Cybutryne	Last updated: 22/01/2023
(Not known by any other names)

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SUMMARY

Cybutyrn is a phytoxic biocide. It has a low aqueous solubility and is non-volatile. It is moderately toxic to fish, aquatic invertebrates and plant. It is highly toxic to algae. No information is available on its impact on human health.

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 Moderate alert: Drainflow: Slightly mobile Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate Warning: Significant data are missing	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description	An effective herbicidal biocide mainly used as an antifouling agent in paints for boats and other water vessels
Example pests controlled	Slimes; Moulds; Mosses; Algae
Example applications	-
Efficacy & activity	-
Availability status	Current
Introduction & key dates	-

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Not applicable
UK LERAP status	No UK approval for use

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	Not applicable
EU Candidate for substitution (CfS)	Not applicable
Listed in EU database	No
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	-

Chemical structure

Isomerism	None
Chemical formula	C₁₁H₁₉N₅S
Canonical SMILES	CC(C)(C)NC1=NC(=NC(=N1)NC2CC2)SC
Isomeric SMILES	-
International Chemical Identifier key (InChIKey)	HDHLIWCXDDZUFH-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C11H19N5S/c1-11(2,3)16-9-13-8(12-7-5-6-7)14-10(15-9)17-4/h7H,5-6H2,1-4H3,(H2,12,13,14,15,16)
2D structure diagram/image available?	Yes

General status

Pesticide type	Algistat, Herbicide, Other substance
Other constituent type	Biocide, Antifoulant
Substance groups	Triazine biocide; Triazine herbicide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Reduces plant photosynthetic ability; Highly phytotoxic
CAS RN	28159-98-0
EC number	248-872-3
CIPAC number	None allocated
US EPA chemical code	128996
PubChem CID	91590
CLP index number	No data found
Molecular mass	253.37
PIN (Preferred Identification Name)	N2-tert-butyl-N4-cyclopropyl-6-(methylsulfanyl)-1,3,5-triazine-2,4-diamine
IUPAC name	N2-tert-butyl-N4-cyclopropyl-6-methylthio-1,3,5-triazine-2,4-diamine
CAS name	N-cyclopropyl-N-(1,1-dimethylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine
Other status information	Marine pollutant
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	Not known
Herbicide Resistance Classification (WSSA)	Not known
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	-
Physical state	White crystalline powder

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Zhejiang Zhongshan Ciba Speciality Chemicals
Example products using this active	Irgarol Irgaguard
Formulation and application details	-

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		7.0	R4 R = Peer reviewed scientific publications 4 = Verified data	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		-	-	-
Melting point (°C)		128	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	8.91 X 1003	Calculated	-
	Log P	3.95	R4 R = Peer reviewed scientific publications 4 = Verified data	High
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		-	-	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		0.088	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
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)	-	-	-
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	-
Dissipation rate RL₅₀ on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	14	R4 R = Peer reviewed scientific publications 4 = Verified data	Slow
	Note	Around 2 weeks in natural waters
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	Stable	R4 R = Peer reviewed scientific publications 4 = Verified data	Stable
	Note	Stable at all relevant pH values
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		-	-	-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	R4 R = Peer reviewed scientific publications 4 = Verified data	Slightly mobile
	Koc	1569
	Notes and range	Koc literature values range 548 to 2590 g l⁻¹
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		-	-	-
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	Cannot be calculated	-	-
	Note	-
Potential for particle bound transport index		-	-	-
Potential for loss via drain flow		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	160	R4 R = Peer reviewed scientific publications 4 = Verified data	Threshold for concern
	CT₅₀ (days)	nd		-

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		-	-	-
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	-	-
	(ppm diet)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		-	-	-
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		-	-	-
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)	-	-	-
	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	-	-	-
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)		-	-	-
Beneficial insects (Parasitic wasps)		-	-	-
Beneficial insects (Predatory mites)		-	-	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		0.86	R4 R = Peer reviewed scientific publications 4 = Verified data Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		2.40	R4 R = Peer reviewed scientific publications 4 = Verified data Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
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)		0.011	R4 R = Peer reviewed scientific publications 4 = Verified data Lemna gibba	Moderate
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		0.0023	R4 R = Peer reviewed scientific publications 4 = Verified data Selenastrum capricornutum	High
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-

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)		-	-	-
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		-	-	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		-	-	-
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)		0.1	R4 R = Peer reviewed scientific publications 4 = Verified data	-
Mammalian dose elimination route and rate		-	-	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor No data found A0 A = Chromosome aberration (EFSA database) 0 = No data ; 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 ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data ?Possibly, status not identified Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ✓Yes, known to cause a problem XNo, known not to cause a problem No data found Respiratory tract irritant Skin irritant Skin sensitiser No data found No data found No data found Eye irritant Phototoxicant   No data found No data found
General human health issues		Possible liver and spleen toxicant

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	-
WHO Classification	-
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	cybutryne
French	cybutryne
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	22/01/2023
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