WHO/FOOD ADD./70.38



    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.



    Rome, 1970



    Chemical name

    2,4-dinitro-6-s-butylphenyl 3-methylcrotonate


    2-sec-butyl-4,6-dinitrophenyl 3-dimethylacrylate, Acricid(R),
    Morocide(R), Endosan(R), Ambox(R)

    Structural formula


    Other relevant chemical properties

    The technical material is claimed to contain 96 percent binapacryl;
    the composition of the remaining 4 percent has not been revealed. The
    vapour pressure of the pure product is 1 × 10-4 Torr at 60°C. The
    solubility in water is low, moderate (11 percent) in ethanol and
    kerosene, but exceeding 50 percent in heavy aromatic naphtha,
    isophorone, xylene and acetone.

    Binapacryl is stable under normal conditions but is decomposed slowly
    by U.V. radiation. It is readily hydrolyzed by strong acids or dilute
    alkalis; a small degree of hydrolysis will occur in water after
    prolonged contact.

    Formulated products include wettable powders containing 50 percent
    a.i. (formerly 25 percent a.i.), an emulsifiable concentrate (40
    percent a.i.), a 'Col' suspension (50 percent w/v a.i.), and dusts (3
    or 4 percent a.i.).



    Absorption, distribution and excretion

    When male and female dogs were fed daily oral doses of 1 or 10 mg/kg
    body-weight of binapacryl, the faeces were found to contain mainly the
    unchanged compound; but only small amounts of binapacryl itself were
    found in the urine, blood and organ tissues. Three dinitro-metabolites
    were found and the metabolic pathway shown in Figure 1 was proposed.
    There were no amine or conjugated metabolites found in the blood and
    urine in dogs. About 70 percent of the phenol, dinoseb (II), formed in
    the blood, was converted to the alcohol (III). This alcohol was
    detected in both blood and urine, whereas the acid (IV), formed from
    its oxidation, was only found in the urine (Chin and Stanovich, 1964).

    A similar indication of low absorption of unchanged binapacryl, as
    well as rapid biotransformation to dinoseb, before or after
    absorption, was found in guinea-pigs. In these studies, fasted
    guinea-pigs were given a single dose of either 400 mg/kg body-weight
    of binapacryl or 40 mg/kg of dinoseb by stomach tube. No binapacryl
    could be detected in the blood prior to death, but the concentration
    of dinoseb in the blood was within the same range in both groups,
    indicating that the toxic effect of binapacryl is due to its
    hydrolytic product, dinoseb (Bough et al., 1965).

    Rabbits given oral doses of 60 mg/kg body weight of binapacryl or 20
    mg/kg of dinoseb excreted five metabolites in the urine, one of which
    was 2-(2-butyl-)-4-nitro-6-aminophenol, present both in a free and in
    a glucuronide-conjugated form. In the urine of rats only traces of the
    amine and none of the conjugated form was found. In both species,
    metabolites resulting from side-chain oxidation, e.g.
    3-(2-hydroxy-3,5-dinitrophenyl)-butyric acid, were found (Ernst and
    Bär, 1964).

    Quantitative studies of the urinary excretion in rats and rabbits
    after a single administration of binapacryl was found to be 7 - 17
    percent of the applied dose within 48 hours. Even during the tenth day
    0.12 percent of the dose administered was detected in urine from rats
    (Ernst and Bär, 1964).


    Special studies on cataract formation


    Groups of 15 chickens were fed binapacryl, dinocap or
    2,4-dinitrophenol in the diet for 17 - 28 days. The incidence of lens
    opacities was investigated by gross autopsy on dead or killed birds.
    At dietary levels of 900 and 1800 ppm of binapacryl, of 1000 and 2000
    ppm of dinocap and 500, 1000 and 2000 ppm of dinitrophenol no


    opacities were found. At dose levels of 3500 ppm of binapacryl, 4000
    ppm of dinocap and 3000 ppm of dinitrophenol and at higher levels
    there was a distinct incidence of cataracts (Cervenka and Kay, 1963).

