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

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

GENERAL INFORMATION

Description: A pyrimidine fungicide active against powdery mildew

Introduction: 1975, first reported; 1975, first marketed

EC Directive 1107/2009 (repealing 91/414):

Status	Annex 1
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	-
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
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	ethirimol

Formulations:

Property	Value
Example manufacturers 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

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 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	3.43 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

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	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	Harmless	HarmlessAA2 Typhlodromus pyri	Harmless
	% 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 effect Carbon mineralisation: No significant effect	A5 Dose: 0.4 mg/kg, 28 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

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	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
	-					-
General human health issues		[Skin sensitiser], [Possible liver & thyroid sensitiser]

: 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]
EC Risk Classification		[Xi - Irritant: 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		[Usually Packaging Group III (minor danger)]

TRANSLATIONS