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bupirimate (Ref: PP 588)
** bupirimat ** R-70588 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION
for bupirimate

Description: A pyrimidine fungicide active against powdery mildew

Introduction: 1975, first reported; 1975, first marketed

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Netherlands
Date inclusion expires 31/05/2021

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia

General status:
Pesticide type Fungicide
Substance group Pyrimidinol
Substance origin Synthetic
Mode of action Systemic with curative and protectant action
CAS RN 41483-43-6
EC number 255-391-2
CIPAC number 261
US EPA chemical code -
Chiral molecule No
Chemical formula C13H24N4O3S
SMILES CCCCC1=C(N=C(N=C1OS(=O)(=O)N(C)C)NCC)C
International Chemical Identifier (InChI) InChI=1/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)
Structure diagram/image available? Yes
Molecular mass (g mol-1) 316.42
PIN (Preferred Identification Name) 5-butyl-2-(ethylamino)-6-methylpyrimidin-4-yl dimethylsulfamate
IUPAC name 5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate
CAS name 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl dimethylsulfamate
Other status information -
Herbicide Resistance Classification (HRAC) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) 8
Physical state Fine white powder to waxy tan coloured solid depending upon purity
Related substances & organisms

Formulations:
Property Value
Example manufacturers & suppliers of products using this active
  • Makhteshim
Example products using this active
  • Nimrod 25EC
UK LERAP status None
Formulation and application details Usually supplied as an emulsifiable concentrate that is mixed with water and applied as a spray.


ENVIRONMENTAL FATE

for bupirimate

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 13.06 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 23670 A5 - n-Heptane -
250000 A5 - Xylene -
250000 A5 - Methanol -
250000 A5 - Acetone -
Melting point (oC) 46.9 A5 -
Boiling point (oC) 232 A5 -
Degradation point (oC) - - -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 4.79 X 1003 Calculated -
Log P 3.68 A5 High
Bulk density (g ml-1)/Specific gravity 1.2 L3 -
Dissociation constant (pKa) at 25oC 4.4 A5 -
Note: Weak acid
Vapour pressure at 25oC (mPa) 0.057 A5 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 1.35 A5 Moderately volatile
Henry's law constant at 20oC (dimensionless) 4.00 X 10-07 K3 Moderately volatile
GUS leaching potential index 1.38 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Value 3.95 X 10-02 Calculated -
Note -
Potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 Neutral solution: 241nm = 21400; [Acidic solution: 218nm = 14300, 235nm = 21800; [Basic solution: 241nm = 21200 A5 -
Surface tension (mN m-1) 35.4 A5 at 25oC -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 79 K4 Moderately persistent
DT50 (lab at 20oC) 107 A5 Persistent
DT50 (field) 34 A5 Moderately persistent
DT90 (lab at 20oC) 332 A5 -
DT90 (field) - - -
Note 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
Aqueous photolysis DT50 (days) at pH 7 Value 0.02 A5 Fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 30 A5 Moderately persistent
Note Not greatly senstive to pH but faster under acid conditions
Water-sediment DT50 (days) 42.5 A5 Moderately fast
Water phase only DT50 (days) 6.2 A5 Moderately fast

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 46 A5 Slightly mobile
Kfoc 1882
1/n 0.94
Notes and range EU dossier Kf range 12-125 mL/g, Kfoc range 882-2822 mL/g, 1/n range 0.871-1.017, Soils=5
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
ethirimol Soil   0.412   Major fraction, Relevant
de-ethylated bupirimate Soil   0.142   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
4-(2-hydroxy-4-ethylamino-6-methylpyrimidinyl)-butan-2-ol 3-hydroxy ethirimol Rat (Urinary) - -
- ethirimol-glucuronide Rat (Urinary, Bile) - -
- tri-hydroxylated ethirimol Soil - -
- methoxy-hydroxy-methyl ethirimol Water - -


ECOTOXICOLOGY

for bupirimate

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 185 A5 Threshold for concern
CT50 (days) Not available -
Bioaccumulation potential - Calculated Moderate
Mammals - Acute oral LD50 (mg kg-1) 4000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) > 100 L3 Rat Moderate
(ppm diet) > 1000 -
Birds - Acute LD50 (mg kg-1) > 10000 A5 Coturnix japonica Low
Birds - Short term dietary (LC50/LD50) > 2091 mg kg feed-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 1.0 A5 Lepomis macrochirus Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.3 A5 Oncorhynchus mykiss -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 3.41 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.56 A5 Daphnia magna -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) - - -
Algae - Acute 72 hour EC50, growth (mg l-1) 1.6 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees - Acute 48 hour LD50 (μg bee-1) > 50 A5 Contact Moderate
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 61 Mortality
Dose: 0.174 kg ha-1
A5 Typhlodromus pyri
Moderately harmful
Other arthropod (2) LR50 g ha-1 - - -
% Effect 25.1 Parasitation
Dose: 50g ha-1
A5 Aphidius rhopalosiphi
Harmless
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.4 mg kg-1, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for bupirimate

General:
Property Value Source/Quality Score/Other Information Interpretation
Mammals - Acute oral LD50 (mg kg-1) 4000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 4.9 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.05 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.05 A5 Rat, SF=100 (as ethirimol) -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.05 A5 Dog, SF=100 -
Dermal penetration studies (%) 1.3-12.0 A5 concentration dependant -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Acceptable for proposed uses
Occupational Acceptable for proposed uses - PPE advised
Examples of European MRLs (mg kg-1) Value Strawberries: 1.0; Apples, melons; 0.2
Note A5 EU dossier proposals
For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

General human health issues Skin sensitiser
Possible liver & thyroid toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 -
EC Risk Classification Xn - Harmful: R43
N - Dangerous for the environment: R51, R53
EC Safety Classification S36, S37
WHO Classification III - Slightly hazardous
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number Usually 1993
Waste disposal & packaging Packaging Group III (minor danger)


TRANSLATIONS

for bupirimate

Language Name
English bupirimate
French bupirimate
German Bupirimat
Danish bupirimat
Italian bupirimate
Spanish bupirimato
Greek -
Slovenian bupirimat
Polish bupirymat
Swedish -
Hungarian bupirimate
Dutch bupirimaat

Record last updated: Sunday 29 June 2014
Contact: aeru@herts.ac.uk