Page last updated: 2024-12-07

irgarol 1051

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Irgarol 1051 is a widely used algaecide, primarily in antifouling paints for marine vessels. It is a triazine derivative with the chemical name 2-(tert-butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine. The synthesis involves a multi-step process starting from cyanuric chloride. Irgarol 1051 is highly effective in controlling the growth of algae, which can accumulate on ship hulls and increase drag, leading to reduced fuel efficiency. However, concerns regarding its environmental impact, including potential toxicity to non-target organisms, have led to ongoing research into its effects on marine ecosystems. Its mode of action involves inhibiting photosynthesis in algae, specifically by interfering with the electron transport chain. Studies on Irgarol 1051 focus on understanding its fate and transport in the environment, its effects on marine organisms, and the development of alternative antifouling agents with reduced environmental risks.'

irgarol 1051: a booster biocide; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

irgarol 1051 : A diamino-1,3,5-triazine that is 1,3,5-triazine-2,4-diamine carrying a N-tert-butyl, N'-cyclopropyl and a methylsulfanyl group at position 6. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID91590
CHEMBL ID3185551
CHEBI ID5962
SCHEMBL ID241791
SCHEMBL ID8008580
MeSH IDM0270254

Synonyms (49)

Synonym
irgarol
c11h19n5s
n-tert-butyl-n'-cyclopropyl-6-(methylsulfanyl)-1,3,5-triazine-2,4-diamine
CHEBI:5962 ,
28159-98-0
irgarol 1051
cybutryne
cybutryne [iso]
n'-tert-butyl-n-cyclopropyl-6-(methylthio)-1,3,5-triazine-2,4-diamine
einecs 248-872-3
2-n-tert-butyl-4-n-cyclopropyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine
NCGC00255369-01
dtxsid3032416 ,
tox21_302267
dtxcid1012416
cas-28159-98-0
2-(tert-butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine
I0842
hsdb 8441
1,3,5-triazine-2,4-diamine, n-cyclopropyl-n'-(1,1-dimethylethyl)-6-(methylthio)-
2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine
e7b77o21gh ,
unii-e7b77o21gh
FT-0670416
2-(tert-butylamino)-4-(cyclopropylamino)-6-(methylthio)-s-triazine
irgarol [mi]
n-cyclopropyl-n'-(1,1-dimethylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine
n(sup 2)-tert-butyl-n(sup 4)-cyclopropyl-6-methylthio-1,3,5-triazine-2,4-diamine
SCHEMBL241791
AKOS025310885
SCHEMBL8008580
mfcd01863779
n-tert-butyl-n-cyclopropyl-6-(methylthio)-1,3,5-triazine-2,4-diamine
2-methylthio-4-t-butylamino-6-cyclopropylamino-s-triazine
CHEMBL3185551
HDHLIWCXDDZUFH-UHFFFAOYSA-N
irgarol(r), pestanal(r), analytical standard
irgarol 1051 10 microg/ml in cyclohexane
n2-tert-butyl-n4-cyclopropyl-6-(methylthio)-1,3,5-triazine-2,4-diamine
n2-(tert-butyl)-n4-cyclopropyl-6-(methylthio)-1,3,5-triazine-2,4-diamine
BS-16875
1,3,5-triazine-2,4-diamine, n2-cyclopropyl-n4-(1,1-dimethylethyl)-6-(methylthio)-
Q1147281
2-(tert-butylamino)-4-(cyclopropylamino)-6-(methylthio)-135-triazine
SB73237
D91205
irgarol 1051 100 microg/ml in cyclohexane
CS-W012602
?irgarol

Research Excerpts

Overview

Irgarol 1051 is a common antifouling biocide and is highly toxic to non-target plant species at low ng/L concentrations. It is an algaecide used in copper-based antifoulant paints for controlling fouling organisms on the hulls of recreational and commercial watercraft.

