Prometryn (Ref: C 34161)	Last updated: 24/10/2024
(Also known as: prometryne)

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SUMMARY

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
Environmental fate High alert: Potential for particle bound transport: High	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

Description	A herbicide used to control annual grasses and broadleaved weeds in a variety of crops
Example pests controlled	Grasses including Barnyardgrass, goosegrass, ryegrass, prairies grass; Broadleaved weeds including deadnettle, nightshade, chickweed, fathen, common spurry
Example applications	Cotton; Celery; Pigeon peas; Dill; Potatoes; Sunflowers; Carrots; Peanuts
Efficacy & activity	-
Availability status	Current
Introduction & key dates	1964, first registered USA

GB regulatory status

GB COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
GB LERAP status	No UK approval for use as a plant protection agent

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Not approved
Dossier rapporteur/co-rapporteur	Not applicable
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	Not applicable
Listed in EU database	Yes
Approved for use (✓) under EC 1107/2009 in the following EU Member States	ATAustria BEBelgium BGBulgaria CYCyprus CZCzech Republic DEGermany DKDenmark EEEstonia ELGreece                   ESSpain FIFinland FRFrance HRCroatia HUHungary IEIreland ITItaly LTLithuania LULuxembourg                   LVLatvia MTMalta NLNetherlands PLPoland PTPortugal RORomania SESweden SISlovenia SKSlovakia
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries	ISIceland NONorway

Additional information

Also used in	Australia; USA

Chemical structure

Isomerism	None
Chemical formula	C₁₀H₁₉N₅S
Canonical SMILES	CC(C)NC1=NC(=NC(=N1)SC)NC(C)C
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	AAEVYOVXGOFMJO-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C10H19N5S/c1-6(2)11-8-13-9(12-7(3)4)15-10(14-8)16-5/h6-7H,1-5H3,(H2,11,12,13,14,15)
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
prometryn	-

General status

Pesticide type	Herbicide; Other substance
Other bioactivity & uses	Biocide; Preservative; Slimicide; Antifouling agent
Substance groups	Triazine herbicide; Methylthiotriazine herbicide
Minimum active substance purity	96%
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	A selective, systemic, contact and residual triazine, a photosynthetic electron transport inhibitor at the photosystem II receptor site
CAS RN	7287-19-6
EC number	230-711-3
CIPAC number	93
US EPA chemical code	080805
PubChem CID	4929
Molecular mass	241.36
PIN (Preferred Identification Name)	-
IUPAC name	N2,N4-diisopropyl-6-methylthio-1,3,5-triazine-2,4-diamine
CAS name	N,N'-bis(1-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine
Other status information	Potential groundwater contaminant
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Class (HRAC MoA class)	C1
Herbicide Resistance Class (WSSA MoA class)	5
Insecticide Resistance Class (IRAC MoA class)	Not applicable
Fungicide Resistance Class (FRAC MOA class)	Not applicable
Examples of recorded resistance	-
Physical state	Colourless crystalline solid

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Ciba Geigy Makhteshim-Agan BOC Sciences
Example products using this active	Caparol Gesaguard Primetol Q Prometex
Formulation and application details	Often supplied as a wettable powder

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		33	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)		240000	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data Acetone	-
		5500	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data Hexane	-
		160000	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data Methanol	-
		170000	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data Toluene	-
Melting point (°C)		119	E4 E = Manufacturers safety data sheets 4 = Verified data	-
Boiling point (°C)		300	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	2.19 X 1003	Calculated	-
	Log P	3.34	G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here ) 4 = Verified data	High
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		1.157	E4 E = Manufacturers safety data sheets 4 = Verified data	-
Dissociation constant pKa) at 25 °C		4.1	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source at 25 °C	-
		Weak base, pKb = 9.95
Vapour pressure at 20 °C (mPa)		0.13	G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here ) 4 = Verified data	Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		1.20 X 10-03	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Non-volatile
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
Surface tension (mN m⁻¹)		-	-	-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT₅₀ (typical)	41	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderately persistent
	DT₅₀ (lab at 20 °C)	41	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderately persistent
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Other sources: DT₅₀ 60 days (DW4)
Dissipation rate RL₅₀ (days) on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ (days) on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	30	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Stable
	Note	Degraded by UV light
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	Stable	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Stable
	Note	Stable under normal environmental conditions, hydrolysed in acidic and alkaline media
Water-sediment DT₅₀ (days)		38	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	Moderately fast
Water phase only DT₅₀ (days)		56	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Stable
Sediment phase only DT₅₀ (days)		-	-	-
Air degradation		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.
Decay in stored produce DT₅₀		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here ) 3 = Unverified data of known source	Moderately mobile
	Koc (mL g⁻¹)	400
	Notes and range	-
Freundlich	Kf (mL g⁻¹)	53.26	R4 R = Peer reviewed scientific publications 4 = Verified data	Non-mobile
	Kfoc (mL g⁻¹)	4330
	1/n	0.86
	Notes and range	Kf range 4.22-165 mL g⁻¹, Kfoc range 122-12692 mL g⁻¹, 1/n range 0.57-1.18, Soils=3
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		0.59	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	1.13 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		High	Calculated	-
Potential for loss via drain flow		Moderately mobile	Calculated	-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	85	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 ) 4 = Verified data Whole fish	Low potential
	CT₅₀ (days)	Not available		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
2-methylthio-4-amino-6-isopropylamino-S-triazine (Ref: GS-11354)	-	-	-
2,4-bis(isopropylamino)-6-hydroxy-S-triazine	-	-	Aerobic
2-hydroxy-propazine	-	-	-
hydroxypropazine (Ref: GS-11526)	-	-	-

