Irgarol

253.37

253.37

248-872-3

E7B77O21GH

DTXSID3032416

Crystals from water

2933699090

88

3.9

White Powder

1.3±0.1 g/cm3

128-1330C

428°C at 760 mmHg

163.8±23.2 °C

1.659

In water, 7 mg/L|In water, 9.0 ppm in 0.3 mol/L salinity; 1.8 ppm in 0.6 mol/L salinity

Keep container tightly closed in a dry and well-ventilated place.

1.57E-07mmHg at 25°C

LC50 (96 hr in salt water) in mysid shrimp, inland silverside, sheepshead minnow (ng/l): 400000, 1580000, 3500000; LC50 (96 hr in fresh water) in rainbow trout, bluegill sunfish (ng/l): 790000, 2600000 (Hall)

Henry's Law constant: 3.1X10-8 atm-cu m/mole at 25 °C (est)

MW: 253.4|Hydroxyl radical reaction rate constant = 2.4X10-12 cu cm/molec-sec 25 °C (est)

Ⅲ

9

UN 3077

2

43-50/53

36/37-60-61

XY5850675

Xi;N,N,Xi

Stable under recommended storage conditions.

P273-P280

H317-H400

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 224 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|Not Classified

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Irgarol 1051 was detected in 7 of 24 sewage sludge samples collected Jan and May 2001 from 12 waste water treatment plants in Switzerland at 1.5-30.4 ug/kg dry weight(1). The concentration of Irgarol 1051 in leachates from short-term immersion, permanent immersion and irrigation test was 0.4-1.0, 1.2-3.4 and 0.5-1.7 mg/L, respectively(2). Influent and effluent concentrations of Irgarol 1051 from four German wastewater treatment plants collected Jun 2012 were 2.3-16 and 2.9-14 ng/L, respectively(3).

SEDIMENT: Irgarol 1051 was detected at <10-132 in sediment samples collected Sep 1993 from estuary and rivers of the Southern England coast(1). Irgarol 1051 concentrations decreased from 8 to <0.2 ng/g in sediment collected Aug 1994 to Apr 1995 from Port d'Ouchy, Lake Geneva, Switzerland(2). In sediment samples collected Apr-Nov 1996 from 3 sites in the Stockholm Archipelago, Irgarol 1051 was detected at only one site at <5-9 ng/g dry weight(3). In sediment samples collected Jul-Sep 1997 from marinas of the North and Baltic Sea, Irgarol 1051 was reported at <1.0-220 ng/g dry weight(4). Irgarol 1051 was detected at 0.01-0.11 ug/g dry weight in 6 of 27 sediment samples collected in 1998 from coastal locations of the UK(5). Irgarol 1051 was detected at <3.1-222.3 ppb in 15 sediment samples collected Oct 1998 and Jun 1999 from Blackwater Estuary, Essex, UK(6). Sediment samples collected Oct 1999 to Sep 2000 from Greek ports and marinas contained Irgarol 1051 at 3-690 ng/g dry weight in approximately 10% of the samples(7). Irgarol 1051 was detected at 0.03-3.2 ug/kg dry weight in sediment samples collected Apr 19-20, 2004 from thirteen sites along the coast of Thailand(8). Irgarol 1051 was detected at <0.04-8.2 ug/kg dry weight in samples collected in 2002 and 2003 from 8 sites in the port of Osaka, Japan(9). Sediment samples collected Jul 2004 and Sep 2005 from rivers adjacent to coral reefs in Okinawa, Japan contained Irgarol 1051 at <0.016-0.12 and <0.016-0.051 ug/kg, respectively(10). Irgarol 1051 was detected at <0.1-0.2 ug/kg dry weight in sediment core samples collected Aug 2006 to Aug 2007 from Suruga Bay, Tosa Bay and Nankai Tough, Japan(11). In 6 of 13 sediment samples collected July 2007 from Maizuru Bay, Japan, Irgarol 1051 was detected at 6.8-9.8 ug/g dry weight(12). The maximum reported concentration of Irgarol 1051 in sediment samples collected from southern California recreational marinas was 9 ng/g dry weight(13).

