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    FAO/PL:1969/M/17/1

    WHO/FOOD ADD./70.38

    1969 EVALUATIONS OF SOME PESTICIDE RESIDUES IN FOOD

    THE MONOGRAPHS

    Issued jointly by FAO and WHO

    The content of this document is the result of the deliberations of the
    Joint Meeting of the FAO Working Party of Experts and the WHO Expert
    Group on Pesticide Residues, which met in Rome, 8 - 15 December 1969.

    FOOD AND AGRICULTURE ORGANIZATION OF THE UNITED NATIONS

    WORLD HEALTH ORGANIZATION

    Rome, 1970

    DICHLOFLUANID

    IDENTITY

    Chemical name

    N,N-dimethyl-N'-phenyl-(N'-fluorodichloromethylthio)-sulphamide
    N'-dichlorofluoromethylthio-NN-dimethyl-N'-phenylsulphamide

    Synonyms

    Euparen (R), Bay 47 531

    Structural formula

    CHEMICAL STRUCTURE 

    Other relevant chemical properties

    The pure material is a white powder with slight characteristic odour,
    m.p. 105.0-105.6°C; insoluble in water at 20°C, solubility in methanol
    1.5 g/100 ml and in xylene 7.0 g/100 ml. The purity of the technical
    material is at least 96 percent and the product contains
    N',N'-dimethyl-N-phenyl sulphamide (DMSA) not more than 1 percent and
    ionogenic chlorine max. 0.3 percent. The technical product is
    formulated as 50 percent wettable powder and 7.5 percent dust. The
    active ingredient decomposes in alkaline media and in the presence of
    polysulphides. It is light-sensitive, but the discoloration induced
    does not affect its biological activity.

    EVALUATION FOR ACCEPTABLE DAILY INTAKE

    BIOCHEMICAL ASPECTS

    No information is available on the rate of absorption and on the
    distribution of dichlofluanid in the animal body. Studies in rats
    indicate that the absorption is small. Within 72 hours, 45-92 Percent
    of the administered dose could be isolated from the fences. Most of
    the dichlofluanid found was in an unchanged form; approximately 12
    percent was isolated as N,N-dimethyl-N'-phenylsulphamide. After oral
    administration of dichlofluanid the unchanged form of the compound van
    not detectable in the serum or urine; however when either
    dichlofluanid or its metabolite dimethylphenylsulphamide was
    administered orally, four metabolites could be isolated from the
    urine. The structures of those compounds have now been determined and
    are given below:

    CHEMICAL STRUCTURE 

    All the metabolites are excreted in the free-form and the metabolites
    III and IV are also excreted as glucuronides. Metabolites I and II can
    also be found in serum. The metabolites found in urine and serum after
    oral administration of dichlofluanid are the same as those found after
    oral administration of dimethylphenylsulphamide. From these studies it
    is evident that dichlofluanid is absorbed only very slightly, if at
    all, from the gastrointestines tract (Eben and Kimmerle, 1968, Bayer,
    1969).

    In the studies on the metabolism of dichlofluanid there is no
    information on the fate of the dichlorofluoromethylthio-portion of the
    molecule, and it is not known if the fluorine atom appears ultimately
    as fluoride ion. However, alkaline hydrolysis of dichlofluanid in
    methanol solution is reported to yield N
    N-dimethyl-N'-phenylsulphamide and fluorodichloromethanethiol
    (Cl2FCSH) which is susceptible to oxidation. No information is given
    on the nature of the oxidation products (Nangniot et al., 1967).

    Special studies on reproduction

    Rat

    Groups of rats, each comprising 10 male and 20 female animals,
    received dietary levels of 0, 150, 500, 1500 and 4500 ppm of
    dichlofluanid for a period extending over three generations. Two
    litters per generation wore followed and there were no deformities at
    any dose-level. The groups fed 150, 500 and 1500 ppm displayed no
    abnormal effects with respect to fertility, litter-size and percentage
    survival to weaning. In the group given 4500 ppm there was no
    difference from the control group in the F1b generation, but in the
    F2b and succeeding generations to F3b, the body-weights of the
    young animals were significantly lower both at birth and during
    weaning. In the 4500 ppm group the lactation index was also slightly
    reduced after one of the six matings (Löser, 1969).