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 2000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Low
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Rat 2 yr	-
	(ppm diet)	750		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		> 2150	G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here ) 4 = Verified data Anas platyrhynchos	Low
Birds - Short term dietary (LC₅₀/LD₅₀)		> 500 ppm	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source Anas platyrhynchos	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		153	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Soil micro-organisms		-	-	-
Collembola	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Non-target plants		-	-	-
		-	-	-
Honeybees (Apis spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	99	G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here ) 4 = Verified data	Moderate
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Chronic	-	-	-
	Notes	-
Bumblebees (Bombus spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
		-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
		-
Mason bees (Osmia spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
Other bee species (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other bee species (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Beneficial insects (Ladybirds)		-	-	-
Beneficial insects (Lacewings)		Harmless at dose 10 g ha⁻¹	AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005 2 = Unverified data of unknown source Chrysoperla carnea	-
Beneficial insects (Parasitic wasps)		-	-	-
Beneficial insects (Predatory mites)		-	-	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		5.5	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Oncorhynchus mykiss	Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		0.08	P3 P = Other non-EU, UK or US Governments and Regulators 3 = Unverified data of known source Cyprinus carpio 60 day	Moderate
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		2.3	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 ) 4 = Verified data Danio rerio	Moderate
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		12.66	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Daphnia magna	Moderate
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		2	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 ) 3 = Unverified data of known source Daphnia magna	Moderate
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		-	-	-
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)		1.4	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 ) 3 = Unverified data of known source Americamysis bahia	Moderate
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 (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)		0.0105	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 ) 3 = Unverified data of known source Lemna gibba	Moderate
Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		0.002	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 ) 4 = Verified data Scenedesmus acutus	High
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		> 0.0025	P3 P = Other non-EU, UK or US Governments and Regulators 3 = Unverified data of known source Chlamydomonas reinhardtii	Moderate
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-
Marine bivalves		-	-	-

HUMAN HEALTH AND PROTECTION

General

Property		Value	Source; quality score; and other information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 2000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		2020	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rabbit	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		> 5.17	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		-	-	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		-	-	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Routes	Public	-
	Occupational	-
MRLs	European	EU MRL pesticide database
	Great Britain	GB MRL Register
	Notes	-
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-
Mammalian dose elimination route and rate		-	-	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor XNo, known not to cause a problem A3 A = Chromosome aberration (EFSA database) 3 = Negative ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E3 E = Unspecified genotoxicity type (miscellaneous data source) 3 = Negative ✓Yes, known to cause a problem Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant XNo, known not to cause a problem XNo, known not to cause a problem ?Possibly, status not identified Respiratory tract irritant Skin irritant Skin sensitiser ?Possibly, status not identified XNo, known not to cause a problem XNo, known not to cause a problem Eye irritant Phototoxicant   ?Possibly, status not identified No data found
General human health issues		Possible kidney and liver toxicant Possible blood toxicant

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	Health: H332 Environment: H400, H410
WHO Classification	III (Slightly hazardous)
UN Number	UN3077
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	Limited shelf-life

TRANSLATIONS

Language	Name
English	prometryn
French	prometryne
German	Prometryn
Danish	prometryn
Italian	prometrina
Spanish	prometrina
Greek	-
Polish	prometryn
Swedish	-
Hungarian	prometryn
Dutch	-
Norwegian	-

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Record last updated:	24/10/2024
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