Bupirimate (Ref: PP 588) |
Last updated: 17/07/2024 |
(Also known as: bupirimat; R-70588) |
SUMMARY |
A pyrimidine fungicide active against powdery mildew. It has a low aqueous solubility and a low volatility. Depending on local conditions, bupirimate may be moderately persistent in both soil and aquatic systems. It is moderately toxic to most fauna and flora species. It has a low oral toxicity to mammals and is a skin and eye irritant. |
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.
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A pyrimidine fungicide active against powdery mildew | |
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Powdery mildew | |
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Apples; Pumpkins; Squash; Strawberry; Blackcurrant; Raspberry; Gooseberry; Hops; Courgette; Ornamentals | |
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- | |
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Current | |
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1975, first reported; 1975, first marketed |
UK regulatory status |
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Approved | ||
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31/08/2029 | ||
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Crop 5m - See Authorisation for Crop LERAP Details |
EC Regulation 1107/2009 (repealing 91/414) |
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Approved | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Netherlands/Poland | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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31/01/2027 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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No | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Yes | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Additional information |
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Australia, Morocco |
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Chemical structure |
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None | |
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C₁₃H₂₄N₄O₃S | |
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CCCCC1=C(N=C(N=C1OS(=O)(=O)N(C)C)NCC)C | |
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No data | |
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DSKJPMWIHSOYEA-UHFFFAOYSA-N | |
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InChI=1S/C13H24N4O3S/c1-6-8-9-11-10(3)15-13(14-7-2)16-12(11)20-21(18,19)17(4)5/h6-9H2,1-5H3,(H,14,15,16) | |
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Yes |
General status |
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Fungicide | |
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Pyrimidine fungicide | |
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945 g kg⁻¹ | |
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EU dossier - ethirimol, toluene | |
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Synthetic | |
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Systemic with curative and protectant action. Nucleic acid synthesis - adenosin-deaminase. | |
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41483-43-6 | |
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255-391-2 | |
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261 | |
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228100 | |
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38884 | |
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612-288-00-0 | |
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316.42 | |
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5-butyl-2-(ethylamino)-6-methylpyrimidin-4-yl dimethylsulfamate | |
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5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate | |
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5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl dimethylsulfamate | |
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- | |
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- | |
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Not applicable | |
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Not applicable | |
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Not applicable | |
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8 | |
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- | |
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Fine white powder to waxy tan coloured solid depending upon purity |
Formulations |
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Usually supplied as an emulsifiable concentrate that is mixed with water and applied as a spray |
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13.06 | 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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23670 | 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 |
- | ||||||||
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 ) Xylene5 = Verified data used for regulatory purposes |
- | |||||||||
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 ) Methanol5 = Verified data used for regulatory purposes |
- | |||||||||
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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46.9 | 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 |
- | ||||||||
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232 | 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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- | - | - | ||||||||
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- | - | - | ||||||||
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4.79 X 1003 | Calculated | - | |||||||
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3.68 | 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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Soluble | 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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Regulatory data - observed in metabolism and farm animal feeding studies | 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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1.2 | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
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4.4 | 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 ) 5 = Verified data used for regulatory purposes |
- | ||||||||
Weak acid | |||||||||||
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0.057 | 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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1.35 | 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 volatile | ||||||||
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- | - | - | |||||||
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- | - | - | ||||||||
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Neutral solution: 241nm = 21400 Acidic solution: 218nm = 14300, 235nm = 21800 Basic solution: 241nm = 21200 |
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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35.4 | 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 ) at 25°C5 = Verified data used for regulatory purposes |
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Degradation |
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- | ||||||||||
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79 | K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data |
Moderately persistent | |||||||
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107 | 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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34 | 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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332 | 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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- | - | - | ||||||||
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- | - | - | ||||||||
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EU dossier lab studies DT₅₀ range 54.4-734 days, DT₉₀ range 126-1432 days; field studies DT₅₀ range 23-69 days; Defra state DT₅₀ range 35-90 days | ||||||||||
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3.5 | R3 R = Peer reviewed scientific publications 3 = Unverified data of known source |
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Cucumber leaves, undercover, n=1 | ||||||||||
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- | - | - | |||||||
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- | ||||||||||
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0.02 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
Fast | |||||||
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- | ||||||||||