    Special studies on reproduction


    Groups of rats (8 males and 16 females) were fed 0, 1, and 50 ppm of
    binapacryl for three generations. The F0, F1b and F2b generations
    were used as parents. The reproductive performance as measured by the
    indices of mating, pregnancy, fertility, parturition and lactation,
    was not influenced by the feeding with binapacryl. Neither were the
    different parameters of the progeny e.g. litter size, number of
    stillbirths, viability, survival and weight of weanlings. No special
    teratological studies were carried out, but upon weaning of the F3b
    litters, gross and histological examination of several of the animals
    from all groups did not reveal any changes attributable to binapacryl
    (Kennedy and Calandra, 1965a, 1965b, 1965c).

    Special studies on the metabolite, dinoseb

    Comparative toxicity of dinoseb and binapacryl

    In acute toxicity and blood level studies on binapacryl and dinoseb in
    a variety of small animals covering a wide range of doses, binapacryl
    was found to be considerably less toxic than dinoseb whether the
    compounds were administered orally (mouse, rat, guinea-pig and
    chicken) or percutaneously (guinea-pig and rabbit) (Bough et al.,

    The table shown under the heading "Acute toxicity" compares the LD50
    values for binapacryl and dinoseb in several species.

    Short-term studies

    Groups of male rats, comprising 30, 20, 20, 20 and 10 in number, were
    fed 0, 50, 100, 200 and 500 ppm, respectively, of dinoseb in their
    diet for up to six months. Of the 10 rate fed 500 ppm there was rapid
    weight loss and 4 died within two weeks. The survivors were sacrificed
    after three weeks and showed marked emaciation and, upon histological
    examination, slight degenerative changes in the kidney and cloudy
    swellings in the liver cells were found. In the groups fed 200 ppm or
    less, growth, mortality, haematology, bone-marrow count and blood-urea
    nitrogen determination at the end of the six month period, as well as
    average organ weights and histopathology were comparable with the
    controls, except for a slight decrease in growth rate and increase in
    liver weight in the group fed 200 ppm (Spencer et al., 1948).

    Acute toxicity

    Most of the studies on the acute toxicity of binapacryl are of a
    rather preliminary nature, but indicate the range of tissues within
    which the LD50 might be found. The following table also compares the
    values with those found for the metabolite, dinoseb:

                                     mg/kg body-weight

    Animal                Route    Binapacryl     Dinoseb    Reference

    Mouse (M)             oral     1600-3200      20-40      Bough et al., 1965

    Rat (M)               oral     150-225        25-40      Bough et al., 1965

    Rat                   oral     150-225        50         Edson et al., 1966

    Rat (mixed)           oral     220-350                   Hoechst, 1964

    Rat (mixed)           oral                    38         Spencer et al., 1948

    Rat                   dermal                  80-200     Edson et al., 1966

    Guinea-pig (F)        oral     200-400        20-40      Bough et al., 1965

    Guinea-pig (mixed)    dermal                  150-200    Spencer et al., 1948

    Rabbit (mixed)        oral     640                       Hoechst, 1964

    Rabbit                dermal   1350                      Edson et al., 1966

    Dog                   oral     450-640                   Hoechst, 1964

    Chicken (M)           oral     800            40-800     Bough et al., 1965
    Short-term studies


    Groups of dogs (three males and three females) were given 0, 0.25,
    1.25, 2.5, 5, and 25 mg/kg body-weight of binapacryl orally in
    gelatine capsules daily for two years. In the groups given 5 mg/kg and
    below mortality, food, consumption, body-weight, behaviour,
    haematology, blood biochemistry, urinalysis, liver function tests,
    organ-weight, organ to body-weight ratios, gross and microscopic
    pathology were comparable to the controls. The groups given 1.25, 2.5,
    and 5 mg/kg displayed a transient paresis of the hindquarters lasting

    5-10 hours after dosing. In the group given 25 mg/kg, depression and
    continuous paresis of the hindquarters wore observed, and all the dogs
    in this group died within six months (Baran at al., 1966).


