Fenamiphos (Ref: BAY 68138) |
![]() Last updated: 19/01/2021 |
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(Also known as: phenamiphos; methaphenamiphos; SRA 3886) |
SUMMARY |
Fenamiphos is an organophosphorous pesticide that is currently approved for use in the EU. It is moderately soluble in water, has a low volatility and would not normally, based on its chemical properties, be expected to leach to groundwater. It is not normally persistent in soil or water systems. It is highly toxic to mammals, a cholinesterase inhibitor and a neurotoxicant. It shows moderate to high toxicity to most fauna and flora. |
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An insecticide and nematicide used to control ecoparasitic, endoparasitic, free-living and cyst-forming nematodes | |
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Nematodes, Thrips | |
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Fruit including citrus, grapes and pineapples; Glasshouse crops including tomatoes, peppers;, aubergine, cucumber, zucchini; Vegetables; Peanuts; Tobacco; Turf; Ornamentals including herbaceous plants and nursery stock | |
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Efficacy demonstrated by long term use across the EU and in other countries. | |
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Current | |
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1967, first reported; 1968, first introduced; first registered in the United States in 1972 |
UK regulatory status |
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Not approved | ||
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Expired | ||
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No UK approval for use |
EC Regulation 1107/2009 (repealing 91/414) |
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Not approved | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Greece/Cyprus | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Expired | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Yes - low ADI / ARfD / AOEL | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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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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A chiral molecule, fenamiphos is an isomeric mixture of the R- and S-enantiomers | |
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C₁₃H₂₂NO₃PS | |
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CCOP(=O)(NC(C)C)OC1=CC(=C(C=C1)SC)C | |
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No data | |
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ZCJPOPBZHLUFHF-UHFFFAOYSA-N | |
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InChI=1S/C13H22NO3PS/c1-6-16-18(15,14-10(2)3)17-12-7-8-13(19-5)11(4)9-12/h7-10H,6H2,1-5H3,(H,14,15) | |
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Yes |
General status |
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Nematicide | |
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Organophosphate | |
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940 g kg⁻¹ | |
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EU dossier - None declared | |
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Synthetic | |
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Systemic, contact action, absorbed through roots | |
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22224-92-6 | |
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244-848-1 | |
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692 | |
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100601 | |
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31070 | |
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303.36 | |
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(E)-[ethyl 3-methyl-4-(methylsulfanyl)phenyl propan-2-ylphosphoramidate] | |
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(RS)-(ethyl 4-methylthio-m-tolyl isopropylphosphoramidate) | |
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ethyl 3-methyl-4-(methylthio)phenyl (1-methylethyl)phosphoramidate | |
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Potential groundwater contaminant; Marine Pollutant | |
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- | |
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Not applicable | |
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Not applicable | |
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1B | |
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Not applicable | |
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- | |
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Colourless crystals to tan waxy solid depending on purity |
Formulations |
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Often supplied as a capsule suspension that is diluted with water and applied by drip irrigation or via a spray followed by incorporation into the soil |
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345 | 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 |
Moderate | ||||||||
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27000 | 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-Hexane5 = Verified data used for regulatory purposes |
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250000 | 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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250000 | 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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250000 | 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 ) Dichloromethane5 = Verified data used for regulatory purposes |
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46 | 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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200 | 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 expected to self ignite; Not highly flammable | 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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2.00 X 1003 | Calculated | - | |||||||
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3.3 | 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 ) 4 = Verified data |
High | ||||||||
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1.19 | 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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0.067 | 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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2.80 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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In acetoniltrile: 251nm=11738, 290nm=1531 | 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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47.2 | 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 ) at 20 °C5 = Verified data used for regulatory purposes |
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Degradation |
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0.90 | 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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0.9 | 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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1.8 | 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 |
Non-persistent | ||||||||
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3.51 | 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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EU 2017 dossier lab studies DT₅₀ range 0.366-2.01 days, DT₉₀ range 1.28-7.06 days, Soils=4; EU 2006 dossier field studies DT₅₀ range 1.5-2.2 days; Other sources: 50 days (DW3) | ||||||||||
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6.5 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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Published literature RL₅₀ range 6.3-6.7 days, 2 field crops, various matrices, n=2 | ||||||||||
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0.2 | 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 ) 4 = Verified data |
Fast | |||||||
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304 | 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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pH sensitive: 252 days at pH 5, 236 days at pH 9 all at 20 °C | ||||||||||
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60.2 | 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 ) 4 = Verified data |
Moderately fast | ||||||||
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5.8 | 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 ) 4 = Verified data |
Moderately fast |
Soil adsorption and mobility |
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10.1 | 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 |
Moderately mobile | |||||||
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446.2 | ||||||||||