ExcerptReferenceRelevance
"Irgarol 1051 is a common antifouling biocide and is highly toxic to non-target plant species at low ng/L concentrations. "( Antifouling biocides in water and sediments from California marinas.
Fulton, M; Sapozhnikova, Y; Schiff, K; Wirth, E, 2013
)
1.83
"Irgarol 1051 is a photosystem (PS) II inhibitor used in antifouling paint."( A phylogenetic approach to detect selection on the target site of the antifouling compound irgarol in tolerant periphyton communities.
Antonelli, A; Blanck, H; Clarke, AK; Eriksson, KM; Nilsson, RH, 2009
)
1.07
"Irgarol 1051 is a s-triazine herbicide used in popular slime-resistant antifouling paints. "( Contamination of Caribbean coastal waters by the antifouling herbicide Irgarol 1051.
Carbery, K; Frickers, T; Otero, E; Owen, R; Readman, J, 2006
)
2.01
"Irgarol 1051 is an s-triazine herbicide formulated with Cu2O in antifouling paints. "( Preliminary examination of short-term cellular toxicological responses of the coral Madracis mirabilis to acute Irgarol 1051 exposure.
Downs, A; Downs, C, 2007
)
1.99
"Irgarol 1051 is an algistatic compound used in copper-based antifoulant paints. "( Lethal and sublethal toxicity of the antifoulant compound Irgarol 1051 to the mud snail Ilyanassa obsoleta.
DeLorenzo, ME; Finnegan, MC; Pittman, S, 2009
)
2.04
"Irgarol 1051 is an algaecide used in copper-based antifoulant paints for controlling fouling organisms on the hulls of recreational and commercial watercraft. "( An ecological risk assessment for the use of Irgarol 1051 as an algaecide for antifoulant paints.
Balcomb, R; Giddings, JM; Hall, LW; Solomon, KR, 1999
)
2.01
"Irgarol 1051 is a recent herbicidal compound, inhibitor of photosynthesis, used in antifouling paints. "( Toxic effects of Irgarol 1051 on phytoplankton and macrophytes in Lake Geneva.
Becker-Van Slooten, K; Bérard, A; Druart, JC; Grandjean, D; Leboulanger, C; Nyström, B, 2002
)
2.1

Effects

Irgarol 1051 and Diuron have been shown to occur together in concentrations above 0.5 microg/l. This suggests that seagrasses may be experiencing reduced photosynthetic efficie. Irgarol has been found to be present in two of the geographical locations analyzed.

ExcerptReferenceRelevance
"Irgarol 1051 has been widely used as a booster biocide in combination with copper (Cu) in antifouling paints. "( Acute and chronic toxicities of Irgarol alone and in combination with copper to the marine copepod Tigriopus japonicus.
Bao, VW; Lam, MH; Leung, KM; Lui, GC, 2013
)
1.83
"Irgarol 1051 and Diuron have been shown to occur together in concentrations above 0.5 microg/l, suggesting that seagrasses may be experiencing reduced photosynthetic efficie"( The interactive effects of the antifouling herbicides Irgarol 1051 and Diuron on the seagrass Zostera marina (L.).
Brown, MT; Chesworth, JC; Donkin, ME, 2004
)
1.29
"Irgarol 1051 has been found to be present in two of the geographical locations analyzed at concentration levels dependent on the time of year."( Influence of the hapten design on the development of a competitive ELISA for the determination of the antifouling agent Irgarol 1051 at trace levels.
Ballesteros, B; Barceló, D; Camps, F; Marco, MP; Sanchez-Baeza, F, 1998
)
1.23

Toxicity

Irgarol 1051 was not toxic at concentrations below 40x10(3)nM. The EC10 and EC50 for chlorothalonil ranged from 2 to 108 and from 25 to 159 nM. For Sea-Nine 211 values were 6-204 and 38-372 nM; for dichlofluanid effective concentrations were 95-830 and 244-4311 nm.