    Groups of rats (10 males and 10 females) were fed 0, 25, 50, 100, and
    200 ppm of binapacryl in their diet for 90 days. Mortality, general
    condition, haematology, urinalysis, average organ-weight, gross and
    microscopic pathology were comparable in the experimental and the
    control groups. A slight decrease in weight gain occurred in the
    groups fed 100 and 200 ppm. The experiments were part of a two-year
    study (Hoechst, 1962).

    In a 64-week study, from which no detailed information is available,
    groups of rats (30 males and 30 females) were fed 0, 25, 100, and 500
    ppm of binapacryl in the diet. Of the parameters tested only a
    depression of body-weight was noted in the 100 and 500 ppm groups
    (Industrial Bio-Test Laboratories Inc., 1964).

    Long-term studies


    Groups of rats (30 males and 30 females) were fed 0, 25, 50, 100, and
    200 ppm of binapacryl in the diet for two years. After 90 days, 10
    males and 10 females were withdrawn from the experiment and evaluated
    separately (see "Short-term studies"). After one year of feeding
    approximately half of the remaining rats in the groups were subjected
    to interim sacrifice. Although a number of rats succumbed to
    intercurrent disease (pneumonia) during the two-year study, no effect
    on morbidity or mortality due to binapacryl was found. Food
    consumption, body-weights, haematology, urinalysis, average
    organ-weights, gross and microscopic pathology (including tumour
    incidence) were comparable in the experimental and control groups
    (Hoechst, 1962).


    Although the metabolism of binapacryl has been studied in several
    species, more studies on the absorption and excretion of the compound
    would be desirable. The short and long-term feeding study and the
    three-generation reproduction study in the rat as well as the two-year
    feeding study in the dogs are considered adequate. The observation of
    cataracts in chickens fed high-dose levels is of come concern. The
    two-year dog study is used as a basis for establishing an acceptable
    daily intake.


    Level causing no toxicological effect

    Rat: 200 ppm in the diets equivalent to 10 mg/kg body-weight/day

    Dog: 0.25 mg/kg body-weight/day


    0-0.0025 mg/kg body-weight



    Pre-harvest treatments

    Binapacryl is an acaricide of value for control of tetranychid mites
    on certain fruits, mainly apple, and vegetables. It is also used to
    control powdery mildew on apple. There is no evidence of systemic

    In England, in 1967, about 5,000 hectares of apples, mainly dessert,
    were sprayed at the recommended rate, 4 lb of the 25 percent W.P.
    then available per acre (1.16 kg a.i. per he), on average six or seven
    times at two-week intervals. In the U.S.A., binapacryl is registered
    for use on top fruit at 4 oz a.i. per 100 gal. (25 g per 100 litres),
    using not more than 4 lb of the 50 percent W.P. per acre (2.3 kg a.i.
    per ha). In West Germany, the recommended two-week rate is 0.1 percent
    of the 50 percent W.P. at 2,000 litres per ha (1 kg a.i. per ha), the
    current recommendation In the U.K. being 1.16 kg a.i. per ha.

    Post-harvest treatments

    A 4 percent dust is registered in the U.S.A. for use at 50 lb per acre
    (2.3 kg a.i. per ha) on cropping trees.


    Residues at intervals up to harvest have been reported (Buxton, 1962,
    1963; Emmel, 1960; Maier-Bode, 1967, unpublished; Maier-Bode, 1968;
    Stanovich, 1963; Versier, 1965). They are summarized in the following

                                  Rate            Interval         Residues*
    Crop                Year      a.i.            (days)           (ppm)
    Apples                        1.25 kg/ha        24              0.1-0.2
                                  0.05%              0              1.4
                                                     7              0.15
                                  2.5 kg/ha          0              1.4
                                                     7              0.35
                                                    14              0.25
                                  2.0 kg/ha          0              0.3
                                                     7              0.1
                                                    14              0.02