    Special studies on the metabolite, N,N-dimethyl-N'-phenylsulphamide

    Rat

    Groups of 30 rats (15 of each sex) were fed 0, 1000, 3000, and 10,000
    ppm of dimethylphenylsulphamide in their diets for four months.
    Mortality, food consumption, growth, haematology, urinalysis, gross
    and microscopic pathology (10 animals from each group) were closely
    comparable in the experimental and the control groups. Also the final
    average body and organ-weights were comparable in the different
    groups, except in the 10,000 ppm group where the female rate displayed
    a decrease in the adrenal weight; and in both sexes an increase in the
    liver-weight was found. Although no histopathological changes in the
    liver and the kidney of these rats were reported. such might be
    camouflaged by the histological changes due to infections (Lorke,
    1965).

    Acute toxicity
                                                                                
                                      LD50 mg/kg
        Animal             Route      body-weight         References
                                                                            

    Mouse         (F)      i.p.       7.8           DuBois and Raymund, 1963

    Mouse         (M)      i.p.       6.0           DuBois and Raymund, 1963

    Chicken                oral       >1000         DuBois, 1963

    Rat           (M)      i.p.       15            DuBois and Raymund, 1963

    Rat           (F)      i.p.       15            Bayer, 1962
                                                    DuBois and Raymund, 1963

    Rat           (M)      oral       500-1000      DuBois and Raymund, 1963

    Rat           (F)      oral       525           Bayer, 1962
                                                    DuBois and Raymund, 1963

    Guinea-pig    (M)      i.p.       35            DuBois and Raymund, 1963

    Guinea-pig    (M)      oral       250           DuBois and Raymund, 1963
                                                                            
    
    The symptoms of poisoning were non-typical and consisted mainly in a
    decrease in activity which began several hours after administration of
    the compound. With doses around the LD50, death occurred in one to
    four days (DuBois and Raymund, 1963)

    Short-term studies

    Dog

    Groups of four dogs (two of each sex) were fed 0, 500, 1500, and 4500
    ppm of dichlofluanid in their diets for four months. Behaviour, food
    consumption, body-weight changes, mortality, function tests of the
    liver and kidney urinalysis, gross pathology and final average
    body-weights and average organ-weights were closely comparable in the
    500 ppm and the control group. The same was the case with the male
    dogs of the 1500 ppm group while in the females changes in
    liver-function tests and decrease in body-weight pointed at an
    impaired liver-function. Three of the four dogs fed 4500 ppm of
    dichlofluanid died. Before death these dogs and also the surviving
    animal displayed signs of impaired liver and kidney function (Lorke
    and Löser, 1966).

    Rat

    Groups of 30 rats (15 of each sex) were fed 0, 30, 100, 300, 1000,
    3000, and 10,000 ppm of dichlofluanid in their diets for four months.
    Food consumption, growth, haematology, urinalysis, mortality, gross
    and microscopic pathology were closely comparable in the 30 to 3000
    ppm experimental groups and the control groups. The same was the case
    with final average body and organ-weights except in the 3000 ppm group
    where the male rats displayed reduction of heart-weights and the
    female rate an increase in liver-weights. In the rats fed 10,000 ppm
    there was a deterioration of general condition, decreased food intake,
    smaller weight gains, and higher mortality than the control group. The
    male rats showed a decrease in heart weights, while in both cases
    there was a decrease in the weight of adrenal glands and an increase
    in liver-weights. Histopathological changes were found in the liver
    (vacuolization, inflation in size and shrunken nuclei of some cells),
    kidneys (increased protein precipitation in the proximal tubuli) and
    the spleen (reduction of the lymphatic tissue) (Bayer, 1964).