ExcerptReferenceRelevance
" These results indicate that in this system TBT is acutely more toxic than IRGAROL; however, both are proven environmentally toxic substances."( Acute toxicity of TBT and IRGAROL in Artemia salina.
Iliopoulou-Georgudaki, J; Panagoula, B; Panayiota, M,
)
0.13
" This toxic is persistent in aquatic environments, with low abiotic and biotic degradation, highly phytotoxic, and has already been detected in estuaries and coastal areas, with suspected negative impacts on non-target organisms (aquatic plants and algae)."( Toxic effects of Irgarol 1051 on phytoplankton and macrophytes in Lake Geneva.
Becker-Van Slooten, K; Bérard, A; Druart, JC; Grandjean, D; Leboulanger, C; Nyström, B, 2002
)
0.65
" The tested antifoulants were highly toxic in both tests."( Effects of three antifouling agents on algal communities and algal reproduction: mixture toxicity studies with TBT, Irgarol, and Sea-Nine.
Arrhenius, A; Backhaus, T; Blanck, H; Grönvall, F; Junghans, M; Scholze, M, 2006
)
0.33
" These data show the different sensitivities of the two tests: embryos are more sensitive than sperms for both the tested chemicals and Diuron seems to be the less toxic one."( Toxic effects of irgarol and diuron on sea urchin Paracentrotus lividus early development, fertilization, and offspring quality.
Buono, S; Cremisini, C; Manzo, S, 2006
)
0.33
" The EC10 and EC50 for chlorothalonil ranged from 2 to 108 and from 25 to 159 nM; for Sea-Nine 211 values were 6-204 and 38-372 nM; for dichlofluanid effective concentrations were 95-830 and 244-4311 nM; tolylfluanid yielded values between 99-631 and 213-2839 nM; and Irgarol 1051 was the least toxic compound showing values from 3145 to >25600 and from 6076 to >25600 nM."( Comparative toxicity of alternative antifouling biocides on embryos and larvae of marine invertebrates.
Bellas, J, 2006
)
0.51
" Irgarol 1051 was not toxic at concentrations below 40x10(3)nM."( Comparative toxicity of single and combined mixtures of selected pollutants among larval stages of the native freshwater mussels (Unio elongatulus) and the invasive zebra mussel (Dreissena polymorpha).
Barata, C; Faria, M; Fernández-Sanjuan, M; Lacorte, S; López, MA, 2010
)
1.27
" Generally, Cu(I) appeared to be more toxic than Irgarol 1051: it significantly (p<0."( Immunotoxicity in ascidians: antifouling compounds alternative to organotins: III--the case of copper(I) and Irgarol 1051.
Ballarin, L; Cima, F, 2012
)
0.85
" tauri gives it huge potential for screening many other toxic compounds."( A new, sensitive marine microalgal recombinant biosensor using luminescence monitoring for toxicity testing of antifouling biocides.
Bouget, FY; Joux, F; Leroy, F; Sanchez-Ferandin, S, 2013
)
0.39
" Although data regarding the toxicity of commercial alternative biocides in marine organisms are accumulating, little is known about their toxic pathways or mechanisms."( Overlapping and unique toxic effects of three alternative antifouling biocides (Diuron, Irgarol 1051
Hong, CP; Jung, JH; Kang, JH; Kim, M; Moon, YS, 2019
)
0.74

Compound-Compound Interactions

ExcerptReferenceRelevance
"Irgarol 1051 has been widely used as a booster biocide in combination with copper (Cu) in antifouling paints."( Acute and chronic toxicities of Irgarol alone and in combination with copper to the marine copepod Tigriopus japonicus.
Bao, VW; Lam, MH; Leung, KM; Lui, GC, 2013
)
1.83

Dosage Studied

ExcerptRelevanceReference
" The study simulated a best-case scenario since the mesocosms were dosed only once."( Long-term effects of the antifouling booster biocide Irgarol 1051 on periphyton, plankton and ecosystem function in freshwater pond mesocosms.
Arp, W; Berghahn, R; Feibicke, M; Mohr, S; Nicklisch, A; Schröder, H, 2008
)
0.6
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antifouling biocideA compound that inhibits the growth of marine organisms.
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
aryl sulfideAny organic sulfide in which the sulfur is attached to at least one aromatic group.
cyclopropanesCyclopropane and its derivatives formed by substitution.
diamino-1,3,5-triazineAny member of the class of 1,3,5-triazines that consists of a 1,3,5-triazine skeleton substituted by two amino groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (18)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency3.17060.002541.796015,848.9004AID1347395
RAR-related orphan receptor gammaMus musculus (house mouse)Potency32.45330.006038.004119,952.5996AID1159523
GLI family zinc finger 3Homo sapiens (human)Potency2.62370.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency54.71190.000221.22318,912.5098AID1259243; AID1259247; AID743035; AID743063
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency48.55770.000657.913322,387.1992AID1259378
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency8.03470.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency61.13060.000417.946075.1148AID1346795
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency2.18720.000214.376460.0339AID720692
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency54.48270.003041.611522,387.1992AID1159552; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency36.77180.001530.607315,848.9004AID1224848; AID1224849; AID1259401; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency21.68990.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency48.78210.000229.305416,493.5996AID1259244; AID1259248; AID743075; AID743079
aryl hydrocarbon receptorHomo sapiens (human)Potency1.10420.000723.06741,258.9301AID743085; AID743122
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency62.32630.000323.4451159.6830AID743065; AID743067
heat shock protein beta-1Homo sapiens (human)Potency43.09300.042027.378961.6448AID743210; AID743228
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency58.57370.000627.21521,122.0200AID743202; AID743219
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency68.58960.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency68.58960.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (162)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (3.09)18.2507
2000's85 (52.47)29.6817
2010's67 (41.36)24.3611
2020's5 (3.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.13

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.13 (24.57)
Research Supply Index5.11 (2.92)
Research Growth Index5.57 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (1.21%)6.00%
Case Studies1 (0.61%)4.05%
Observational0 (0.00%)0.25%
Other162 (98.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]