azimsulfuron ** DPX A 8947 ** DPX 47 ** Translations

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SUMMARY

A sulfonylurea herbicide that is approved at EU level for use but is not approved in the UK. It is highly soluble in water, semi-volatile and, based on its physico-chemical properties, appears to have potential for leaching to groundwater. It is not expected to be persistent in the field but can be persistent in water systems. It has a low mammalian toxicity but has high potential for bioaccumulation. No adverse health effects have been identified. Azimsulfuron is modertaely toxic to algae, honeybees and eathworms but less so to birds and fish.

GENERAL INFORMATION
for azimsulfuron

Description: A post-emergence pyrimidinylsulfonylurea herbicide for the control of a range of broad-leaved and sedge weeds in paddy fields and other crops

Example pests controlled: Cyperus spp.; Fimbristylis miliacea; Barnyard grass; Water plantain; Arrowhead; Dirty Dora; Spikerush; Starfruit; Alisma

Example applications: Paddy fields; Aquatic situations

Availability status: Current

Introduction & key dates: 1995

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

Status	Approved
Dossier rapporteur/co-rapporteur	Sweden/Slovenia
Date inclusion expires	31/12/2021

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

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia

General status:

Pesticide type	Herbicide
Substance group	Sulfonylurea
Minimum active substance purity	980 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Selective, absorbed by foliage. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
CAS RN	120162-55-2
EC number	Not assigned
CIPAC number	584
US EPA chemical code	-
Chiral molecule	No
Chemical formula	C13H16N10O5S
SMILES	O=C(Nc1nc(OC)cc(OC)n1)NS(=O)(=O)c2c(cnn2C)c3nn(nn3)C
International Chemical Identifier key (InChIKey)	MAHPNPYYQAIOJN-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C13H16N10O5S/c1-22-11(7(6-14-22)10-18-21-23(2)19-10)29(25,26)20-13(24)17-12-15-8(27-3)5-9(16-12)28-4/h5-6H,1-4H3,(H2,15,16,17,20,24)
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	424.40
PIN (Preferred Identification Name)	N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide
IUPAC name	1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-ylsulfonyl]urea
CAS name	N-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide
Other status information	Australian NOHSC List of Designated Hazardous Substances
Herbicide Resistance Classification (HRAC)	B
Herbicide Resistance Classification (WSSA)	2
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Cyperus difformis Echinochloa colona Lindernia dubia
Physical state	White powdery solid
Related substances & organisms	-

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	DuPont
Example products using this active	Gulliver Azimsulfuron 50WG Segment
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	May be supplied as water-dispersible granules.

ENVIRONMENTAL FATE
for azimsulfuron

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		1050	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		26400	A5 - Acetone	-
		13000	A5 - Ethyl acetate	-
		2100	A5 - Methanol	-
		1800	A5 - Toluene	-
Melting point (oC)		170	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		180	A4	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	F3	-
Octanol-water partition coefficient at pH 7, 20oC	P	3.98 X 10-02	Calculated	-
	Log P	-1.4	A5 - @ 25 degC	Low
Bulk density (g ml-1)/Specific gravity		1.12	A5	-
Dissociation constant (pKa) at 25oC		3.6	A5	-
		Note: Weak acid
Vapour pressure at 25oC (mPa)		4.00 X 10-06	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		5.00 X 10-10	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		6.64 X 10-13	Calculated	Non-volatile
GUS leaching potential index		3.91	Calculated	High leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.04 X 10+00	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		242nm = 23014, 23988, 24099	A5	-
Surface tension (mN m-1)		68.1	A5 at 24 oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	64	A5 Unflooded soil	Moderately persistent
	DT50 (lab at 20oC)	64.2	A5 Unflooded soil	Moderately persistent
	DT50 (field)	3.5	R4	Non-persistent
	DT90 (lab at 20oC)	166	A4 Unflooded soil	-
	DT90 (field)	-	-	-
	Note	EU dossier lab studies DT50 range 17.3-133 days & DT90 range 66.6-529 days for non-flooded situations, DT50 range 12.1-51.0 days & DT90 range 58.7-169 day whole system; Other literature studies give field DT50 2-5 days; Australian registration dossier 18-134 days European soils (A5)
Plant matrix DT50 (days)	Value	3.3	R4	-
	Note	DT50 range 2.4 - 4.2 days, rice, whole plant
Aqueous photolysis DT50 (days) at pH 7	Value	164	A5	Stable
	Note	pH sensitive: 103 days @ pH 5, 225 days @ pH 9, all at 20 deg C
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	124	A5	Persistent
	Note	pH sensitive: 89 days @ pH 5, 124 days @ pH7, 132 days @ pH 9 all at 26 degC
Water-sediment DT50 (days)		112	A5	Slow
Water phase only DT50 (days)		44.5	A5	Stable