    Long-term studies

    Rat

    Groups of 80 rats (40 of each sex) were fed 0 (two groups), 150, 500,
    1500 and 4500 ppm of dichlofluanid in their diets for two years.
    Behaviour, food consumption and mortality of the test groups did not
    differ from the parameters of the control groups. The same was the
    case with haematology (at 4 and 24 months) and liver function and
    urine examination (at 24 months). Gross pathology of animals which
    died during the experiment, and of sacrificed test rats at the end of
    the study, did not reveal any changes that might be caused by
    dichlofluanid, but no histological examination of the organs is
    recorded. Female rats in the 4500 ppm group showed decreased weight
    gain and relative kidney-weights, while both sexes showed elevated
    relative liver-weights, but normal enzyme function tests (Löser,
    1968).

    COMMENT

    No information is available on the absorption or metabolism of
    dichlofluanid in man or in animal species other than the rat. In
    particular there is no information reported on the metabolism of the
    dichlorofluoromethylthio-moiety. It is known that chemical hydrolysis
    gives dichlorofluoromethanethiol and this observation is of some
    concern when related to possible metabolic breakdown of dichlofluanid.
    It cannot be assumed that the metabolism would ultimately result in
    the formation of fluoride ions as the carbon-fluorine bond is known to
    be highly resistant to cleavage, and thus there is a possibility that
    other organofluorine compounds could result from the metabolism. This
    possibility needs elucidation.

    The 500 ppm level of dichlofluanid in the four-month study in dogs
    seems to have no toxicological effects but no histological studies
    were reported. In the four-month feeding study in the rat, the 1000
    ppm dose level appeared to be without toxic effect. The long-term
    study in rats was also not considered adequate because there was no
    histological information provided. There are also no data from
    observations in man nor from a one to two year study in a non-rodent
    mammalian species.

    For these reasons no acceptable daily intake could be established.

    RESIDUES IN FOOD AND THEIR EVALUATION

    USE PATTERN

    Pre-harvest treatments

    Dichlofluanid is a fungicide with a broad spectrum of activity. It is
    chiefly used for controlling scab of apple and pear, Botrytis of
    strawberry and grape vine, Peronospora of grape vine and hop. Further
    it is used or recommended for testing on tomato, cucumber, lettuce,
    onion, cherry, plum, peach, currants, citrus fruits, and pecans.

    It has good plant tolerance at the recommended concentrations,
    although, according to location and variety, slight injuries may be
    caused on stone fruits and on ornamentals (Anon., 1965). Some
    interference in the act and development of fruit on some varieties of
    strawberries has also been reported (Gourley, 1968). Dichlofluanid is
    harmless to bees.

    Safety intervals have been laid down in several European countries,
    which differ according to the recommendations, crops and tolerances
    where these are established.

    Post-harvest treatments

    No post-harvest treatments are recommended.

    Other uses

    Dichlofluanid is used for the treatment of ornamentals, especially for
    the control of fungal diseases on roses. Dichlofluanid can be used for
    control of powdery mildew without adversely affecting the quality of
    tobacco. Dichlofluanid has a good side-effect against spider mites.

    RESIDUES RESULTING FROM SUPERVISED TRIALS

    The following tables give the residues of dichlofluanid and its
    metabolite DMSA found in the listed crops after application at the
    recommended concentrations. The analyses were carried out by
    Farbenfabriken Bayer AG, Germany, The State Institute of Agricultural
    Chemistry, Finland, and various institutes (Anon., 1967, 1968, 1969).
    The residues on grapes show large differences which may be dependent
    upon several factors ouch as plot size, nature of grape development in
    the different wine-growing districts, spraying technique and spraying
    machine (Vogeler and Goeldner, 1967; Hurter at al., 1967). Also on
    other crops the variation of residues greatly interferes with the
    evaluation of data.

