Napropamide (Ref: R 7465) |
![]() Last updated: 23/02/2021 |
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(Not known by any other names) |
SUMMARY |
Napropamide is a widely used herbicide approved for use on the EU and many other countries. It has a low mammalian toxicity but is is a known skin and eye irritant. It is moderately soluble in water, and is quite volatile. It is moderately persistent in soil systems and data suggests that under certain conditions it may be persistent in water. It has a low toxicity to birds but is moderately toxic to most aquatic species, honeybees and earthworms. |
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A soil applied herbicide for pre-emergence control of weeds in a range of crops including oilseed rape, fruit and woody ornamentals | |
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Annual grasses; Broad-leaved weeds | |
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Vegetables, Fruit tree and bushes; Vines; Tobacco; Olives; Sunflowers; Turf; Oilseed rape; Ornamentals | |
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Current | |
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circa 1970 |
UK regulatory status |
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Approved | ||
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31/12/2026 | ||
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None |
EC Regulation 1107/2009 (repealing 91/414) |
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Approved | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Solvenia/Hungary | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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31/12/2023 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Yes | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Also used in |
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Australia |
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Chemical structure |
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A ciral molecule. The technical material is a racemate composed of equimolar amounts of (S)- and (R)-napropamide. | |
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C₁₇H₂₁NO₂ | |
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CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21 | |
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No data | |
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WXZVAROIGSFCFJ-UHFFFAOYSA-N | |
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InChI=1S/C17H21NO2/c1-4-18(5-2)17(19)13(3)20-16-12-8-10-14-9-6-7-11-15(14)16/h6-13H,4-5H2,1-3H3 | |
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Yes |
General status |
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Herbicide | |
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Alkanamide | |
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930 g kg⁻¹ | |
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EU dossier - toluene <0.14% | |
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Synthetic | |
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Selective, systemic, absorbed through roots and translocated. Acts by preventing root cell elongation and so disrupting growth. Inhibition of VLCFA (inhibition of cell division). | |
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15299-99-7 | |
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239-333-3 | |
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271 | |
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103001 | |
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27189 | |
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271.36 | |
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- | |
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(RS)-N,N-diethyl-2-(1-naphthyloxy)propionamide | |
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N,N-diethyl-2-(1-naphthalenyloxy)propanamide | |
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Potential groundwater contaminant; PAN listed Highly Hazardous Chemical | |
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- | |
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K3 | |
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15 | |
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Not applicable | |
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Not applicable | |
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Colourless crystals to light brown solid depending on purity |
Formulations |
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Usually supplied as a suspension concentrate, emulsifiable concentrate, wettable powder or ganules |
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74.0 | 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 ) 5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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440000 | 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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11100 | 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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290000 | 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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692000 | 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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74.8 | 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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316.7 | 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 | 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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1.18 | 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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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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2.2 X 10-02 | 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 ) 5 = Verified data used for regulatory purposes |
Low volatility | ||||||||
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8.1 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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Neutral solution 215nm = 58800, 282nm = 10500 Acidic solution 215nm = 58600, 282nm = 10900 |
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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66.0 | 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 ) at 20°C5 = Verified data used for regulatory purposes |
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Degradation |
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70 | G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data |
Moderately persistent | |||||||
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308 | 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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72 | 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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1000 | 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 |
Very persistent | ||||||||
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290 | 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 |
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EU dossier lab studies DT₅₀ range 120-400 days, DT₉₀ >1000 days; field studies DT₅₀ range 31-127 days, DT₉₀ range 180-400 days; Other sources: 8-12 weeks (R3) | ||||||||||
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1.5 | 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 |
Moderately fast | |||||||
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Mid-European conditions | ||||||||||
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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 7, 25 and 40 °C | ||||||||||
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316 | 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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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 ) 5 = Verified data used for regulatory purposes |
Slow |
Soil adsorption and mobility |
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21.5 | 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 |
Slightly mobile | |||||||
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839 | ||||||||||
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EU dossier Kd range 6.87-47.4 mL g⁻¹, Koc range 435-1609 mL g⁻¹, Soils=5 | ||||||||||
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21.6 | 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 |