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EU 2017 dossier Kd range 4.2-23.0 mL g⁻¹, Koc range 124-878 mL g⁻¹, Soils=5 | ||||||||||
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1.86 | 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 ) 5 = Verified data used for regulatory purposes |
Moderately mobile | |||||||
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125.2 | ||||||||||
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0.92 | ||||||||||
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EU 2017 dossier Kf range 0.79-3.4 mL g⁻¹, Kfoc range 43.8-240.9 mL g⁻¹, 1/n range 0.85-0.92, Soils=8 | ||||||||||
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None |
Fate indices |
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0.49 | Calculated | Low leachability | ||||||||||||||||||||||||||
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1.08 X 10-03 | Calculated | - | |||||||||||||||||||||||||
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Low | Calculated | - | ||||||||||||||||||||||||||
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Moderately mobile | Calculated | - |
Key metabolites |
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Soil | 0.772 | Major fraction, Relevant | |||||
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Soil | 0.293 | Major fraction, Relevant | |||||
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Soil | 0.065 | Minor fraction, Relevant | |||||
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Soil | 0.251 | Major fraction, Relevant | |||||
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Soil | 0.082 | Minor fraction, Relevant |
Other known metabolites |
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ethyl 3-methyl-4-(methylthio)phosphoramidic acid phenyl ester | des-isopropyl fenamiphos; fenamiphos metabolite M06 | unknown | - | - | |||||
Ethyl 3-methyl-4-(methylsulfinyl)phosphoric acid phenyl ester | des-isopropylamino fenamiphos sulfoxide; fenamiphos metabolite M09 | unknown | - | - | |||||
- | fenamiphos sulfonic acid | Water (Photolysis) | - | - | |||||
4-hydroxy-2-methylbenzenesulfonic acid | fenamiphos phenol sulfonic acid; fenamiphos metabolite M24 | Water (Photolysis); Rat | - | - | |||||
3-methyl-4-(methylthio)phenol | fenamiphos phenol; fenamiphos metabolite M11 | Rat | - | - |
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110 | 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 |
Threshold for concern | |||||||
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0.22 | - | |||||||||
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> 6.0 | 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 ) Rat5 = Verified data used for regulatory purposes |
High | ||||||||
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> 0.3 | 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 ) Rat5 = Verified data used for regulatory purposes |
High | |||||||
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0.8 | 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 ) Colinus virginianus5 = Verified data used for regulatory purposes |
High | ||||||||
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> 43 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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0.0093 | 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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0.0038 | 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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0.0011 | 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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0.01 | 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 ) Daphnia magna4 = Verified data |
Moderate | ||||||||
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0.0057 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) Americamysis bahia3 = Unverified data of known source |
High | ||||||||
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0.01 | 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 ) Chironomus riparius emergence4 = Verified data |
Moderate | ||||||||
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3.8 | 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 ) Scenedemus subspicatus5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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0.28 | 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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0.45 | 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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1.59 | 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 ) Bombus terrestris5 = Verified data used for regulatory purposes |
Moderate | |||||||
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888 | 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 foetida5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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0.49 | 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 ) Eisenia foetida3 = Unverified data of known source |
Moderate | ||||||||
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0.175 | 48 hour 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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1.7 | 7 day 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 pyri protonymph5 = Verified data used for regulatory purposes |
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Nitrogen mineralisation: >25% 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: 133 mg kg⁻¹ soil 28 days |
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0.0035 | 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 ) Fish and aquatic invertebrates5 = Verified data used for regulatory purposes |
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General |
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High (class III) | - | - | ||||||||
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> 6.0 | 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 ) Rat5 = Verified data used for regulatory purposes |
High | ||||||||
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72.0 | 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 ) Rat5 = Verified data used for regulatory purposes |
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0.065 | 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 ) Rat 4 hr (aerosl)5 = Verified data used for regulatory purposes |
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0.0006 | 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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0.0025 | 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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0.0008 | 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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1.0-5.0 | 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 ) concentration dependent5 = Verified data used for regulatory purposes |
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List I; List II | - | - | ||||||||
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Negligible risk to bystanders | |||||||||
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Negligible risk to operators | ||||||||||
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Health issues |
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Toxic by inhalation and skin contact Exposure may be fatal due to respiratory failure May overstimulate the nervous system causing nausea, dizziness and confusion Inhibition of erythrocyte ChE activity |
Handling issues |
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Not explosive or oxidising IMDG Transport Code is usually 6.1 |
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Health: H300, H310, H319, H330 Environment: H400, H410 |
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T+ - Very toxic: R28 T - Toxic: R24 N - Dangerous for the environment: R50, R53 |
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S1/2, S23, S28, S36/37, S45, S60, S61 | |||
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Ib (Highly hazardous / Highly hazardous) | |||
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2783 | |||
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Packaging Group I (great danger) |
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fenamiphos | ||
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phenamiphos | ||
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Fenamiphos | ||
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fenamiphos | ||
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fenamifos | ||
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fenamifos | ||
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fenamiphos | ||
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fenamifos | ||
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fenamifos |
Record last updated: | 19/01/2021 |
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 |