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30 | 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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Not greatly senstive to pH but faster under acid conditions | ||||||||||
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42.5 | 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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6.2 | 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 |
Moderately fast | ||||||||
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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- |
Soil adsorption and mobility |
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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 |
Slightly mobile | |||||||
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1882 | ||||||||||
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0.94 | ||||||||||
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EU dossier Kf range 12-125 mL g⁻¹, Kfoc range 882-2822 mL g⁻¹, 1/n range 0.871-1.017, Soils=5 | ||||||||||
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No |
Fate indices |
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1.11 | Calculated | Low leachability | ||||||||||||||||||||||||||
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2.27 X 10-02 | Calculated | - | |||||||||||||||||||||||||
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- | ||||||||||||||||||||||||||||
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Medium | Calculated | - | ||||||||||||||||||||||||||
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Slightly mobile | Calculated | - | ||||||||||||||||||||||||||
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1.0 | 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 ) Calculated using the Atkinson method, 12 hr4 = Verified data |
Below the level of concern for long-range air transport | ||||||||||||||||||||||||||
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185 | 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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Not available | - |
Known soil metabolites |
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Major fraction | 0.142 | - | |||||
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Minor fraction | - | - | |||||
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Major fraction | 0.412 | - |
Known groundwater metabolites |
None
Other known metabolites |
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4-(2-hydroxy-4-ethylamino-6-methylpyrimidinyl)-butan-2-ol | 3-hydroxy ethirimol | Rat (Urine); Plant | - | ||||
- | ethirimol-glucuronide | Rat (Urine, Bile) | - | ||||
- | methoxy-hydroxy-methyl ethirimol | Surface water | - | ||||
- | de-ethyl-bupirimate; DE-B | Surface water; Sediment | - | ||||
2-amino-5-butyl-6-methylpyrimidin-4-ol | de-ethyl-ethirimol | Plant | - | ||||
1-ethylguanidine | ethyl guanidine | Plant | - | ||||
urea | - | Plant | - | ||||
guanidine | - | Plant | - | ||||
ethirimol (Ref: PP149) | PP149 | Surface water; Sediment; Plant | - |
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Terrestrial ecotoxicology |
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4000 | 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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> 100 | L3 L = Pesticide manuals and hard copy reference books / other sources Rat3 = Unverified data of known source |
Moderate | |||||||
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> 1000 | - | |||||||||
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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 ) Unknown species Reproductive NOAEL5 = Verified data used for regulatory purposes |
Low | ||||||||
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> 10000 | 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 ) Coturnix japonica5 = Verified data used for regulatory purposes |
Low | ||||||||
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> 2091 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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≥ 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 ) Coturnix japonica5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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> 500 | 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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7.3 | 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 ) 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: 0.4 mg kg⁻¹ 28 Day |
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9.0 | 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 ) Formosia candida corr5 = Verified data used for regulatory purposes |
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> 50 | 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 |
Moderate | |||||||
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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 ) Apis mellifera5 = Verified data used for regulatory purposes |
Low | ||||||||
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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 ) Chrysoperla carnea5 = Verified data used for regulatory purposes |
- | ||||||||
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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 ) Aphidius rhopalosiphi Mummies4 = Verified data |
- | ||||||||
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61 | 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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1.0 | 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 ) Lepomis macrochirus5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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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 ) Oncorhynchus mykiss5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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> 3.41 | 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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0.56 | 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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1.6 | 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 ) Pseudokirchneriella subcapitata5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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General |
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High (class III) | - | - | ||||||||
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4000 | 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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> 4.9 | 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 ) Rat5 = Verified data used for regulatory purposes |
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0.05 | 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 ) Dog SF=1005 = Verified data used for regulatory purposes |
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None alocated | 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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0.05 | 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 ) Dog SF=1005 = Verified data used for regulatory purposes |
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1.3-12.0 | 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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Acceptable for proposed uses | |||||||||
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Acceptable for proposed uses - PPE advised | ||||||||||
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Health issues |
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Possible liver & thyroid toxicant Endocrine issues - Activation of Pregnane X cellular receptor CLP data - suspected carcinogen |
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: H317, H351 Environment: H410 |
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III (Slightly hazardous) | |||
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UN3077 | |||
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Packaging Group III (minor danger) | |||
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bupirimate | ||
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bupirimate | ||
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Bupirimat | ||
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bupirimat | ||
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bupirimate | ||
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bupirimato | ||
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bupirymat | ||
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bupirimate | ||
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bupirimaat | ||
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Record last updated: | 17/07/2024 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |