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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)
Order from NTIS by: phone at 1-800-553-NTIS (U.S. customers);
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Springfield, VA, 22161, USA. |
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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