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	1.14	A5	Mobile
	Koc	73.8
	Notes and range	EU dossier Kd range 0.69-1.65 mL/g, Koc range 48-94 mL/g, Soils=4
Freundlich	Kf	1.11	A5	Mobile
	Kfoc	68.6
	1/n	0.93
	Notes and range	EU dossier Kf range 0.75-1.31 mL/g, Kfoc range 54-78 mL/g, 1/n range 0.88-0.98, Soils=4
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	91/414 relevancy
1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide (Ref: IN-A8342)		Soil / Flooded soil	0.280 / 0.06	Major fraction, Relevant
1-amino-4,6-dimethoxypyrimidine (Ref: IN-J0290)		Soil / Flooded soil	0.24 / 0.03	Major fraction, Relevant
N-(((aminoiminomethyl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulphonamide (Ref: IN-KQ962)		Soil / Flooded soil	0.13 / 0.075	Major fraction, Relevant
N-((4-hydroxy-6-methoxypyrimidin-2-yl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide (Ref: IN-JJ999)		Soil / Flooded soil	0.02 / 0.13	Minor fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
N-(4,6-dimethoxy-2-pyrimidinyl)-beta-D-glucopyranosylamine	N-glucosyl-J0290; glucosyl-J0290	-	-	-
2-amino-6-methoxy-4-pyrimidinol (Ref: IN-H92350)	-	-	-	-

ECOTOXICOLOGY
for azimsulfuron

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	Low risk	A5 Based on LogP < 3	Low potential
	CT50 (days)	-		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	-	L2 Rat, 2 year	-
	(ppm diet)	> 1000		-
Birds - Acute LD50 (mg kg-1)		> 2250	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 5620 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		154	A5 Oncorhynchus mykiss	Low
Fish - Chronic 21 day NOEC (mg l-1)		6.3	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		378	A5 Daphnia magna	Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		5.4	A5 Daphnia magna	Moderate
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)		0.00062	A5 Lemna gibba	High
Non-target plants		2.64	A5 Onion Seedling emeregnce, ER50 as g product/ha	-
		0.45	A5 Sugarbeet Vegetative vigour, ER50 as g product/ha	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.011	A5 Pseudokirchneriella subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		0.003	A5 Selenastrum capricornutum	Moderate
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 25	A3	Moderate
	Oral acute 48 hour LD50 (μg bee-1)	> 200	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 1000	A5 Eisenia foetida	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		12.5	A4 Eisenia foetida, 56 days	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	>54.3	Mortality A5 Typhlodromus pyri	-
	% Effect	2.1	Beneficial capacity Dose: 0.027 g ha-1) A4 Typhlodromus pyri	-
Other arthropod (2)	LR50 g ha-1	>58.8	Mortality A5 Aphidius rhopalosiphi	-
	% Effect	22.6	Beneficial capacity Dose: 0.029 g ha-1) A4 Aphidius rhopalosiphi	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for azimsulfuron

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 5.94	A5 Rat, 4 hr	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.1	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		Not allocated	A5	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.1	A5 Rat, SF=100	-
Dermal penetration studies (%)		100	A3 default	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Negligible risk to bystanders for proposed uses
	Occupational	Occupational exposure possible during product handling - PPE/PPC advised
European MRLs		Click here for the EU MRL pesticide database
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-	-			-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
-		-		-
General human health issues		Possible pancreas toxicant Possible liver and kidney toxicant

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

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxidising
CLP classification 2013		Environment: H400, H410
EC Risk Classification		N - Dangerous for the environment: R50, R53
EC Safety Classification		S61, R60
WHO Classification		U	-	Unlikely to present an acute hazard
US EPA Classification (formulation)		No consensus across products or no products available	-	-
UN Number		-
Waste disposal & packaging		-

TRANSLATIONS
for azimsulfuron

Language	Name
English	azimsulfuron
French	azimsulfuron
German	Azimsulfuron
Danish	azimsulfuron
Italian	azimsulfuron
Spanish	azimsulfuron
Greek	azimsulfuron
Slovenian	azimsulfuron
Polish	azymsulfuron
Swedish	-
Hungarian	-
Dutch	azimsulfuron

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Record last updated: Thursday 20 April 2017
Contact: aeru@herts.ac.uk