                                  Rate            Interval         Residues*
    Crop                Year      a.i.            (days)           (ppm)
    Apples                        2.0 kg/ha          0              1.1
    (cont'd)                                         7              0.6
                                                    14             <0.02
                                  1.5 kg/ha         14              0.5-0.64    (<0.02)
                                  1.5 kg/ha          0              1.62        (<0.02)
                                                     7              1.50-1.54
                                                    14              1.14-1.31
                                  1.5 kg/ha          0              2.0-2.2      (0.02)
                                                     7              0.91-1.06
                                                    14              0.80-0.87
                                                    22              0.37-0.45

                                  2.2 kg/ha          0              1.1-2.0      (0.02)
                                                     5              0.5-1.13
                                                    11              0.11-0.53
                                                    14              0.27-0.32

                                  0.125%             0              1.20         (0.10)
                                                     7              0.38         (0.05)
                                                    15              0.10         (0.03)

                                  0.03%     )        0              1.00-1.08    (0.04)
                                  1.7 kg/ha )        7              0.56-0.59    (0.02)
                                                    14              0.51-0.68    (0.02)
                                                    21              0.26-0.45    (0.02)

                                  0.06%              0              1.50         (0.02)
                                                     7              0.82-0.97
                                                    16              0.29-0.48
                                                    21              0.23-0.24

    Pears                         0.03%              0              3.0          (0.02)
                                                     5              1.87-2.3
                                                    11              0.98-1.09
                                                    19              0.34-0.35
                                  0.05%              6              3.3-3.7      (0.05)
                                                    14              0.8-1.1
                                                    27              0.15

                                  0.03%              0              0.5         (<0.02)
                                                    15              0.36
                                                    29              0.06

                                  0.03%              0              3.4          (0.03)
                                                     7              1.39-1.44    (0.04)
                                                    14              0.58-0.61    (0.03)
                                                    21              0.14        (<0.02)
                                  0.09%              0              6.9          (0.06)

    Pears (continued)
                                  Rate            Interval         Residues*
    Crop                Year      a.i.            (days)           (ppm)
    Pears                                            7              3.3-4.4      (0.06-0.1)
    (continued)                                     14              2.8          (0.06)
                                                    21              1.12-1.32    (0.03)

    Peaches                       0.03%              0              8.3          (0.05)
                                                     7              3.7-4.1      (0.07-0.08)
                                                    14              3.2-3.3      (0.07-0.08)
                                                    21              1.6-1.7      (0.06)
                                                    28              0.94-1.12    (0.02)
                                  0.09%              0              14.1         (0.13)
                                                     7              7.0-9.3      (0.19)
                                                    14              6.4-6.7      (0.17)
                                                    21              3.4-4.0      (0.15)
                                                    28              2.3-2.4      (0.07)
                                  0.03%              0              8.7-12.0     (0.03)
                                                    15              1.25-2.2     (0.02)
                                                    30              0.38-0.40   (<0.02)
                                                    45              0.15-0.35

                                  0.03%             58 (fresh)      0.03
                                                    72 (dried)     <0.1
                                  0.09%             58 (fresh)      0.1-0.18
                                                    72 (dried)      0.1

                                  0.03%              0              4.5-5.9      (0.13-0.17)
                                                     7              2.5-3.4      (0.12-0.18)
                                                    14              1.26-1.45    (0.06)
                                                    22              0.61-0.64    (0.03)
                                                    30              0.36-0.40    (0.02)

    Plum                          0.05%              0              0.14        (<0.02)
    (including                                       7
    prune)                                          14              0.10-0.13
                                                    21              0.07
                                                    28              0.03-0.09
                                  0.05%              0              0.22-0.25
                                                     7              0.38-0.41
                                                    14 )            0.12-0.13
                                                    21 )
                                                    28              0.06

                                  0.03%              1              0.53-0.67   (<0.02)
                                                    13              0.16-0.28
                                                    27              0.11-0.15
                                  0.03%              0              0.91-1.06    (0.02)
                                                     5              0.45-0.58
                                                    12              0.29-0.71
                                                    20              0.18-0.22

