Napropamide (Ref: R 7465) |
Last updated: 31/10/2024 |
(Not known by any other names) |
SUMMARY |
Napropamide is a widely used herbicide. 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. |
Data alerts |
The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.
Environmental fate | Ecotoxicity | Human health |
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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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- | |
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Current | |
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circa 1970, introduced |
UK regulatory status |
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Approved | ||
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31/12/2031 | ||
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Check label - may vary with formulation |
EC Regulation 1107/2009 (repealing 91/414) |
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Approved | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Solvenia/Hungary | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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31/03/2027 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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No | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Yes | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Additional information |
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Australia |
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Chemical structure |
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A chiral 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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Amide herbicide | |
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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 very long chain fatty acids (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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No data found | |
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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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- | |
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Colourless crystals to light brown solid depending on purity | |
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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 |
- | ||||||||
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 |
- | |||||||||
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 |
- | |||||||||
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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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. Available online but no longer updated. (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 | ||||||||
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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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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 | - | ||||||||||||||||||||||||||
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0.552 | 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 ) Calculated using the Atkinson method4 = Verified data |
Below the level of concern for long-range air transport | ||||||||||||||||||||||||||
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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 | - |
Known soil metabolites |
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Minor fraction | 0.01 | - |
Known groundwater metabolites |
None
Other known metabolites |
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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 | ||||
2-methylnaphtho[1,2-b]furan-3(2H)-one | MNF | a=Surface water (photolysis); b=Sediment | a=0.15 | ||||
N,N-diethyl-2-(4-hydroxynaphthalen-1-yl)propanamide | hydroxy napropamide isomer 1 | a=Surface water (photolysis); b=Sediment | a=0.20 | ||||
N-ethylethanamine | diethylamine | a=Surface water (photolysis); b=Sediment | a=0.26 | ||||
N,N-diethyl-2-(1-hydroxynaphthalen-2-yl)propanamide | hydroxy napropamide isomer 2 | a=Surface water (photolysis); b=Sediment | a=0.27 | ||||
[4-glucuronyl-(N,N-diethyl-2-(1-naphthoxy)) propionamide] | 4-OGlu-NPAM | 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 | - | ||||
N-({4-[(1-amino-1-oxopropan-2-yl)oxy]naphthalen-1-yl}oxy)glutamic acid | 4-OGlu-NOPAM | Rat (Urine, Faeces) | - | ||||
[4-glucuronyl-(N-ethyl-2-(1-naphthoxy)) propionamide] | 4-OGlu-DE-NPAM | Rat (Urine, Faeces) | - |
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Terrestrial ecotoxicology |
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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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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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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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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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> 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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6.0 | 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 ) Aphidius rhopalosiphi4 = Verified data |
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0 | 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 ) Typhlodromus pyri4 = Verified data |
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Aquatic ecotoxicology |
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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 / FAO data, IPCS INCHEM data (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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3.4 | F4 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 ) Pseudokirchneriella subcapitata4 = Verified data |
Moderate | ||||||||
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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 Hazard Class 9 Not expected to auto-ignite; Not highly flammable |
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Health: H319 Environment: H410, H411 |
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U (Unlikely to present an acute hazard) | |||
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UN3077 | |||
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Packaging Group III (minor danger) | |||
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Stable and non-reactive under normal conditions of use, storage and transport |
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napropamide | ||
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napropamide | ||
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Napropamid | ||
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napropamid | ||
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napropamide | ||
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napropamida | ||
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napropamid | ||
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napropamid | ||
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napropamid | ||
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Record last updated: | 31/10/2024 |
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 |