||||
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Not available | - | |||||||||
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54.5 | 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 ) Rat5 = Verified data used for regulatory purposes |
High | ||||||||
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> 5 | B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) Rat5 = Verified data used for regulatory purposes |
High | |||||||
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> 100 | - | |||||||||
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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 ) Rat Reproductive NOAEL5 = Verified data used for regulatory purposes |
High | ||||||||
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1800 | 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 |
Moderate | ||||||||
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4450 mg kg feed⁻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 ) Colinus virginianus5 = Verified data used for regulatory purposes |
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6.63 | 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 ) Colinius virginianus NOED5 = Verified data used for regulatory purposes |
High | ||||||||
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0.00026 | 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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0.000012 | 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 ) Salmo gardneri5 = Verified data used for regulatory purposes |
High | ||||||||
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0.00011 | 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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0.0000013 | 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 magna LOEC5 = Verified data used for regulatory purposes |
High | ||||||||
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0.0000012 | 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 ) Americamysis bahia5 = Verified data used for regulatory purposes |
High | ||||||||
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0.00032 | 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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0.822 | 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 ) Scenedemus subspicatus5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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10 | Q2 Q = Miscellaneous internet resources Unknown species2 = Unverified data of unknown source |
Low | ||||||||
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0.016 | A4 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 mellifera4 = Verified data |
High | |||||||
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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 ) Apis mellifera5 = Verified data used for regulatory purposes |
High | ||||||||
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0.36 | R3 R = Peer reviewed scientific publications Bombus terrestris3 = Unverified data of known source |
High | |||||||
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0.34 | R3 R = Peer reviewed scientific publications Bombus terrestris3 = Unverified data of known source |
High | ||||||||
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0.006 | R4 R = Peer reviewed scientific publications Megachile rotundata4 = Verified data |
High | |||||||
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Contact | ||||||||||
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> 8.0 | 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 |
High | ||||||||
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1.065 | 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 56 days corr5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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100 | Mortality [Dose: 60g ha⁻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 ) Aphidius rhopalosiphi5 = Verified data used for regulatory purposes |
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0.113 | 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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100 | Mortality [Dose: 60g ha⁻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 ) Typhlodromus pyri5 = Verified data used for regulatory purposes |
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Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
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: 0.128 mg kg⁻¹ |
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0.000015 | 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 ) Gammarids copepods & chaoboridae5 = Verified data used for regulatory purposes |
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General |
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High (class III) | - | - | ||||||||
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54.5 | 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 ) 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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1.01 | 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 4 hr5 = Verified data used for regulatory purposes |
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0.015 | 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=1005 = Verified data used for regulatory purposes |
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0.03 | 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 ) Rat SF=1005 = Verified data used for regulatory purposes |
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0.0075 | 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=1005 = Verified data used for regulatory purposes |
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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 ) 5 = Verified data used for regulatory purposes |
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List II | - | - | ||||||||
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Bystanders should not access orchards or vineyards during spraying | |||||||||
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Some risk identified especially during orchard spraying - PPE advised | ||||||||||
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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 ) EU Dir 89/778/EC limit; Calc MAC=45.0 µg l⁻¹5 = Verified data used for regulatory purposes |
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Health issues |
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May cause tremors and staggered gait USEPA - possible human carcinogen |
Handling issues |
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Not explosive or oxidising IMDG Transport Code is usually 9 |
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Health: H300, H317, H331, H351, H372 Environment: H400, H410 |
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Carcinogen category 3: R40 T - Toxic: R25, R23 Xn - Harmful: R22, R48 N - Dangerous for the environment: R50, R53 |
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- | |||
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II (Moderately hazardous) | |||
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3349 | |||
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Packaging Group III (minor danger) |
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bifenthrin | ||
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bifenthrine | ||
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Bifenthrin | ||
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bifenthrin | ||
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bifentrin | ||
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bifentrin | ||
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- | ||
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bifentryna | ||
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- | ||
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bifenthrin | ||
|
- |
Record last updated: | 12/01/2021 |
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 |