                                  Rate            Interval         Residues*
    Crop                Year      a.i.            (days)           (ppm)
    Plum                          0.03%             24 (fresh)      0.18-0.21
    (cont'd)                                           (dry)        0.02
                                                    39 (fresh)      0.06-0.08
                                                       (dry)       <0.02

    Grapes-Thompson     1963      2 kg/ha            0              5.2-5.3      (0.04)
     Seedless                     (dust)             5              2.4-2.8      (0.06)
                                                    12              0.9-1.5      (0.05)
                                                    29              0.25-0.5     (0.02)

    Grapes-Thompson     1963      2.3 kg/ha          0              9.0-9.4      (0.06-0.08)
     Seedless                     (dust)            14              1.6-2.8      (0.05-0.08)
                                                    28              0.8-1.3      (0.02-0.06)
                                                    43              0.24-0.27    (<0.02)

    Grapes-Thompson     1963      2.2               31 (fresh)      0.51-0.54
     Seedless                                       49 (dry)        0.16-0.21
                                  1.7               29 (fresh)      0.35-0.42
                                                    63 (dry)        0.07
                                  2.2               29 (fresh)      1.5-4.3
                                                    63 (dry)        0.32-0.52
                                  2.2               50 (fresh)      0.39-0.40
                                                    84 (dry)        0.11-0.18
    Grapes-Thompson     1963      2.2                0              3.0          (0.02)
     Seedless                                        9              1.87-3.1     (0.03)
                                                    21              1.33-1.96    (0.04)
                                                    28              0.34-0.46    (<0.02)
                                                    42              0.15-0.54

    Grapes-Thompson     1963      2.2                0              6.1-6.2      (0.04)
     Seedless                                        7              3.5-3.7      (0.04)
                                                    15              1.6-2.2      (0.04)
                                                    21              0.7-1.3      (0.02)
                                                    31              0.51-0.54    (<0.02)

    Grapes-Thompson     1963      1.7                7              0.65-1.09    (<0.02)
     Seedless                                       21              0.87
                                                    29              0.35-0.52
                                  2.2                7              5.9-6.2      (0.03)
                                                    21              2.1-4.6      (0.05)
                                                    29              1.31-4.3     (0.04)

    Grapes-Thompson     1963      2.0                0              9.4-13.6     (0.05-0.09)
     Seedless                     (dust)             7              2.6-3.5      (0.03-0.05)
                                                    16              1.3-2.0      (0.04)
                                                    21              0.3-0.6      (<0.02)
                                                    28              0.1-0.17

                                  Rate            Interval         Residues*
    Crop                Year      a.i.            (days)           (ppm)

    Grapes Thompson     1962      0.7 kg/ha          0              1.01         (0.02)
     Seedless                                       13              0.16        (<0.02)
                                                    31              0.03        (<0.02)
                                                    45             <0.02

    Grapes-Thompson     1962      2.0 kg/ha          0              0.60         (0.02)
     Seedless                     (dust)            14              0.05        (<0.02)
                                                    28             <0.02

    Grapes-Thompson     1962      2.0 kg/ha          7              0.36-1.22    (0.03)
     Seedless                     (dust)            14              0.05-0.16   (<0.02)
                                                    28              0.03-0.04   (<0.02)
                                                    49             <0.02

    Grapes-Thompson     1962      0.7 kg/ha         57             <0.02
     Seedless                     (3 sites)                         fresh or dried

    Grapes-Thompson     1962      0.7 kg/ha         45             <0.02
     Seedless                     (2 sites)         60             <0.02
                                                                    fresh or dried

    Muscat              1962      0.7 kg/ha         57 (fresh)     <0.02
                                                    83 (dried)     <0.02

    Cucumber            1963      0.06%             16              0.5

    Cucumber            1963      0.15%              7              0.5
                                  (greenhouse)      12              0.3
                                                    15              nil
                                  0.2%               7              1.0
                                                    12              0.2
                                                    15              0.5

    Nectarine           1962      1.8 kg/ha          0              0.61        (<0.02)
                                                     7              0.24        (<0.02)
                                                    15              0.09        (<0.02)
                                                    29              0.04        (<0.02)
                                                    44             <0.02