IDENTIFICATION AND USE: Cybutryne is used as a booster algicide in antifouling paint. HUMAN STUDIES: Cybutryne induces HepG2 cell apoptosis through mitochondrial dysfunction and oxidative stress. ANIMAL STUDIES: Cybutryne inhibits the ATP synthesis. The analysis of the various steps involved in the ATP synthesis suggests that the inhibition is due to the opening of small-size pores. ECOTOXICITY STUDIES: When tested on early developmental stages of marine invertebrates cybutryne was found to be the least toxic among other commonly used 'booster'' biocides. However, it was more toxic when tested on the growth of autotrophic species. The toxicity of cybutryne towards periphyton and phytoplankton was shown to be higher than that of atrazine. It induced spermiotoxicity and embryotoxicity at environmentally relevant concentrations in Pacific oyster (Crassostrea gigas) gametes or embryos. It had a significant impact on meiofauna abundance, even at the lowest concentrations, causing a drastic decline in the abundance of nematodes (the dominant meiofaunal taxon) and an increase of the relative importance of oligochaetes. Other study evaluated the effects of cybutryne toxicity on the exoskeleton of Metanephrops japonicus, which is the outer layer facing the environment. Ecdysteroid receptor (Mj-EcR), trypsin (Mj-Tryp), and serine proteinase (Mj-SP) in the hepatopancreas were upregulated in response to different exposure levels of the biocide at day 1, 4, or 7. In contrast, gill Mj-chi5, Mj-Tryp, and Mj-SP exhibited late upregulated responses to 10 ug/L compared to the control at day 7. Mj-chi1 showed early upregulation upon exposure to 10 ug/L and Mj-chi4 showed no changes in transcription in the gill. Gill Mj-EcR presented generally downregulated expression patterns. In addition, decreased survival and change of exoskeleton surface roughness were observed in M. japonicus exposed to the three concentrations of the biocide. Separate studies have shown that cybutryne inhibits coral photosynthesis at environmentally relevant concentrations, consistent with its mode of action as a photosystem II inhibitor.

Three of the most commonly used antifouling booster biocides that are usually combined with copper or copper compounds are Irgarol 1051, Diuron, and Zn pyrithione. This study represents an assessment of the interactive effects of the antifouling biocides combined with each other, and with three heavy metals (Cu, Cd, and Zn) in binary mixtures, on the marine algae Chaetoceros gracilis. Seventy-two hour growth inhibition tests were carried out, and the IC50 values of the chemicals were determined along with growth inhibition (%) for several concentrations. The joint effect of the binary mixtures of all the chemicals was assessed by using two models, concentration addition model and the model of probabilities. The following increasing order of toxicity was obtained: Cd < Zn < Cu < Diuron < Zn pyrithione < Irgarol 1051. The interactive effects of the organic chemicals combined with each other on the growth of Ch. gracilis were firmly synergistic. Irgarol 1051 combined with Cd performed synergistic effects, and Zn pyrithione with copper and cadmium action was strictly antagonistic, and the results of the two models were in agreement in almost all mixtures.|Single and joint effects of two antifouling booster biocides, Irgarol 1051 (2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine) and diuron (1-(3,4 dichlorophenyl)-3,3 dimethyl urea), their metabolites, M1 (2-methylthio-4-tert-butylamino-s-triazine), DCPMU (1-(3,4-dichlorophenyl)-3 methyl urea), DCPU (1-(3,4 dichlorophenyl urea) and DCA (3,4-dichloroaniline), respectively, as well as copper were examined. Two phytoplanktonic microorganisms, the green alga Dunaliella tertiolecta and the diatom Navicula forcipata were exposed to various concentrations of the aforementioned compounds both alone and in binary mixtures during a period of 96 hr. Estimation of EC(50) values was performed by daily cell number counting of the tested microorganisms. The toxicity of the six compounds and the metal, applied singly, was found to be, in decreasing order, Irgarol 1051>diuron>M1>DCPMU>DCA>Cu>DCPU and Irgarol 1051>diuron>M1>DCA for the green alga and the diatom, respectively. Diatoms were found to be more sensitive in the presence of all the tested compounds, except diuron. Co-existence of irgarol 1051 and M1 revealed additive effects on both microorganisms. Same results were observed owing to the joint action of copper with either Irgarol 1051 or M1 for almost all the examined mixtures. Combined effects of diuron with its metabolites DCPMU and DCA resulted in synergism in almost all cases, for both species of phytoplankton. On the contrary, antagonistic effects were observed owing to the joint action of copper with either diuron or one of its metabolites.|Tides and freshwater inflow which influence water movement in estuarine areas govern the exposure-regime of pollutants. In this experiment, we examined the in situ impact of double pulses of copper and the herbicide Irgarol 1051 on the photosynthesis of the seagrass, Zostera capricorni. Despite a 4-day recovery period between the two 10 hr pulses of toxicant, the effective quantum yield of photosystem II (DeltaF/Fm') and total chlorophyll concentrations indicated that multiple-pulses had a greater impact than a single pulse. During the first exposure period, samples exposed to Irgarol 1051 had DeltaF/Fm' values as low as zero while controls remained around 0.6 relative units. After the second exposure period, treated samples recovered to only 0.4 relative units. Samples exposed to copper had DeltaF/Fm' values around 0.3 relative units during the first exposure period and while these samples recovered before the second dose, they remained below 0.2 relative units after the second exposure period. Alternate samples were also exposed to one toxicant, allowed to recover and then exposed to the other toxicant. DeltaF/Fm' values indicated that copper exposure followed by Irgarol 1051 exposure was more toxic than Irgarol 1051 exposure followed by copper exposure.|The herbicides Irgarol 1051 (2-(tert-butylamino)-4-cyclopropylamino)-6-(methylthio)-1,3,5-triazine) and Diuron (3-(3',4'-dichlorophenyl)-1,1-dimethylurea) are commonly incorporated into antifouling paints to boost the efficacy of the compound towards algae. Previous investigations have identified environmental concentrations of these herbicides as being a threat to non-target organisms, such as seagrasses. Their individual toxicity has been assessed, but they can co-occur and interact, potentially increasing their toxicity and the threat posed to seagrass meadows. Chlorophyll fluorescence (Fv:Fm) and leaf specific biomass ratio (representing plant growth) were examined in Zostera marina L. after a 10-day exposure to the individual herbicides. The EC20 for each herbicide was determined and these then used in herbicide mixtures to assess their interactive effects. Irgarol 1051 was found to be more toxic than Diuron with lowest observable effect concentrations for Fv:Fm reduction of 0.5 and 1.0 +/- ug/L and 10-day EC50 values of 1.1 and 3.2 ug/L, respectively. Plants exposed to Irgarol 1051 and Diuron showed a significant reduction in growth at concentrations of 1.0 and 5.0 ug/L, respectively. When Z. marina was exposed to mixtures, the herbicides commonly interacted additively or antagonistically, and no significant further reduction in photosynthetic efficiency was found at any concentration when compared to plants exposed to the individual herbicides. However, on addition of the Diuron EC20 to varying Irgarol 1051 concentrations and the Irgarol 1051 EC20 to varying Diuron concentrations, significant reductions in Fv:Fm were noted at an earlier stage. The growth of plants exposed to Diuron plus the Irgarol 1051 EC20 were significantly reduced when compared to plants exposed to Diuron alone, but only at the lower concentrations. Growth of plants exposed to Irgarol 1051 and the Diuron EC20 showed no significant reduction when compared to the growth of plants exposed to Irgarol 1051 alone. Despite the addition of the EC20 not eliciting a further significant reduction when compared to the herbicides acting alone for most of the mixtures, the lowest observable significant effect concentration for growth and photosynthetic efficiency decreased to 0.5 ug/L for both herbicides. Irgarol 1051 and Diuron have been shown to occur together in concentrations above 0.5 ug/L, suggesting that seagrasses may be experiencing reduced photosynthetic efficiency and growth as a result.|For more Interactions (Complete) data for 1,3,5-Triazine-2,4-diamine, N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- (6 total), please visit the HSDB record page.

/AQUATIC SPECIES/ After the widespread ban of TBT /tributyltin/, due to its severe impact on coastal biocoenoses, mainly related to its immunosuppressive effects on both invertebrates and vertebrates, alternative biocides such as Cu(I) salts and the triazine Irgarol 1051, the latter previously used in agriculture as a herbicide, have been massively introduced in combined formulations for antifouling paints against a wide spectrum of fouling organisms. Using short-term (60 min) hemocyte cultures of the colonial ascidian Botryllus schlosseri exposed to various sublethal concentrations of copper(I) chloride (LC(50)=281 uM, i.e., 17.8 mg Cu/L) and Irgarol 1051 (LC(50)>500 uM, i.e., >127 mg/L), their immunotoxic effects /were evaluated/ through a series of cytochemical assays previously used for organotin compounds. Both compounds can induce dose-dependent immunosuppression, acting on different cellular targets and altering many activities of immunocytes but, unlike TBT, did not have significant effects on cell morphology. Generally, Cu(I) appeared to be more toxic than Irgarol 1051: it significantly (p<0.05) inhibited yeast phagocytosis at 0.1 uM (approximately 10 ug/L), and affected calcium homeostasis and mitochondrial cytochrome-c oxidase activity at 0.01 uM (approximately 1 ug/L). Both substances were able to change membrane permeability, induce apoptosis from concentrations of 0.1 uM (approximately 10 ug/L) and 200 uM (approximately 50 mg/L) for Cu(I) and Irgarol 1051, respectively, and alter the activity of hydrolases. Both Cu(I) and Irgarol 1051 inhibited the activity of phenoloxidase, but did not show any interactive effect when co-present in the exposure medium, suggesting different mechanisms of action.|/AQUATIC SPECIES/ The toxicity of the antifouling biocides Irgarol 1051, Diuron, Chlorothalonil, Dichlofluanid, Sea-nine 211, Copper pyrithione, Zinc pyrithione, Ziram and Zineb were evaluated on Nitzschia pungens and Artemia larvae. Results showed that EC50 for Irgarol 1051 was 0.586 ug/L was the strongest effect on N. pungens following by Copper pyrithione (4.908 ug/L), Ziram (5.421 ug/L), Zinc pyrithione (5.513 ug/L), Diuron (6.640 ug/L), Zineb (232.249 ug/L), Sea-nine 211(267.368 ug/L), Chlorothalonil (360.963 ug/L) and Dichlofluanid (377.010 ug/L) in 96 hr. In Artemia larvae, the biocides were evaluated the LC50 for larval survivals at 48 hr. Sea-nine 211 and Copper pyrithione were 0.318 and 0.319 mg/L. Chlorothalonil, Zinc pyrithione and Ziram were 2.683, 3.147 and 4.778 mg/L. Irgarol 1051, Diuron, Zineb and Dichlofluanid were 9.734, 30.573, 41.170 and 154.944 mg/L. These results provide baseline data concerning the toxicity of antifouling biocides against marine environment.|/AQUATIC SPECIES/ Macroalgae depend on carbon-concentrating mechanisms (CCMs) to maintain a high photosynthetic activity under conditions of low carbon dioxide (CO(2)) availability. Because such conditions are prevalent in marine environments, CCMs are important for upholding the macroalgal primary productivity in coastal zones. This study evaluated the effects of seven antifouling compounds-chlorothalonil, DCOIT, dichlofluanid, diuron, irgarol, tolylfluanid, and zinc pyrithione (ZnTP)-on the photosynthesis and CCM of sugar kelp (Saccharina latissima (L.)). Concentration-response curves of these toxicants were established using inhibition of carbon incorporation, whereas their effects over time and their inhibition of the CCM were studied using inhibition of O(2) evolution. ...Exposure to all compounds except ZnTP (< 1000 nM) resulted in toxicity to photosynthesis of S. latissima. However, carbon incorporation and O(2) evolution differed in their ability to detect toxicity from some of the compounds. Diuron, irgarol, DCOIT, tolylfluanid, and, to some extent, dichlofluanid inhibited carbon incorporation. Chlorothalonil did not inhibit carbon incorporation but clearly inhibited oxygen (O(2)) evolution.|/AQUATIC SPECIES/ The toxicity of the anti-fouling biocides tributyltin (TBTO), copper, and Irgarol 1051 (irgarol) at nominal concentrations ranging from 10 to 10,000 ug/L was investigated against the speed of encystment and successful formation of a protective cyst of the cercariae of Parorchis acanthus. For all biocide exposures, cercariae had a much slower rate of encystment and reduced cyst formation than controls. Exposure of the snail host Nucella lapillus for 7 days caused complete cessation of cercarial shedding in irgarol-exposed snails but had no effect on cercarial encystment from TBTO and copper-exposed snails. The mechanisms of toxicity of the biocides are briefly discussed.|For more Ecotoxicity Excerpts (Complete) data for 1,3,5-Triazine-2,4-diamine, N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- (37 total), please visit the HSDB record page.

Irgarol 1051's production and use as an antifouling agent in paint(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a structure estimation method(2), indicates that Irgarol 1051 is expected to have moderate mobility in soil(SRC). Volatilization of Irgarol 1051 from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 3.1X10-8 atm-cu m/mole(SRC) based upon its vapor pressure, 6.6X10-7 mm Hg(3), and water solubility, 7 mg/L(4). Irgarol 1051 is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Using the modified Sturm test, Irgarol 1051 is not readily biodegradable(4), indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 145-63,000 in sediment(2-3), indicate that Irgarol 1051 is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 3.1X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 6.6X10-7 mm Hg(5), and water solubility, 7 mg/L(6). Irgarol 1051 was reported to be stable to hydrolysis(7). According to a classification scheme(8), BCFs of 240 and 250 measured in fish(6), suggest bioconcentration in aquatic organisms is high. In marine microcosm studies, Irgarol 1051 had a half-life of 22.4-22.7 days, the major degradation product was 2-methylthio-4-tert-butylamino-6-amino-s-triazine which had a half-life of 21.8-23.6 days(9). The water residence time of Irgarol 1051 was reported as 10.2 years(10). Degradation rates in water and sediment were 0.0054/day and 0.086/year, respectively(10). Photo-degradation half-lives in various natural waters were reported as 1.38-60.72 hours(11-12).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Irgarol 1051, which has a vapor pressure of 6.6X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase Irgarol 1051 is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7 days(SRC), calculated from its rate constant of 2.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase Irgarol 1051 may be removed from the air by wet or dry deposition(SRC).

The rate constant for the vapor-phase reaction of Irgarol 1051 with photochemically-produced hydroxyl radicals has been estimated as 2.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The photo-degradation half-life for Irgarol 1051 in deionized water, ground water and seawater were 103.8, 125.4 and 107.5 minutes, respectively(2). Under aquatic sunlit conditions Irgarol 1051 degraded rapidly(3). Irgarol 1051 was stable to hydrolysis(3).|The photo-degradation half-lives of Irgarol 1051 were measured using artificial light at 300 and 350 nm and under natural conditions in a pond using water from Port of Miami, Miami River, Coconut Grove Marina and distilled deionized water at pH 8 (DDW)(1). The degradation rate was faster in natural waters than in pure water(1).

The BCFs in whole body tissue of sheepshead minnow (Cyprinodon variegatus) were 240 and 250 after exposure to 36 and 3.6 ug/L of Irgarol 1051, respectively(1). According to a classification scheme(2), these BCFs suggest the potential for bioconcentration in aquatic organisms is high. The average bioconcentration for Irgarol 1051 in marine microalgae (Tetraselmis suecica) was reported as 49,400(3).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of Irgarol 1051 can be estimated to be 250(SRC). According to a classification scheme(2), this estimated Koc value suggests that Irgarol 1051 is expected to have moderate mobility in soil. In sediment, log Koc values of 2.16(3) and 2.4-4.8(4) were reported. These correspond to Koc values of 145 and 250-63,000, respectively. A Koc of 3100 in sediment was also reported(5). A log Koc value of 2.7 (Koc 500) was reported in secondary sewage sludge(6).

The Henry's Law constant for Irgarol 1051 is estimated as 3.1X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 6.6X10-7 mm Hg(1), and water solubility, 7 mg/L(2). This Henry's Law constant indicates that Irgarol 1051 is expected to be essentially nonvolatile from water and moist soil surfaces(3). Irgarol 1051 is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

SURFACE WATER: Irgarol 1051 was detected at 0.58-77.0 and 52.3-2218 ng/L in surface water samples collected Mar and Jul 2002, respectively from 3 sites in Port Annapolis and 9 sites on Severn River, MD(1). Irgarol 1051 was detected in marinas, harbors and coastal waters of the Florida Keys, Bermuda and St Croix at 3-294 ng/L(2). The concentration of Irgarol 1051 in surface water samples collected from the Miami River, Biscayne Bay and selected areas of the Florida Keys was reported as <1-182 ng/L(3). In surface water samples collected 2006-2007 from marinas on the island of Oahu, HI, Irgarol 1051 was detected at <17-283 ng/L(4). The maximum reported concentration of Irgarol 1051 in water samples collected from Southern California recreational marinas was 254 ng/L(5).|SURFACE WATER: Irgarol 1051 was detected at 4-190, 52-500, <2 and <2-11 ng/L in samples collected Jul-Sep 1993 from estuary, marine, river and coastal samples of the Southern England coast(1). The average concentration of Irgarol 1051 in surface water samples collected from ports of the Cote d'Azur, France was 88 ng/L with a range of 5 to 280 ng/L(2). Average marina concentrations were 650 ng/L (110-1700 ng/L)(2). Irgarol 1051 concentrations decreased from 145 to 2.5 ng/L in surface water collected Aug 1994 to Apr 1995 from Port d'Ouchy, Lake Geneva, Switzerland(2). In surface water samples collected Apr-Nov 1996 from 7 sites in the Stockholm Archipelago, Irgarol 1051 was detected at 3-130 ng/L(3). In surface water samples collected Jul-Sep 1997 from marinas of the North and Baltic Sea, Irgarol 1051 was reported at 11-440 ng/L(4). Irgarol 1051 was detected at <0.15-0.68 ppb in 15 surface water samples collected Oct 1998 and Jun 1999 from Blackwater Estuary, Essex, UK(5). Irgarol 1051 was detected at 7-543 ng/L in surface water samples collected Jan-Mar 1999 from 7 sites in Conwy Marina, North Wales(6). In seawater samples collected Jul-Aug 1997 from 23 sites in the Seto Inland Sea, Japan, Irgarol 1051 was detected at 7 sites at a concentration of 58.8-142 ng/L(7). Irgarol 1051 was detected at <0.8-267 ng/L in water samples collected in 2002 and 2003 from 8 sites in the port of Osaka, Japan(8). In surface water samples collected July 2007 from Maizuru Bay, Japan, Irgarol 1051 was detected at 0.002-0.018 ug/L(9). Irgarol 1051 was detected in 13 and 73% of samples collected in 2006 and 2009 at respective concentrations of not detected to 23.80 ng/L and not detected to 67.74 ng/L from 45 coastal sites of Korea(10). The concentration of Irgarol 1051 was reported as 1.3-22 ng/L in samples collected in Jun 2012 from 14 streams and small rivers in Germany(11).|... In 2001 we sampled the main rivers and shallow freshwater lakes (Broads) of East Anglia UK for Irgarol 1051, its metabolite GS26575 (2-methylamino-4-tert-butylamino-6-amino-s-triazine) and diuron in order to establish the baseline environmental concentrations of these compounds in freshwater systems of eastern UK and to investigate their possible effects on aquatic plants. Irgarol 1051, GS26575 and diuron were found in water samples collected from 21 locations. The highest concentrations were found in the Norfolk and Suffolk Broads in May. The rivers Great Ouse, Wissey, Bure and Yare also contained all three compounds, as did the Great Ouse Cut-off Channel. ...

Occupational exposure to Irgarol 1051 may occur through dermal contact with this compound at workplaces where Irgarol 1051 is produced or used. Monitoring and use data indicate that the general population is not likely to be exposed to Irgarol 1051. (SRC)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/ALTERNATIVE and IN VITRO TESTS/ In this study, HepG2 cells were exposed to 0.04-40 mg/L Irgarol 1051. Results show that Irgarol 1051 can damage cell morphology and cause a significant decrease in cell viability. Positive staining by Annexin V, caspase-3 activity enhancement, and the damage in cell ultrastructure indicated an apoptotic mode of cell death for 4.0 mg/L Irgarol 1051 treatment. At the same time, caspase-9 was also significantly induced by 0.4 and 4.0 mg/L Irgarol 1051 at 72 hr, which suggests that the intrinsic mitochondria pathway was involved in the apoptosis. The mitochondrial membrane potential decreased significantly after the HepG2 cells were exposed to Irgarol 1051 for 6 and 72 hr. Especially, the translocation of cytochrome c from mitochondria to cytosol was recorded, supporting the idea that the mitochondrial pathway was involved in the apoptosis signal pathways induced by Irgarol 1051. The significantly increased levels of intracellular reactive oxygen species (ROS) and an immediate ROS burst were also recorded. The results here may imply that Irgarol 1051 induces HepG2 cell apoptosis through mitochondrial dysfunction and oxidative stresses. Although it is possible that this chemical has no detrimental effects on human health at the environmentally relevant concentration, it may cause problems to top coastal predators due to bio-accumulation through the food chain.

2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine

The National Pesticide Information Retrieval System (NPIRS) identifies 9 companies with active labels for products containing the chemical cybutryne. To view the complete list of companies, product names and percent cybutryne in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.|Densil CA (Arch Chemials, Inc.): Active ingredient: chlorothalonil 47.0% and 1,3,5-triazine-2,4-diamine, N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- 6.0%.|Irgarol 1071 (BASF Corporation): Active ingredient: 1,3,5-triazine-2,4-diamine, N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- 98.6%.|Copper Pro SCX (Bluewater Marine Paint): Active ingredient: cuprous oxide 67.0% and 1,3,5-triazine-2,4-diamine, N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- 1.96%.|For more Formulations/Preparations (Complete) data for 1,3,5-Triazine-2,4-diamine, N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- (25 total), please visit the HSDB record page.

An automatic method for determining diuron, Irgarol 1051, folpet and dichlofluanid in seawater samples have been developed. This method is based on the on-line coupling of solid-phase extraction (SPE) with a highly crosslinked polymeric sorbent, LiChrolut EN, to liquid chromatography followed by atmospheric pressure chemical ionization (APCI) and mass spectrometry. The operational parameters affecting the APCI interface have been studied in both positive and negative ionization modes. The use of LiChrolut EN in the SPE produced recoveries of over 85% for all the compounds when 100 mL of seawater sample was preconcentrated. Calibration was carried out in both ionization modes and in full-scan and selected-ion monitoring (SIM). The method allowed all the analytes to be detected at 5 ng/L in SIM acquisition mode except folpet, which, because of its low response, could only be detected at 250 ng/L. The method was used to analyze water samples taken from five different marina and fishing ports along the coast of Tarragona, Catalonia (Spain), over a 5-month period. Diuron and Irgarol 1051 were detected and quantified in most samples at concentration levels ranging from 27 to 420 ng/L for diuron and from 15 to 511 ng/L for irgarol 1051.|A method has been developed for the simultaneous determination of antifouling pesticides and some of their degradation products, e.g. dichlofluanid, diuron, demethyldiuron, 1-(3,4-dichlorophenyl)urea, sea-nine, Irgarol 1051 and one of its metabolites (2-methylthio-4-tert-butylamino-s-triazine) in marine sediments. The determination of these compounds in sediment samples was performed by means of methanolic ultrasonic extraction then clean-up on an Isolute ENV+ solid phase extraction (SPE) cartridge. The resulting extract was then analyzed by reversed-phase high-performance liquid chromatography coupled with atmospheric-pressure chemical-ionization mass spectrometry in negative and positive ion modes (HPLC-APCI-MS). Recovery ranged from 54-109% for the antifouling agents and their degradation products. The determination limits for the different compounds varied between 0.2 and 1.6 ug/kg dry sediment. The analytical procedure was successfully applied to the determination of these pesticides and their degradation products in marine sediment samples from different marinas of the Catalan coast. The compounds detected were: diuron, dichlofluanid, demethyldiuron, sea-nine, and Irgarol 1051. The highest concentrations were those of diuron and Irgarol 1051: 136 and 88 ug/kg, respectively.|A comparative study of enzymatic and non-enzymatic labels combined with luminescence detection, developed for immunosensing of pesticide residues (carbaryl, 1-naphthol, Irgarol 1051) in organic media, is presented. Peroxidase and alkaline phosphatase enzymes with fluorogenic (3-p-hydroxyphenylpropanoic acid) and luminogenic (AMPPD derivative) substrates, respectively, were assessed as enzymatic markers. As an alternative, terbium(III) chelate, with time-resolved fluorescence detection, was evaluated as a non-enzymatic label. The best sensitivity was achieved by use of alkaline phosphatase in an immunocomplex capture assay format (I (50) values 0.06, 0.27, and 7.45 ug/L in buffer, 1:1 methanol-buffer, and methanol, respectively). Results were also good (I (50) 1.00 and 6.30 ug/L for water and aqueous-organic mixture, respectively) for Tb(III) chelate in an immobilized conjugate assay format. Use of alkaline phosphatase label to measure carbaryl (100 ng/L) in different spiked river water samples, after solid-phase extraction and analyte elution with an ethyl acetate-methanol mixture, resulted in recoveries ranging from 81 to 98%, with acceptable precision (CV 4-14%, n=4).|A simple multiresidue method has been developed for the determination of five pesticides, commonly used as active ingredients in antifouling paints, in seawater samples. The pesticides studied were: chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile), dichlofluanid (N-dimethyl-N-phenylsulphamide), Sea-Nine 211 (4,5-dichloro-2-n-octyl-4-isothazolin-3-one), Irgarol 1051 (2-methylthio-4-tert.-butylamino-6-cyclopropylamino-s-triazine) and TCMTB (2-thiocyanomethylthiobenzothiazole). The analytes were extracted from 200 mL water samples, using solid-phase extraction. A copolymer with hydrophilic-lipophilic balance was used as sorbent yielding good recoveries (82-95%) for most compounds except dichlofluanid and Sea-Nine 211 (<60%). Large volume injection (10 uL) gas chromatography and electron impact ionization MS (selected ion monitoring mode) detection enabled these compounds to be identified and quantified at the 1.2-3.0 ng/L level. Analysis of samples performed in three marinas in Almeria (Spain) revealed the presence of Irgarol 1051 in all the cases, at concentration levels between 25 and 450 ng/L.|For more Analytic Laboratory Methods (Complete) data for 1,3,5-Triazine-2,4-diamine, N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- (15 total), please visit the HSDB record page.