        TABLE I
                                                                                        

    Residue data from field trials

    Crop                Number of      Pre-harvest         Residue at harvest (ppm)
                        treatments       interval
                                          (days)      Dichlofluanid           DMSA
                                                                                        

    Apples              1 - 12         10 - 14        0.2 - 3.2            not determined

    Strawberries        1 - 4          11 - 14        n.d.- 3.6            0.25 - 3.1

    Raspberries         3 - 4          7              5.9 - 13.8           0.65 - 6.4
                                       13 - 14        2.3 - 10.5           0.45 - 4.0

    Fresh currants      3 - 7          14             0.9 - 2.2            0.8 - 1.0

    Grapes              2 - 6          40 - 50        0.7 - 10.9           0.25 - 4.4

    Lettuce             5 - 6          14             n.d.- 0.3            0.8 - 2.5

    Tomatoes            1 - 3          5 - 7          0.1 - 0.2            0.1 - 0.9
                                                                                        

    n.d. = not detected
    
    FATE OF RESIDUES

    General comments

    Dichlofluanid is degraded to N', N'-dimethyl-N-phenyl sulphamide
    (DMSA) under alkaline conditions in vitro, on the plant, and partly in
    the gastrointestinal tract. (Also see entry under 'BIOCHEMICAL
    ASPECTS' above). Amounts of residues on the plants are given Table I.
    The metabolite DMSA is less toxic than dichlofluanid and is
    fungicidally ineffective.

    In animals

    Dichlofluanid is either not resorbed at all from the gastrointestinal
    tract or, if so, then only in a very slight extent. Dichlofluanid,
    after being fed to rats, is degraded to DMSA.

    In plants

    Dimethylaminosulphanilide occurs as a metabolite of dichlofluanid on
    all plants (Vogeler and Niessen, 1967).

    The residue analyses show that the metabolite already forms on the day
    dichlofluanid to applied. The proportion of metabolite in the total
    residue varies according to the nature of the plant material. It does
    not exceed the proportion of dichlofluanid, except in the case of
    processed fruits and sometimes on strawberries. The "half-life" of
    DMSA on apples is approximately 30 days; this value was determined in
    an experiment in which formulated DMSA was sprayed (Vogeler, 1965).

    The residue figures for dichlofluanid and its degradation product
    combined are only slightly higher than the figures of dichlofluanid.
    There is thus no evidence of buildup of the degradation product.
    Dichlofluanid is relatively persistent, having a "half-life" of about
    one week on strawberries. Consequently, the establishment of a
    withholding period short enough to permit the use of dichlofluanid on
    strawberries throughout the harvest period seems so far questionable
    (Brewerton and Gibbs, 1968).

    Rainfalls may cause considerable falls in the residues of
    dichlofluanid.

    In soil

    Data on dichlofluanid residues in soil are not available.

    In storage and processing

    Nothing is known about the degradation of dichlofluanid on fruit in
    storage. There are few figures available on effects of washing and
    peeling of fruit on the residue levels (Table II). No final
    conclusions can be made although the results indicate that variable

    amounts of residues could be washed off and a substantial part of
    residue was removed by peeling.

    There was a decrease of the amount of residues in the canning process
    of strawberries (Kavanagh at al., 1968). Following applications at the
    recommended dosage, residues on deep-frozen strawberries amounted up
    to 1.5 ppm; on the other hand, canned fruits and juice originating
    from the same sample contained a maximum of about 0.1 ppm. Following
    application at twice the recommended dosage, canned strawberries
    contained up to 0.88 ppm. The reduction of residues in the canning
    process is presumably canned by washing with water. According to
    Kavanagh et al., DMSA was not detected in any sample of frozen or
    canned fruit.

    It has been reported that the dichlofluanid treatment of strawberries
    would tend to increase the sweetness and acidity of the berries (Kirby
    and Arthey, 1966).

    Strawberry jam made from treated fruits contained dichlofluanid
    residues of less than 0.1 ppm and DMSA residues of between 0.15 and
    0.4 ppm. The content of residues in the treated strawberries amounted
    to 0.4 to 1.15 ppm dichlofluanid and 0.8 to 0.85 ppm DMSA (Maier-Bode,
    1966).