Slightly mobile | |||||||
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885 | ||||||||||
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0.815 | ||||||||||
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EU dossier Kf range 8.1-44.5 mL g⁻¹, EU dossier Kfoc range 409-1593 mL g⁻¹, 1/n range 0.720-0.815, Soils=5 | ||||||||||
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No |
Fate indices |
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1.96 | Calculated | Transition state | ||||||||||||||||||||||||||
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7.58 X 10-02 | Calculated | - | |||||||||||||||||||||||||
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Medium | Calculated | - | ||||||||||||||||||||||||||
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Slightly mobile | Calculated | - |
Key metabolites |
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Soil | 0.01 | Minor fraction, Not relevant |
Other known metabolites |
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N,N-diethyl-2-(4-hydroxynaphthalen-1-yl)propanamide | hydroxy napropamide isomer 1 | a=Surface water (photolysis); b=Sediment | a=0.20 | - | |||||
N,N-diethyl-2-(1-hydroxynaphthalen-2-yl)propanamide | hydroxy napropamide isomer 2 | a=Surface water (photolysis); b=Sediment | a=0.27 | - | |||||
N-ethylethanamine | diethylamine | a=Surface water (photolysis); b=Sediment | a=0.26 | - | |||||
2-methylnaphtho[1,2-b]furan-3(2H)-one | MNF | a=Surface water (photolysis); b=Sediment | a=0.15 | - | |||||
[4-glucuronyl-(N-ethyl-2-(1-naphthoxy)) propionamide] | 4-OGlu-DE-NPAM | Rat (urine, faeces) | - | - | |||||
N-({4-[(1-amino-1-oxopropan-2-yl)oxy]naphthalen-1-yl}oxy)glutamic acid | 4-OGlu-NOPAM | Rat (urine, faeces) | - | - | |||||
N-{[4-(1-carboxyethoxy)naphthalen-1-yl]oxy}glutamic acid | 4-OGlu-NOPA | Rat (urine, faeces) | - | - | |||||
naphthalene-1,4-dione | NQ | Plant | - | - | |||||
2-hydroxynaphthalene-1,4-dione | HNQ | Plant | - | - | |||||
benzene-1,2-dicarboxylic acid | PA | Plant | - | - | |||||
1-naphthol | 1-naphthol | Plant | - | - | |||||
[4-glucuronyl-(N,N-diethyl-2-(1-naphthoxy)) propionamide] | 4-OGlu-NPAM | Rat (urine, faeces) | - | - | |||||
2,2'-(4,4'-dihydroxy-1,1'-binaphthalene-3,3'-diyl)bis(N,N-diethylpropanamide) | dimer | a=Surface water (photolysis); b=Sediment | a=0.09 | - |
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98 | 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 potential | |||||||
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Not available | - | |||||||||
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> 4680 | 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 |
Low | ||||||||
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30 | L3 L = Pesticide manuals and hard copy reference books / other sources Rat3 = Unverified data of known source |
High | |||||||
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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 ) Rat Reproductive NOAEL5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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> 2250 | 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 |
Low | ||||||||
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> 7200 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 ) Anas platyrhynchos5 = Verified data used for regulatory purposes |
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309 | 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 virginianus NOAEL5 = Verified data used for regulatory purposes |
Low | ||||||||
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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 ) Salmo gairdneri5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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1.1 | 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 ) Salmo gairdneri5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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14.3 | 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 ) Daphnia magna5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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4.3 | 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 ) Daphnia magna5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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3.1 | 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 |
Moderate | ||||||||
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0.24 | 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 ) Lemna gibba5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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310 | 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 ) Avena fatua5 = Verified data used for regulatory purposes Vegetative vigour, ER₅₀ as g ha⁻¹ |
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> 4500 | 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 ) Avena fatua5 = Verified data used for regulatory purposes Seedling emergence, ER₅₀ as g ha⁻¹ |
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3.4 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) Pseudokirchneriella subcapitata4 = Verified data |
Moderate | ||||||||
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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 ) Apis mellifera5 = Verified data used for regulatory purposes |
Low | |||||||
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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 ) Apis mellifera5 = Verified data used for regulatory purposes |
Low | ||||||||
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282.0 | 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 |
Moderate | ||||||||
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30.0 | 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 |
Moderate | ||||||||
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0.0 | Mortality [Dose: 4.5 kg 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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6.0 | Mortality [Dose: 4.5 kg 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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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: 2.25 g ha⁻¹ |
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General |
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High (class III) | - | - | ||||||||
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> 4680 | 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 |
Low | ||||||||
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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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> 4.8 | 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 ) Rat 4 hr5 = Verified data used for regulatory purposes |
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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 ) Rat SF=1005 = Verified data used for regulatory purposes |
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None allocated | 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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0.5 | 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 ) Dog SF=1004 = Verified data |
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0.7-13.4 | 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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Risk to bystanders acceptable for proposed uses | |||||||||
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Risks identified for operators - PPE/PPC advised | ||||||||||
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Health issues |
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Possible liver and kidney toxicant |
Handling issues |
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Not explosive or oxidising IMDG Transport Code is usually 9 |
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Health: H319 Environment: H410, H411 |
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N - Dangerous for the environment: R50, R53 | |||
|
- | |||
|
U (Unlikely to present an acute hazard) | |||
|
Usually 3082 | |||
|
Packaging Group III (minor danger) |
|
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|
||
---|---|---|---|
|
napropamide | ||
|
napropamide | ||
|
Napropamid | ||
|
napropamid | ||
|
napropamide | ||
|
napropamida | ||
|
- | ||
|
napropamid | ||
|
napropamid | ||
|
napropamid | ||
|
- |
Record last updated: | 23/02/2021 |
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 |