Abstracts
Dichlofluanid
CAS No. 1085-98-9
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Adverse Effects

ACTIVITY: Wood Preservative, Antifoulant, Fungicide, Acaricide

CAS Name: 1,1-dichloro-N-[(dimethylamino)sulfonyl]-1-fluoro-N-phenylmethanesulfenamide

Structure:

 

Reports available from
The National Technical Information Service
(NTIS)

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Order No. Title Keywords

NTIS/OTS0543905

EPA/OTS; Doc #88-920006907

1992 - INITIAL SUBMISSION: BAY 47531 (DICHLOFLUANID) GENERATION TESTS WITH RATS WITH ATTACHMENTS AND COVER LETTER DATED 08-24-92

FARBENFABRIKEN BAYER AG

MILES INC
BAY 47531 (DICHLOFLUANID)
HEALTH EFFECTS
REPRODUCTION/FERTILITY EFFECTS
COMBINED TERATOGENICITY/REPRODUCTIVE EFFECTS
MAMMALS
RATS
ORAL
DIET
CAS Registry Numbers: 1085-98-9

NTIS/OTS0545057

EPA/OTS; Doc #88-920006458

1992 - INITIAL SUBMISSION: TOXICITY STUDIES WITH DICHLOFLUANID & TOLYLFLUANID IN RATS, MICE, AND DOGS WITH COVER LETTER DATED 09-21-92

MILES INC
DICHLOFLUANID & TOLYLFLUANID
HEALTH EFFECTS
CHRONIC TOXICITY
COMBINED CHRONIC TOXICITY/CARCINOGENICITY
MAMMALS
DOGS
RATS
MICE
REPRODUCTION/FERTILITY EFFECTS
TERATOGENICITY
RABBITS

CAS Registry Numbers:
731-27-1
1085-98-9

NTIS/BIBRA380 6p

1990 - BIBRA Toxicity Profile of dichlofluanid.

British Industrial Biological Research Association, Carshalton (England).

The BIBRA Toxicity Profile is a comprehensive yet concise review of the toxicological data on the profiled chemical. All studies identified have been carefully evaluated (using primary data sources wherever possible), but only the data most pertinent to hazard assessment are included. Information is summarized, where available, on the effects in man, as well as other species, and studies relating to the principal exposure routes are given precedence. The Profile is divided into the following main sections: Summary, Identification, Local Effects (including skin, eye and respiratory tract irritation), Sensitization and Intolerance, General Systemic Effects (including single and repeated administration), Reproductive Toxicity, Carcinogenicity and Other Genotoxicity.

Keywords: Dichlofluanid


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1991455&dopt=Abstract

Environ Mol Mutagen 1991;17(1):20-6

Comment in:

Genotoxicity of the fungicide dichlofluanid in seven assays.

Heil J, Reifferscheid G, Hellmich D, Hergenroder M, Zahn RK.

Department of Environmental and Molecular Genotoxicity, Johannes Gutenberg University of Mainz, Germany.

Seven different endpoints for detection of genotoxicity have been used to demonstrate the DNA-altering properties of Dichlofluanid, a fungicide commonly used in viticulture pest control. Each endpoint (DNA synthesis inhibition test, alkaline viscosimetry, umu-test, alkaline filter elution, FADU-test, 32P-postlabeling, and electron microscopy) shows clear evidence of genotoxicity. These data indicate that application of the fungicide dichlofluanid may be mutagenic and/or carcinogenic for exposed humans.

PMID: 1991455 [PubMed - indexed for MEDLINE]


Toxicology; Volume 204, Issues 2-3 , 15 November 2004, Pages 97-107

Oxidative damages in isolated rat hepatocytes treated with the organochlorine fungicides captan, dichlofluanid and chlorothalonil

Toshihide Suzuki, , Hisao Nojiri, Hideo Isono and Takafumi Ochi

Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1 Sagamiko-machi, Tsukui-gun, Kanagawa 199-0195, Japan

The cytotoxicity and lipid peroxidative potency of the organochlorine fungicides captan (N-(trichloromethylthio)-4-cyclohexene-1,2-dicarboximide), dichlofluanid (N-dichlorofluoromethylthio-N?N?-dimethyl-N-phenylsulfamide) and chlorothalonil (2,4,5,6-tetrachloro-isophthalonitrile) were studied in isolated rat hepatocytes. These fungicides induced cytotoxicity and lipid peroxidation in a dose- and time-dependent manner. Considerable cytotoxicity and lipid peroxidation occurred after cells were treated with 25 ?M and more of fungicide. The phosphatidylcholine hydroperoxide (PCOOH) content increased more than 300 times by captan (250–1000 ?M), 400 times by dichlofluanid (250–1000 ?M) and 20 times by chlorothalonil (25–1000 ?M) after 1 h of incubation, as compared with untreated control. Significant cytotoxicity occurred after
20 min (captan),
30 min (dichlofluanid)
and
60 min (chlorothalonil)
of incubation and lipid peroxidation was induced prior to cytotoxicity. The antioxidant ?-tocopherol and cytochrome P450 inhibitor SKF-525A effectively prevented cytotoxicity and lipid peroxidation. Our results suggest that metabolites of these fungicides produced by the microsomal cytochrome P450 system, induced membrane phospholipid peroxidation that caused cytotoxicity.


Environment International; Volume 30, Issue 2 , April 2004, Pages 235-248

Worldwide occurrence and effects of antifouling paint booster biocides in the aquatic environment: a review

I. K. Konstantinou, and T. A. Albanis

Laboratory of Environmental Technology, Department of Chemistry, University of Ioannina, 45110, Ioannina, Greece

Organic booster biocides were recently introduced as alternatives to organotin compounds in antifouling products, after restrictions imposed on the use of tributyltin (TBT) in 1987. Replacement products are generally based on copper metal oxides and organic biocides. This ban has led to an increase in alternative coating products containing the above biocides. The most commonly used biocides in antifouling paints are: Irgarol 1051, diuron, Sea-nine 211, dichlofluanid, chlorothalonil, zinc pyrithione, TCMS (2,3,3,6-tetrachloro-4-methylsulfonyl) pyridine, TCMTB [2-(thiocyanomethylthio) benzothiazole], and zineb. Since 1993, several studies have demonstrated the presence of these biocides in European coastal environment as a result of their increased use. More recently, the presence of these biocides was also revealed in waters from Japan, United States, Singapore, Australia and Bermuda. This paper reviews the currently available data on the occurrence of these biocides in the aquatic environment. Some data dealing with the environmental fate, partitioning, behaviour and risk assessment of antifouling paint booster biocides are also reported in order to discuss the detected levels of contamination.

EXCERPT: Dichlofluanid water concentrations detected in Greece [Sakkas et al., 2002 (a)] were lower than in Spanish ports and marinas [Martinez et al., 2000 (b)], however [Voulvoulis et al., 2000 (c)] did not found any contamination of waters in Blackwater Estuary (UK) but relatively high concentration were monitored in sediments (Table 6). In addition, the study performed by [Thomas et al., 2000 (d)] showed negligible concentrations in marina water and sediments. [Ferrer and Barceló, 1999 (e)] also reported the absence of dichlofluanid in waters collected from Mediterranean marinas. On the contrary, the study of [Martínez and Barceló, 2001 (f)] revealed the presence of dichlofluanid in sediments from Spanish marinas in the Mediterranean Sea. The concentrations of dichlofluanid were greatest during the months June–October (after painting use) showing a decline during the winter period, though measurable amounts of biocides remain in the sediment during that time [Albanis et al., 2002 (g)and Voulvoulis et al., 2000 (c) ]. This trend shows the importance of the type and source of inputs and the prevailing weather conditions. In wind period, the antifouling paint application rate is low, the boats are out of the water during that time and only residual antifouling compounds from previous year's application is strongly bound to sediment particles. Fresh application led to an increase in period after boating activity and with less rainfall, higher concentrations were detected in the coastal sediments.
Dichlofluanid is much less soluble in water than Irgarol 1051 (<2 mg/l) and has a high octanol/water partition coefficient (log Kow=3.7); thus, it was found the most strongly bound biocide in sediment compared to Irgarol 1051, chlorothalonil and diuron [Voulvoulis et al., 2000 (c)]and Voulvoulis et al., 2002b
(h) ]. The lower contamination of water samples and the relative high concentrations detected in sediments after boating season indicate that this biocide also justify the above assumption. Results from [Voulvoulis et al., 2002b (h) ] demonstrated that dichlofluanid has a stronger adsorption characteristics and was predicted to bind more strongly to sediments than Irgarol or chlorothalonil. The photodegradation half-life in natural seawater was 53 h [Sakkas et al., 2001 (i)] and a half-life of 18 h was reported on a bioassay method [Callow and Finlay, 1995 (j)]. The main degradation products occurred from photodegradation, hydrolysis and anaerobic degradation were N,N-dimethyl-N?-phenyl-sulfamide (DMSA), n-dichlorofluoromethylthio-aniline and aniline [Sakkas et al., 2001 (i)and Thomas et al., 2003 (k)].

References:
(a)
V.A. Sakkas, I.K. Konstantinou, D.A. Lambropoulou and T.A. Albanis, Survey for the occurrence of antifouling paint booster biocides in the aquatic environment of Greece. Environ. Sci. Pollut. Res. 9 5 (2002), pp. 327–332.

(b) K. Martinez, I. Ferrer and D. Barceló, Part-per-trillion level determination of antifouling pesticides and their byproducts in seawater samples by off-line solid-phase extraction followed by high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J. Chromatogr. A 879 (2000), pp. 27–37.

(c) N. Voulvoulis, M.D. Scrimshaw and J.N. Lester, Occurrence of four biocides utilised in antifouling paints, as alternatives to organotin compounds, in waters and sediments of a commercial estuary in the UK. Mar. Pollut. Bull. 40 (2000), pp. 938–946.

(d) K.V. Thomas, S.J. Blake and M.J. Waldock, Antifouling paint booster biocide contamination in UK Marine sediments. Mar. Pollut. Bull. 40 (2000), pp. 739–745.

(e) I. Ferrer and D. Barceló, Simultaneous determination of antifouling herbicides in marina water samples by on-line solid-phase extraction followed by liquid chromatography-mass spectroscopy. J. Chromatogr. A 854 (1999), pp. 197–206.

(f) K. Martínez and D. Barceló, Determination of antifouling pesticides and their degradation products in marine sediments by means of ultrasonic extraction and HPLC-APCI-MS. Fresenius' J. Anal. Chem. 370 (2001), pp. 940–945.

(g) T.A. Albanis, D.A. Lambropoulou, V.A. Sakkas and I.K. Konstantinou, Antifouling paint booster biocide contamination in Greek marine sediments. Chemosphere 48 (2002), pp. 475–485.

(h) N. Voulvoulis, M.D. Scrimshaw and J.N. Lester, Partitioning of selected antifouling biocides in the aquatic environment. Mar. Environ. Res. 53 (2002), pp. 1–16.

(i) V.A. Sakkas, I.K. Konstantinou and T.A. Albanis, Photodegradation study of the antifouling booster biocide dichlofluanid in aqueous media by gas chromatographic techniques. J. Chromatogr. A 930 (2001), pp. 135–144.

(j) M.E. Callow and J.A. Finlay, A simple method to evaluate the potential for degradation of antifouling biocides. Biofouling 9 (1995), pp. 239–249.

(k) K.V. Thomas, M. McHugh, M. Hilton and M. Waldock, Increased persistence of antifouling paint biocides when associated with paint particles. Environ. Pollut. 123 (2003), pp. 153–161.


Aquatic Toxicology; Volume 66, Issue 4 , 10 March 2004, Pages 427-444

Environmental risk limits for antifouling substances

Annemarie P. van Wezel, and P. van Vlaardingen

Centre for Substances and Risk Assessment, National Institute of Public Health and the Environment, P.O. Box 1, 3720 BA, Bilthoven, The Netherlands

In 1989, the EU restricted the use of tributyl-tin (TBT) and the International Maritime Organisation (IMO) decided for a world-wide ban on TBT in 2003. As a replacement for TBT, new antifouling agents are entering the market. Environmental risk limits (ERLs) are derived for substances that are used as TBT-substitutes, i.e. the compounds Irgarol 1051, dichlofluanid, ziram, chlorothalonil and TCMTB. ERLs represent the potential risk of the substances to the ecosystem and are derived using data on (eco)toxicology and environmental chemistry. Only toxicity studies with endpoints related to population dynamics are taken into account.
For Irgarol 1051 especially plants appear to be sensitive; the mode of action is inhibition of photosynthetic electron transport. Despite the higher sensitivity of the plants, the calculated ERL for water based on plants only is higher than the ERL based on all data due to the lower variability in the plant only dataset. Because there is a mechanistic basis to state that plants are the most sensitive species, we propose to base the ERL for water on the plants only dataset. As dichlofluanid is highly unstable in the water phase, it is recommended to base the ERL on the metabolites formed and not on the parent compound.
No toxicity data of the studied compounds for organisms living in sediments were found, the ERLs for sediment are derived with help of the equilibrium partitioning method. For dichlofluanid and chlorothalonil the ERL for soil is directly based on terrestrial data, for Irgarol 1051 and ziram the ERL for soil is derived using equilibrium partitioning.

http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12946890&dopt=Abstract

Water Res. 2003 Oct;37(17):4091-8.
 
Combined toxicity effects of MTBE and pesticides measured with Vibrio fischeri and Daphnia magna bioassays.

Hernando MD, Ejerhoon M, Fernandez-Alba AR, Chisti Y.

Department of Analytical Chemistry, University of Almeria, 04120 Almeria, Spain.

Methyl-tert-butyl ether (MTBE), a fuel oxygenate that is added to gasoline, commonly contaminates aquatic systems, many of which are already contaminated with pesticides. The toxic effects (EC(50) value) of several pure pesticides (Diuron, Linuron, Dichlofluanid, Sea nine, Irgarol and tributyltin (TBT)) were measured and compared with the EC(50) value of the pesticide mixed with MTBE, using the Vibrio fischeri and Daphnia magna acute toxicity assays. The interaction between chemicals was evaluated in terms of the effects of mixing on the EC(50) value (i.e. the concentration (mg/L) of a compound or mixture that is required to produce a 50% change in a toxic response parameter) and the time required to generate the toxic response. Presence of MTBE enhanced the EC(50) value of several pesticides (Diuron, Dichlofluanid, TBT and Linuron) and/or the toxic response manifested more rapidly than with pure pesticides. Toxicity enhancements were quite substantial in many cases. For example, the presence of MTBE increased the toxicity of Diuron by more than 50% when tested with the V. fischeri assay (5, 15 and 30 min exposure). Also, the toxic response manifested itself within 5 min whereas without the MTBE the same response arose in 30 min. Presence of MTBE increased the toxicity of Dichlofluanid by 30% when measured with the D. magna assay. Toxicities of only two pesticides (Sea nine and Irgarol) were not raised by the presence of MTBE.

PMID: 12946890 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12748042&dopt=Abstract

Toxicology. 2003 Jun 3;188(1):73-81.
 
Determination of the immunotoxic potential of pesticides on functional activity of sheep leukocytes in vitro.

Pistl J, Kovalkovicova N, Holovska V, Legath J, Mikula I.

Department of Microbiology and Immunology, University of Veterinary Medicine, 041 81, Kosice, Slovakia. pistl@uvm.sk

The effect of eight pesticides with different chemical structure (atrazine, bentazone, chloridazone, dichlofluanid, endosulfan, MCPA, simazine, triallate) on sheep peripheral blood phagocytes and lymphocytes was examined under in vitro conditions by iodo-nitro-tetrazolium reductase test and leukocyte migration-inhibition assay. The pesticides, dissolved in DMSO, were tested at the concentrations of 10(-1)-10(-6) M. The significant suppression of metabolic activity of phagocytic cells was registered after exposure to dichlofluanid (10(-1)-10(-3) M), endosulfan, simazine and triallate (10(-1) M). The significant cytotoxic effect (the decrease of spontaneous migration of leukocytes) was registered for bentazone, dichlofluanid, endosulfan and MCPA (10(-1) M); chloridazone (10(-1) M-10(-2) M) and triallate (10(-1)-10(-5) M). The significant immunotoxic effect (the decrease of lymphocyte activation with PHA) was observed for atrazine (10(-1)-10(-2) M); bentazone (10(-2)-10(-4) M); dichlofluanid, endosulfan (10(-2)-10(-3) M); MCPA (10(-2)-10(-6) M) and simazine (10(-1)-10(-4) M). Three of the pesticides tested suppressed both, the metabolic activity of phagocytes and mitogenic activation of lymphocytes (dichlofluanid, endosulfan and simazine). Triallate suppressed the metabolic activity of phagocytes and showed a strong cytotoxic effect. Pesticides atrazine, bentazone and MCPA influenced the mitogenic activation of lymphocytes and chloridazone showed a significant cytotoxic effect. The different chemical structure of pesticides influenced the metabolic activity of phagocytic cells as well as mitogenic activation of lymphocytes to various intensity.


PMID
: 12748042 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12805969&dopt=Abstract

Scientific World Journal. 2002 Apr 25;2(4):1115-20.

Toxicity of single and mixed contaminants in seawater measured with acute toxicity bioassays.

Fernandez-Alba AR, Piedra L, Mezcua M, Hernando MD.

Different types of organic pollutants commonly detected in seawater have been evaluated by acute toxicity bioassays. Vibrio fischeri, Daphnia magna, and Selenastrum capricornotum were selected to test toxic effects of individual compounds and mixtures of these compounds, obtaining EC50 values in the range of 0.001 to 28.9 mg/l. In the case of mixtures, synergistic toxic responses were seen for a clear majority of the cases (>60%). Mixtures containing methyl-tertiary-butyl ether (MTBE) exhibit accelerated processes that result in a change in concentration required to produce a toxic effect; for example, in the case of mixtures containing MTBE and Diuron and Dichlofluanid.


PMID: 12805969 [PubMed - in process]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12146627&dopt=Abstract

Chemosphere 2002 Aug;48(5):475-85

Antifouling paint booster biocide contamination in Greek marine sediments.

Albanis TA, Lambropoulou DA, Sakkas VA, Konstantinou IK.

Department of Chemistry, University of Ioannina, Greece. talbanis@cc.uoi.gr

Organic booster biocides were recently introduced as alternatives to organotin compounds in antifouling products, after restrictions imposed on the use of tributyltin in 1987. In this study, the concentrations of three biocides commonly used as antifoulants, Irgarol 1051 (2-methylthio-4-tertiary-butylamino-6-cyclopropylamino-s-triazine), dichlofluanid (N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenyl sulphamide) and chlorothalonil (2,4,5,6-tetrachloro isophthalonitrile) were determined in sediments from ports and marinas of Greece. Piraeus (Central port, Mikrolimano and Pasalimani marinas), Thessaloniki (Central port and marina), Patras (Central port and marina), Elefsina, Igoumenitsa, Aktio and Chalkida marinas were chosen as representative study sites for comparison with previous monitoring surveys of biocides in coastal sediments from other European countries. Samples were collected at the end of one boating season (October 1999), as well before and during the 2000 boating season. All the compounds monitored were detected at most of sites and seasonal dependence of biocide concentrations were found, with maxima during the period June-September, while the winter period (December-February) lower values were encountered. The concentrations levels ranged from 3 to 690 ng/g dw (dry weight). Highest levels of the biocides were found in marinas (690, 195 and 165 ng/g dw, for Irgarol, dichlofluanid and chlorothalonil respectively) while in ports lower concentrations were observed. Antifouling paints are implicated as the likely sources of biocides since agricultural applications possibly contributed for chlorothalonil and dichlofluanid inputs in a few sampling sites.

PMID: 12146627 [PubMed - in process]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11767737&dopt=Abstract

Mar Environ Res. 2002 Feb;53(1):1-16.

Partitioning of selected antifouling biocides in the aquatic environment.

Voulvoulis N, Scrimshaw MD, Lester JN.

Environmental Processes and Water Technology Group, The T. H. Huxley School of Environment, Earth Sciences and Engineering, Imperial College of Science, Technology and Medicine, London SW7 2PE, UK.

Following a ban on the use of tributyltin in antifouling products on small boats, a number of organic booster biocides have been utilised in conjunction with copper in antifouling paints as alternative treatments. The fate of organic compounds in the aquatic environment is closely linked to their partitioning between aqueous media and sediment. In this study, experiments were designed to investigate the partitioning and sorptive behaviour of Irgarol 1051, chlorothalonil, dichlofluanid and diuron in the aquatic environment. Factorial experiments were undertaken to determine the importance of pH, particulate matter concentration and salinity to their sorption. A Mackay fugacity model was also applied. Results demonstrated that dichlofluanid had the stronger adsorption characteristics and was predicted to bind more strongly to sediments than Irgarol or chlorothalonil. Diuron exhibited the least preference for sorptive behaviour. Sorption appeared to be enhanced by increased suspended matter, whilst salinity does not seem to play a significant role in the partitioning behaviour of these biocides.

PMID: 11767737 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11804510&dopt=Abstract

J Agric Food Chem 2002 Jan 30;50(3):441-8

Assessment of the stability of pesticides during cryogenic sample processing. 1. Apples.

Fussell RJ, Jackson Addie K, Reynolds SL, Wilson MF.

Central Science Laboratory, Sand Hutton, York YO41 1LZ, United Kingdom.

An assessment of the stability of a large number (106) of pesticides and related compounds during the cryogenic sample processing of apples has been undertaken. For the first time the procedure included an assessment of the losses during the freezing of the fruits, prior to processing. The stability of each pesticide during processing was assessed by comparing the mean recovery for the laboratory-spiked samples with the mean "survival" of the pesticides in cryogenically processed samples. The results clearly demonstrate that the vast majority, 94 of 106, of pesticides were stable during cryogenic processing. Of particular importance was that losses of several pesticides [bitertanol (95%), heptenophos (50%), isofephos (40%), and tolylfluanid (48%)] reported to occur during ambient processing of apples did not occur during cryogenic processing. Losses of dichlofluanid (54%), chlozolinate (22%), and etridiazole (40%), previously reported to occur during ambient processing of apples, were reduced to barely significant levels (10, 17, and 14%, respectively) by cryogenic processing. Small apparent losses for a few of the compounds were attributable to analytical and sample handling difficulties, rather than to losses during processing, and need further investigation.

PMID: 11804510 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12391808&dopt=Abstract

Environ Sci Pollut Res Int. 2002;9(5):327-32.

Survey for the occurrence of antifouling paint booster biocides in the aquatic environment of Greece.

Sakkas VA, Konstantinou IK, Lambropoulou DA, Albanis TA.

Department of Chemistry, University of Ioannina, Ioannina 45110, Greece.

Since the restriction imposed by European Union regulations on the use of TBT-based antifouling paints on boats below 25 m in length, new terms have been introduced in the 'small boat' market. Replacement products are generally based on copper metal oxides and organic biocides. Several studies have demonstrated the presence of these biocides in European ports and marinas of Spain, France, Germany and the United Kingdom. An extended survey of the antifouling biocides chlorothalonil, dichlofluanid, irgarol 1051 and sea-nine 211 was carried out in Greek ports and marinas of high boating activities from October 1999 to September 2000. The sampling sites were: Piraeus, Elefsina, Thessaloniki, Patras, Chalkida, Igoumenitsa, and Preveza (Aktio). The extraction of these compounds from the seawater samples was performed off-line with C18 solid phase extraction (SPE) disks while the determination was carried out with gas chromatography coupled to electron capture (ECD), thermionic (FTD) and mass spectroscopy (MS) detectors. The concentration levels of biocides were higher during the period from April to October. This seasonal impact depends on the application time of antifouling paints and mimic trends in the seasonal distribution of biocides in other European sites.


PMID: 12391808 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11681571&dopt=Abstract

J Chromatogr A 2001 Sep 28;930(1-2):135-44

Photodegradation study of the antifouling booster biocide dichlofluanid in aqueous media by gas chromatographic techniques.

Sakkas VA, Konstantinou LK, Albanis TA.

Department of Chemistry, University of Ioannina, Greece.

The aquatic photochemical behavior of the biocide dichlofluanid has been studied under natural sunlight conditions as well as under artificial solar irradiation in different types of natural waters (sea, river and lake water) as well as in distilled water. In order to examine the effect of dissolved organic matter (DOM), the photodegradation of the tested biocide was investigated also in the presence of various concentrations of humic and fulvic acids. It was found that the photodegradation proceeds via first-order reaction in all cases and that the presence of various concentrations of DOM inhibits the photolysis reaction. Kinetic experiments are monitored with GC-ECD with half-lives varied between 8 and 83 h. The major photodecomposition products identified by GC-MS were dichlorofluoromethane, aniline, and DMSA. Based on this byproduct identification a possible degradation pathway is proposed for the photolysis of dichlofluanid in aqueous media.

PMID: 11681571 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11424731&dopt=Abstract

Environ Technol 2001 May;22(5):543-52

Occurrence of antifouling biocides in the Spanish Mediterranean marine environment.

Martinez K, Ferrer I, Hernando MD, Fernandez-Alba AR, Marce RM, Borrull F, Barcelo D.

Department of Environmental Chemistry, IIQAB-CSIC, 08034 Barcelona, Spain.

A compilation of the results of a monitoring program of the recently used antifouling pesticides diuron (3-(3,4-dichlorophenyl)-1,1-dimethylurea), Irgarol 1051 (2-methylthio-4-tertiary-butylamino-6-cyclopropylamino-s-teiazine), seanine 211 (4,5-dichloro-2-n-octyl-4-isothazolin-3-one), chlorothalonil (2,4,5,6-tetrachloro-isophthalonitrile), dichlofluanid (N'-dimethyl-N-phenylsulphanamide), TCMTB ((2-thiocyanomethylthio) benzothiazole), and three degradation products demethyldiuron (3-(3,4-dichlorophenyl)-1-methylurea),3,4-dichlorophenylurea and 2-methylthio-4-tert-butylamino-s-triazine (Irgarol degradation product) that was carried out between April 1996 and February 2000 in enclosed seawaters from Catalonia and Almeria (Spanish Mediterranean coast) is reported. Nine points were sampled along the Catalan coast: Barcelona Olympic port, Masnou, Blanes, Sant Carles de la Rapita, Tarragona, Cambrils and Salou marinas as well as the Cambrils and Tarragona fishing harbors and in marinas and ports from Almeria: Aguadulce port, Almeria port, Almerimar fishing harbour and Almerimar marina. The analytical methodologies were based on Solid Phase Extraction followed by liquid chromatography (LC) or gas chromatography (GC) coupled to a mass spectrometry (MS) or -Diode Array Detector. The main pollutants found in the sampled points were diuron and Irgarol 1051 that were detected at concentrations up to 2.19 micrograms l-1 and 0.33 microgram l-1, respectively. On the other hand, seanine 211 was found at the highest concentration (up to 3.7 micrograms l-1) during the summer of 1999. Low concentrations of dichlofluanid and the above mentioned degradation products were detected for the first time in the Spanish coasts. Chlorothalonil, TCMTB were not found at concentrations higher than 1 and 20 ng l-1 respectively which were the limit of determination (LOD) of the method for these compounds. In general the contamination at the different marinas is higher at the end of spring and in summer where the boating activity is also higher. This paper shows for the first time that the contamination by the new antifouling pesticides in Spanish coastline, basically marinas and fishing harbours, is permanent along the whole calendar year. So, preventive actions by the harbour authorities will be needed in the near future in order to monitor and control the levels and effects of the new antifouling biocides in the marine environment.

PMID: 11424731 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11057691&dopt=Abstract

Chemosphere 2000 Nov;41(10):1637-42

Yeasts as a model for assessing the toxicity of the fungicides Penconazol, Cymoxanil and Dichlofluanid.

Ribeiro IC, Verissimo I, Moniz L, Cardoso H, Sousa MJ, Soares AM, Leao C.

Departamento de Biologia, Centro de Ciencias do Ambientie, Universidade do Minho, Braga Codex, Portugal.

In the present work the sensitivity of yeast strains of Kluyveromyces marxianus, Pichia anomala, Candida utilis, Schizosaccharomyces pombe and Saccharomyces cerevisiae, to the fungicides cymoxanil, penconazol, and dichlofluanid, was evaluated. Dichlofluanid induced the most negative effects, whereas penconazol in general was not very toxic. Overall, our results show that the parameters IC50 for specific respiration rates of C. utilis and S. cerevisiae and C(D) for cell viability of S. cerevisiae can be applied to quantify the toxicity level of the above compounds in yeast. Hence, could be explored as an alternative or at least as a complementary test in toxicity studies and, therefore, its potential for inclusion in a tier testing toxicity test battery merits further research.

PMID: 11057691 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10552381&dopt=Abstract

J Agric Food Chem 1999 Mar;47(3):858-61

Fungicide residues in strawberry processing.

Will F, Kruger E.

Department of Wine Analysis and Beverage Research and Department of Fruit Growing, Research Institute Geisenheim, P.O. Box 1154, D-65358 Geisenheim, Germany. will@geisenheim.fa.fh-wiesbaden.de

The fate of three fungicides (dichlofluanid, procymidone, and iprodione) applied under field conditions was studied during strawberry processing to juice, wine, and jam. An untreated control was compared to raw material treated with fungicides according to recommended doses and to a sample with 6-fold higher application rates. The highest residue values were found in the pomace after pressing. Residue values in readily produced juices and fruit wines were very low and did not exceed legally required maximum residue levels. Generally, processing steps such as pressing and clarification diminished fungicide residues from 50 to 100%. If the whole fruit is processed, as in fruit preparations or jam, the residue levels remain higher due to missing processing steps.

PMID: 10552381 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9325584&dopt=Abstract

J AOAC Int 1997 Sep-Oct;80(5):1091-7

Analyses of chlorothalonil and dichlofluanid in greenhouse air.

Egea Gonzalez FJ, Castro Cano ML, Martinez Vidal JL, Martinez Galera M.

Universidad de Almeria, Departamento de Quimica Analitica, Spain.

A method to sample and analyze chlorothalonil and dichlofluanid in greenhouse air was evaluated. Analysis was performed by gas chromatography with electron capture detection and gas chromatography-mass spectrometry. Solid sorbents such as Chromosorb 102, Porapak R, Supelpak-2, Amberlite XAD-2, Amberlite XAD-4, and polyurethane foam were studied. The use of Soxhlet extraction and solvent desorption with sonication to desorb the pesticides from these sorbents were compared. A procedure to generate atmospheres containing known concentrations of these fungicides was established to study sorption capacity and sampling conditions. Breakthrough and storage of pesticides also were studied. Dissipation of analytes in a 24 h period after application was studied by using personal samplers in a field experiment.

PMID: 9325584 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9177013&dopt=Abstract

J Environ Sci Health B 1997 May;32(3):411-28

[Ovarian activity of Drosophila melanogaster Meigen (Diptera), during a chronic intoxication with four fungicides: anatomical and cytological study]

[Article in French]

Marchal-Segault D, Lauge G.

Laboratoire Reproduction, Developpement de l'Insecte, Universite de Paris Sud, Orsay, France.

[[FAN Note: Euparene is a synonym for Dichlofluanid]]

Two types of reactions were observed on the alteration of Drosophila vitellogenesis by the four fungicides used in this study. Dithane M45 resulted in stimulation associated with egg retention. However, the other three fungicides (Benlate, Bouillie bordelaise and Euparene) resulted in inhibition to a varying degree. Although the inhibition was comparatively limited due to Benlate it induced an egg retention. The inhibition was very high due to Bouillie bordelaise and Euparene. With Bouillie bordelaise an egg retention occured together with the reduction of vitellogenesis and caused an increase in the rate of the follicle resorption. The latter depended on the duration of treatment. With Euparene, no egg retention was observed and the toxicity was only noticed on vitellogenesis.


PMID: 9177013 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9084885&dopt=Abstract

Biol Pharm Bull 1997 Mar;20(3):271-4

Cytotoxicity of organochlorine pesticides and lipid peroxidation in isolated rat hepatocytes.

Suzuki T, Komatsu M, Isono H.

Faculty of Pharmaceutical Sciences, Teikyo University, Kanagawa, Japan.

The cytotoxicity and lipid peroxidation of pesticides containing a halogen group were examined in isolated rat hepatocytes. We examined 9 pesticides of 3 different representative chemical families, chlorinated aromatic fungicides (pentachlorophenol (PCP), pentachloronitrobenzene (PCNB), chlorothalonil, fthalide), polyhaloalkylated thio fungicides (dichlofluanid, captan) and diphenyl ether herbicide (2,4-dichlorophenyl 4-nitrophenyl ether (NIP), 4-nitrophenyl2,4,6-trichlorophenyl ether (CNP), chlomethoxynil). The contents of the hydroperoxides in phospholipid, phosphatidylcholine hydroperoxide (PCOOH) and phosphatidylethanolamine hydroperoxide (PEOOH) were determined by the HPLC-chemiluminescence (CL-HPLC) method, which is sensitive and specific for lipid hydroperoxide. Chlorothalonil, dichlofluanid and captan were the most potent cytotoxicants evaluated by lactate dehydrogenase (LDH) leakage. PCP, NIP and CNP exhibited intermediate cytotoxicity. PCNB, fthalide and chlomethoxynil showed low cytotoxicity. The cellular phospholipid hydroperoxide (PCOOH and PEOOH) levels were remarkably increased by chlorothalonil (PCOOH, 23 times and PEOOH, 7 times), dichlofluanid (PCOOH, 523 times and PEOOH, 22 times) and captan (PCOOH, 518 times and PEOOH, 16 times) as compared with the control group. The PCOOH content was slightly increased by PCP (4.8 times) and NIP (6.3 times), whereas the other 4 pesticides did not change the phospholipid hydroperoxide level. Severe cytotoxicity was observed with a remarkable increase of phospholipid hydroperoxide by chlorothalonil, dichlofluanid and captan.

PMID: 9084885 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7758314&dopt=Abstract

Contact Dermatitis 1995 Feb;32(2):116-7

No Abstract available

Allergic contact dermatitis from dichlofluanid.

Hansson C, Wallengren J.

Department of Occupational Dermatology, University of Lund, University Hospital, Sweden.

PMID: 7758314 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=8368870&dopt=Abstract

Arch Environ Contam Toxicol 1993 Aug;25(2):271-8

Effects of pesticides on isolated rat hepatocytes, mitochondria, and microsomes.

Yamano T, Morita S.

Osaka City Institute of Public Health and Environmental Sciences, Japan.

Twenty-seven pesticides, with which people are concerned, especially as residues in food, were examined in vitro for their effects on hepatocytes, mitochondria, and microsomes isolated from male rats. Nineteen pesticides returned non-protein sulfhydryl (NPSH) contents in hepatocytes to less than 80% of control at concentrations from 10(-3) to 10(-5) M after 90 min incubation. Among them, only dichlofluanid was reactive with glutathione non-enzymatically. Lipid peroxidation in hepatocytes was stimulated by five pesticides at 10(-3) M, with edifenphos being the most potent peroxidant. Cell viability was considerably decreased by incubation with chlorobenzilate, edifenphos, dichlofluanid, and chinomethionat at 10(-3) M, and in these cases, depletion of cellular adenosine 5'-triphosphate (ATP) contents proceeded to cell death. With respect to isolated mitochondrial respiration, six pesticides inhibited state 3 and/or state 4 respiration rates at concentrations from 10(-3) to 10(-5) M, whereas three pesticides uncoupled state 4 respiration at 10(-3) M. With respect to isolated microsomal lipid peroxidation, seven pesticides, five of which were organophosphorus compounds, were peroxidative at concentrations from 10(-3) to 10(-5) M, whereas seven pesticides were antioxidative at concentrations from 10(-3) to 10(-7) M. Only three pesticides, aldicarb, maleic hydrazide, and chlormequat chloride had no effect on any parameters tested at 10(-3) M. Pesticides that affected isolated mitochondria or microsomes did not necessarily have any effect on isolated hepatocytes.

PMID: 8368870 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=8335886&dopt=Abstract

J Environ Sci Health B 1993 Aug;28(4):397-411

[The effect of commercial preparations of benlate, dithane M-45, copper sulfate and dichlofluanid on the fertility of Drosophila melanogaster meigen]

[Article in French]

Marchal-Segault D.

Laboratoire Reproduction, Developpement de l'Insecte, Universite de Paris Sud, Orsay, France.