    To investigate the residues in wine field-treated grapes as well as
    marc, must, and wine yielded from them were analysed (see also Vogeler
    and Goeldner, 1967) (Table III). The analyses showed that these wines
    contained no residue of dichlofluanid and only small residues of DMSA.
    A further 20 analyses of different wines made from treated grapes
    showed no residues of dichlofluanid and the amounts of DMSA residues
    found ranged from "not detectable" to 2.95 ppm. In these analyses the
    amount of the residue on the grapes was unknown. In the course of wine
    processing, the residues are removed by the pressing process and
    pre-clarification (desliming) of the must. In marc very high residues
    are found.

        TABLE II
                                                                           

    Effect of washing and peeling on residue levels

                  Pre-harvest   Residue at    Residue after    Residue after
                   interval       harvest        washing         peeling
    Crop            (days)         (ppm)          (ppm)           (ppm)
                                                                           
    Apple             14            2.0            1.3             0.4
                      14            3.3            4.0             1.5
    Strawberry        14            0.07           0.03             -
                      19            0.5            0.15             -
                      19            0.6            0.20             -
                                                                           
    
        TABLE III

    Dichlofluanid and DMSA residues in grapes and must, marc, and wine made
    from treated grapes

                                                                              
                                                           Residue
                                 Pre-harvest                (ppm)
                    Number of    interval
    Crop            treatments   (days)        Dichlofluanid     DMSA
                                                                              

    Grapes          2 - 9        21 - 95       0.4  - 5.4        0.25 - 1.35

    Must, not
    clarified                                  n.d. - 2.0        0.3  - 0.95

    Must,
    clarified                                  n.d. - 0.05       0.25 - 0.4

    Marc                                       0.4  - 53.0       8.9  - 47.0

    Smashed                                    1.2  -  5.0       not determined

    Peels                                      0.6  - 11.1       not determined

    Wine                                       n.d. -  3.9       n.d. - 2.95
                                                                              

    n.d. = not detected
    
    METHODS OF RESIDUE ANALYSIS

    The most important method for determining residues of dichlofluanid is
    gas chromatography using an electron capture detector. This method may
    be used for analysing apples, strawberries, raspberries, currants,
    lettuce, tomatoes, wins and grapes (Vogeler and Niessen, 1967).
    Methods based on the same principle have been described for analysis
    of strawberries (Eades and Gardiner, 1967) and grapes (Hurter et al.,
    1966).

    Dichlofluanid may also be determined by polarography (Nangniot at al.,
    1967) and by colorimetry (Vogeler and Niessen, 1967). The colorimetric
    method is based on saponification of the parent compound to the
    metabolite DMSA and determination of aniline by diazotization and
    coupling with N-(1-naphtyl)-ethylene-diamine. By this method, the sum
    of parent compound and metabolite is obtained so that the metabolite
    is determined alone in a second analytical procedure in which alkaline
    saponification of the parent compound is omitted.

    The parent compound and the metabolite DMSA can be determined in one
    analytical procedure by gas chromatography and colorimetry after
    column-chromatographic separation (Vogeler and Niessen, 1967). The
    sensitivity of the colorimetric method is approximately 0.1 ppm and
    that of the gas chromatographic method is 0.1 ppm or less depending
    upon the response of the detector.

    NATIONAL TOLERANCES AND WITHHOLDING PERIODS
                                                                                                
                                                                             Saf. Int./
    Country                  Crop                           Tol./ppm            Days
                                                                                            

    Austria          General                                                     14
                     General                                15.0 proposed

    Belgium          General                                                     14
                     Fruits and vegetables                  5.0
                     except potatoes

    Denmark          General                                                     14

    Finland          General                                                     14

    France           Grapes, strawberries                                         7
                     "Kupfer-Euparen (6341)" Grapes                               7

    Germany
    (Fed.Rep.)       Pome fruit                                                   7
                     Cane and bush fruit                                          7*
                     Strawberries                           2.0 + 2.0 DMSA       14
                     Tomatoes                               1.0 + 1.0 DMSA        3*
                     Apples and pears                       0.5 + 0.5 DMSA