A method is presented for the extraction, preconcentration, and determination of two commonly used booster biocides, Irgarol 1051 and diuron, in samples of muscle and liver tissues from Mugil cephalus by microwave-assisted extraction (MAE) followed by SPE for the preconcentration and cleanup step, coupled with LC/MS/MS. The optimum conditions for MAE were established as power 200 W and irradiation time 4 min. Using these conditions, the LOD was 0.13 ng/g for diuron and 0.10 ng/g for Irgarol 1051. The recoveries calculated at three concentration levels (0.5, 5, and 50 ng/g) were greater than 74%. Repeatability was less than 7.5% and reproducibility less than 12.7%. The optimized method was used to monitor these compounds in M. cephalus from different harbors of Gran Canaria Island. The samples were collected bimonthly and processed following the optimized method. High levels of Irgarol 1051(6.9 +/- 1.03 ng/g) were found in the liver, while diuron was undetected. However, diuron was found in the muscle (1.41 +/- 0.45 ng/g). The proposed sentinel organism could be used in tropical and subtropical regions to continuously biomonitor for booster biocides over long periods of time. This technique could be a useful tool for improving the management of ocean and coastal waters.|A mild, low-temperature analytical approach based on sonication assisted extraction coupled with HPLC electrospray ionization triple quadrupole tandem mass spectrometry has been developed for the simultaneous qualitative and quantitative determination of the four Irgarol-related s-triazine species, namely Irgarol-1051, M1, M2 and M3, in coastal sediments and Green-lipped mussel samples. Mild extraction conditions were necessary for the preservation of the thermally unstable M2. The Multiple Reaction Monitoring (MRM) mode of detection by ESI-MS/MS enabled reliable qualitative identification and sensitive quantitative determination of those s-triazines. This determination method was applied to evaluate the degree of Irgarol-1051 contamination in the sediments and biota of the coastal environment of Hong Kong - one of the busiest maritime ports in the world. All the four s-triazine species were observed in all of the samples. This is the first time that the newly identified M2 and M3 are detected in coastal sediments and biota tissues.

Algistats, Herbicides|Pesticides -> Fungicides -> Herbicides -> Anti-fouling agents

Irgarol has known environmental transformation products that include Irgarol-descyclopropyl.