Four day old Drosophila pairs were maintained on nutritive media surface treated with fungicide doses according to the standard level recommended by the manufacturers. The flies were treated for 1 to 6 weeks and the eggs laid in 3 hours were counted each week during and after treatment. The capacity of treated flies egg laying was determined on treated media and then on untreated one. For the benomyl preparation (Benlate) and the mancozebe preparation (Dithane M45), there was an overall reduction of the egg mass on treated media but not on untreated media. There appears to be an essential repulsive effect which perturbs egg laying and causes a retention of eggs. However, after 3 to 4 weeks the quantity of egg mass also diminished on untreated media. Once the treatment was terminated the capacity to lay eggs partially returned. The copper sulfate preparation (Bouillie bordelaise) also exhibited a repulsive effect as exhibited by a retention of a certain number of eggs, but there was a more direct and fast effect on fecundity. Effect was more brutal with the dichlofluanide preparation (Euparene), and rapidly irreversible: the egg masses were very reduced after only one week of treatment on both treated and untreated media, and after termination of treatment there was an incomplete and temporary recuperation of the capacity to lay eggs. The results presented here are in agreement with those obtained previously concerning longevity. At the doses recommended for agricultural treatments, Benlate and Dithane M45 showed low toxicity for Drosophila adults in comparison with Bouillie bordelaise and Euparene which revealed a high toxicity in agreement with the fecundity and longevity data.

PMID: 8335886 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1803443&dopt=Abstract

Rocz Panstw Zakl Hig 1991;42(2):163-6

[Study of penetration to surface waters of pesticides used for protection of greenhouse plants]

[Article in Polish]

Sadlo S, Rupar J.

Terenowej Stacji Doswiadczalnej w Rzeszowie Instytutu Ochrony Roslin w Poznaniu.

Study was made of waste waters from two of the seven state horticultural farms producing vegetables and flowers, located in South-Eastern Poland, samples were taken from collectors carrying waste waters from the greenhouse culture surface, from a ditch and from the Wislok River where these waste waters are carried. Pesticides were extracted with dichloromethane or petroleum ether. Extracts were evaporated to dryness, whereupon the residues were dissolved in 5 ml of acetone or petroleum ether, and were analysed by gas chromotography (series 104 Pye Unicam gas chromotograph fitted with ECD and TID detectors). The following pesticides were found to penetrate into waste waters: methylpyrimiphos, methidathion, fenitrothion diazinon, methoxychlor, endosulfan, iprodione, vinclozoline, captan, carbendazim (MBC), dichlofluanid. These pesticides were present also in water samples collected from aditch into which waste waters from one of the investigated state farms are carried. There were no pesticides in samples of the Wislok River waters.

PMID: 1803443 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2939900&dopt=Abstract

Biomed Environ Mass Spectrom 1986 Apr;13(4):181-6

Chemical ionization mass spectrometry of dichlofluanid and its major metabolite.

Cairns T, Siegmund EG.

Gas chromatographic/mass spectrometric techniques using chemical ionization have been employed to characterize the fungicide dichlofluanid and its major metabolite. The results have indicated some unusual fragmentation pathways for perhalogenmethylmercapto compounds. Use of deuterated ammonia as reagent gas has permitted a comparative assessment of protonation and exchangeable hydrogens within the major fragment ion structures. Resultant structural information has been employed to confirm residue findings in strawberries at the low part-per-million level.

PMID: 2939900 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7250372&dopt=Abstract

FEBS Lett 1981 May 5;127(1):37-9

No Abstract available

Herbicides and fungicides stimulate Ca2+ efflux from rat liver mitochondria.

Hertel C, Quader H, Robinson DG, Roos I, Carafoli E, Marme D.

PMID: 7250372 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7245919&dopt=Abstract

Z Lebensm Unters Forsch 1981 May;172(5):368-72

The stability of dichlofluanid and vinclozolin and their influence on the quality of strawberries.

Davidek J, Hajslova J, Svobodova Z.

The content of dichlofluanid and vinclozolin found on strawberries treated with Euoparen and/or Ronilan, respectively, did not exceed the residue tolerance. Further decrease of the amount of these fungicides occurred during heatsterilisation of the fruit and storage of the products. The rate of decomposition of dichlofluanid and/or vincolozolin in model solutions (pH 3.0-6.0) followed pseudo-first-order kinetics. The taste and flavour of untreated fruit was preferred to those of strawberries treated with fungicides. There were differences in the content of reducing sugars, volatile fatty acids and titrable acidity in individual samples. Gas-chromatographic profiles of volatile substances isolated from treated and untreated berries also differed.

PMID: 7245919 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=737348&dopt=Abstract

Bull Environ Contam Toxicol 1978 Nov;20(5):702-6

Persistence of fungicide Euparen on strawberry and/or in some canned products of strawberry.

Seifert J, Blattny C, Henzlerova H, Davidek J.

There was studied the persistence of Euparen (dichlofluanid) on strawberry and in some canned products of strawberry, respectively. The rate of decrease of dichlofluanid residues on the leaves of strawberry is proceeding according to the first-order reaction kinetics in the initial 21 days. The content of dichlofluanid residues on strawberry treated twice with fungicide varies from 0.5 to 1.0 ppm, for strawberry sprayed three times from 1.0 to 2.0 ppm, respectively. The significant decay of dichlofluanid residues occurs during the technological procedures applied. The sensoric analysis of strawberry has proved the negative influence of the third spray of fungicide in the initial days. No significance differences between strawberry treated with fungicide and control has been found in flavor and taste of the canned products investigated.

PMID: 737348 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=806203&dopt=Abstract

Zentralbl Veterinarmed A 1975 Apr;22(3):256-9

No Abstract available

[Poisoning of a puma with the fungicide dichlofluanid]

[Article in German]

Kohout F.

PMID: 806203 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=6074707&dopt=Abstract

Chem Ind 1967 Aug 12;32:1359-60

No Abstract available

Estimation of dichlofluanid residues in strawberries.

Eades JF, Gardiner KD.

PMID: 6074707 [PubMed - indexed for MEDLINE]


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