    Italy            WP:  General                                                20
                     Grapes                                                      40
                     Strawberries                                                20
                     6012 (40% + 10% Cu) General                                 15
                     "Ramato blu (15% + 30% Cu)" General                          7

    Netherlands      General                                5.0
                     Strawberries, raspberries,
                     blackberries                                                 7
                     Currants                                                    21
                     Strawberries grown under glass                              14

    Norway           General                                                      7

    Poland           Fruits, vegetables, field crops                             14
                     Grapes                                                      42

    (cont'd)
                                                                                            
                                                                             Saf. Int./
    Country                  Crop                           Tol./ppm            Days
                                                                                            

    Sweden           General                                                      7

    Switzerland      General                                                     21
                     Grapes                                 1.0
                     Strawberries                           7.0

    United Kingdom   Strawberries, raspberries                                   14

                     Blackberries, blackcurrants,
                     gooseberries, loganberries,
                     onions, cauliflower (grown under
                     glass), lettuce (grown under
                     glass), lettuce (field grown)                               21

    Yugoslavia       Strawberries                           2.0 + 2.0 DMSA       14
                     Grapes                                                      30
                                                                                            

    * subject to official approval
    
    APPRAISAL

    Dichlofluanid is a fungicide with a broad spectrum of activity. It is
    chiefly used for controlling scab of apple and pear, Botrytis of
    strawberry and grape vine, Peronospora of grape vine and hop, and
    mildew of roses. Further, it is used or recommended for testing on
    tomato, cucumber, lettuce, onion, cherry, plump peach, currants,
    citrus fruits and pecans. Concentration of the sprays is recommended
    to 0.075-0.12 percent active ingredient. Dichlofluanid has a good
    side-effect against spider mites. Although there is a good plant
    tolerance to dichlofluanid, slight injuries may be caused, according
    to location and variety, on some stone fruits. It is harmless to bees.
    Dichlofluanid is used in many European countries and the safety
    intervals from the last treatment to the harvest vary from three to
    forty days. The national tolerances applied vary from 1 to 7 ppm for
    dichlofluanid alone or for dichlofluanid plus its metabolite DMSA. It
    is formulated as 50 percent wettable powder and 7.5 percent dust.

    The residue data available to the meeting were obtained from
    supervised field trials in Germany, England and Finland. Initial
    residues of dichlofluanid had usually degraded by one half within a
    week; on grapes more persistent residues were found. By washing,
    peeling and processing, residues are partly removed.

    Dichlofluanid is degraded to N',N'-dimethyl-N-phenyl sulphamide (DMSA)
    under alkaline conditions in vitro, on all plants, and in the

    gastrointestinal tract. In addition to DMSA, in urine three other
    metabolites of dichlofluanid are detected and identified. Residue data
    on DMSA are available and its "half-life" on apples is determined (30
    days). In processed strawberries both dichlofluanid and DMSA are
    found. Wines produced from treated grapes are found to contain both
    dichlofluanid and DMSA. The occurrence of DMSA seems to be, however,
    more relevant than that of the parent compound. In plants or plant
    products DMSA is the only degradation product of dichlofluanid so far
    identified.

    The documentation on dichlofluanid includes methods of residue
    analysis based on GLC, polarography and colorimetry. Both the parent
    compound and DMSA can be determined. A sensitivity of 0.1 ppm in plant
    material can be reached.

    RECOMMENDATIONS FOR TOLERANCES, TEMPORARY TOLERANCES
    OR PRACTICAL RESIDUE LIMITS

    As no acceptable daily intake was established, no tolerances were
    recommended.

    FURTHER WORK OR INFORMATION

    REQUIRED (before an acceptable daily intake or tolerances can
    be established)

    1. Further information on the absorption and metabolism of the
       compound particularly with regard to the fate of the
       fluorine-containing portion of the molecule.

    2. A long-term feeding study in the rat including a histological
       examination of all major organs.

    3. A 1-2 year feeding study in a non-rodent mammalian species.

    4. Information on the composition of the technical dichlofluanid,
       including the impurities.

    5. More detailed information on the nature and magnitude of terminal
       residues in plants including data on the fluorine-containing moiety 
       of the molecule.

    6. Information about possible degradation mechanism of the molecule by
       the action of sulfhydryl compounds in vitro and in vivo.

    7. Data on the required rates and frequencies of application,
       pre-harvest intervals, and the resultant residues from different
       countries, especially on those crops which have shown inconsistency 
       of residue data. Data on degradation products of dichlofluanid, if
       important in magnitude or toxicologically, should be included.

    8. Data on residue levels in raw agricultural products moving in
       commerce.

    9. Qualitative and quantitative data on fate of residues in washing,
       blanching and storing and thermal processing of treated crops.

    10. Data concerning the possible occurrence of the parent compound in
        wines produced from treated grapes.

    DESIRABLE

    1. Metabolism in animal species, other than the rat.

    2. Metabolic studies and other observations in man.

    3. Information on the fate of the compound in soil.

    4. Evaluation of the analytical methods by collaborative studies for
       regulatory purposes.

    REFERENCES

    Anon. (1965) (R)Euparen (Bay 47531). Pflanzenschutz. Farbenfabriken
    Bayer AG. Technical Information Sheet

    Anon. (1967) Investigations on pesticide residues. Publications of the
    State Institute of Agricultural Chemistry. Tikkurila, Finland, No.1.

    Anon. (1968) Ibid. No.2

    Anon. (1969) Ibid. No.4

    Bayer (1962) Product Kü 13-032-C. Unpub. Rept. prepared and submitted
    by the Institute of  Toxicology, Farbenfabriken Bayer AG.

    Bayer (1964) Report of 4-months feeding study on rats with active
    ingredient 47531. Unpub. Rept. prepared and submitted by the Institute
    of Toxicology, Farbenfabriken Bayer AG.

    Bayer (1969) Dichlofluanid. Unpub. Summary Rept. prepared and
    submitted by Farbenfabriken Bayer AG.

    Brewerton, H.V. and Gibbs, M.M. (1968) Dichlofluanid ("Euparen")
    Residues on Strawberries. New Zealand J. Agr. Res. 11:784-88

    DuBois, K.P. (1963) The acute toxicity of Bayer 47531 to chickens.
    University of Chicago. Unpub. Rept. submitted by Farbenfabriken Bayer
    AG.

    DuBois, K.P. and Raymund, A.B. (1963) The acute toxicity of Bayer
    47531 to mammals. University of Chicago. Unpub. Rept. submitted by
    Farbenfabriken Bayer A.G.

    Eades, J.F. and Gardiner, K.D. (1967) Estimation of Dichlofluanid
    Residues in Strawberries. Chemistry and Industry 32:1539-60

    Eben, A. and Kimmerle, G. (1968) Studies on the metabolism of Bayer
    47531. Unpub. Rept. prepared and submitted by the Institute of
    Toxicology, Farbenfabriken Bayer AG.

    Gourley, C.O. (1968) Fungicidal control of Botrytis cinerea on four
    strawberry varieties. Can. J. Plant Sci. 48:267-72

    Hurter, J., Mayer, K. and Zürrer, A. (1966) Gärhemmung durch
    Fungizidrückstände Schweizerische Z. Obst- und Weinbau 102:592-7

    Hurter, J., Lauber, H.P., Mayer, K., Schüepp, H. and Bolay, A. (1967) 
    Rückstandsmenge auf Weintrauben und Gärnerlauf nach Behandlung mit
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    See Also:
       Toxicological Abbreviations
       Dichlofluanid (WHO Pesticide Residues Series 4)
       Dichlofluanid (Pesticide residues in food: 1977 evaluations)
       Dichlofluanid (Pesticide residues in food: 1979 evaluations)
       Dichlofluanid (Pesticide residues in food: 1981 evaluations)
       Dichlofluanid (Pesticide residues in food: 1982 evaluations)
       Dichlofluanid (Pesticide residues in food: 1983 evaluations)