    Nectarine           1962      1.8               29             <0.02

    Nectarine           1962      2.2                0              0.71        (<0.02)
                                                     7              0.52-0.54
                                                    15              0.24-0.27
                                                    21              0.15-0.17
                                                    28              0.11-0.12
                                                    43              0.06

                                  Rate            Interval         Residues*
    Crop                Year      a.i.            (days)           (ppm)
    Nectarine           1963      1.7                0              0.87-0.90   (<0.02)
                                                    13              0.26-0.29
                                                    28              0.08-0.11
                                                    42              0.06-0.08

                                  2.2                0              1.03-1.19   (<0.02)
                                                    13              0.44-0.49
                                                    28              0.22-0.23
                                                    42              0.10-0.11

    * Data in parentheses are for free dinoseb

    In plants

    The rate of loss of binapacryl from leaf surfaces is fast. In the
    spraying experiment on plum trees using the 40 percent E.C., initial
    leaf deposits averaged 95 ppm; these fall to 5 ppm after two weeks and
    to less than 0.2 ppm after four weeks (Farbwerke-Hoechst AG.). The
    rate of disappearance from fruit surfaces, reported from many
    supervised trials is lower; it is usually logarithmic with time.

    The presence of small amounts of unesterified dinoseb, or fairly rapid
    hydrolysis of small amounts of binapacryl, may account for the
    bleaching of foliage on certain pear varieties (Kirby and Bennett,
    1967) and on several apple varieties (Slade, 1966; Kirby,
    unpublished). Residue analyses from the U.S.A. report the presence of
    traces of dinoseb on various fruits sprayed with binapacryl, but these
    are rarely much above the limit of detection (0.03 ppm); Maier-Bode
    (1968) could not find any free dinoseb. Considerable foliar scorch
    occurred on rooted shoots of apple kept at 100 percent R.H. after
    dipping in 100 to 200 ppm suspensions of binapacryl as the 25 Percent
    W.P.; plants dipped and maintained at normal glasshouse humidities
    were unaffected (Kirby et al., 1964). French bean (Phaseolus
    vulgaris) leaves were treated with binapacryl at 1.5 mg per 30 cm2
    and maintained at 22°; if the R.H. was 100 percent, no dinoseb was
    detected at any time, but at 40 percent traces of dinoseb (0.04 1.19
    from 8 to 10 leaves) were found during the course of a week
    (Farbwerke-Hoechst AG.).

    In soils

    Evidence has been obtained that degradation of binapacryl that occurs
    in muck soil in due to microbial action (Chin and Stanovich, 1965).

    Evidence of residues in food in commerce or at consumption

    No report of binapacryl residues in foodstuffs being sold or prepared
    for consumption has been seen so far.


    Residue of binapacryl can be determined by several colorimetric
    procedures applicable to dinitrophenol compounds, provided a
    hydrolysis stage is included in the sample preparation, The methods of
    Schechter and Haller (1944), Kilgore and Cheng (1963), Potter (1963)
    and Abbott and Thomson (1964) are suitable for the resultant
    dinitrobutylphenol (dinoseb). Buxton and Mohr (1968) recommend a
    procedure based on the colour formed when binapacryl, or its principal
    decomposition product dinoseb, is treated with pyridine, optical
    densities being read at 435 nm. A sensitivity of about 0.03 ppm of
    binapacryl is achieved by this method which has been used on stone and
    pome fruits, strawberries, grapes and cucurbits; it is not
    sufficiently sensitive for hops or cottonseed. Residues of
    dinitrophenols arising from other sources would also be included in
    the figures obtained.

    An electron-capture gas chromatographic method is also mentioned by
    Buxton and Mohr (1968) but no details are given. The separatory
    systems used by Clifford and Watkins (1968) for dinitroalkylphenols
    and by Boggs (1966) and Yip and Howard (1968) for their methyl ethers
    should be applicable to the determination of hydrolysed binapacryl
    residues. The development and evaluation of such methods for
    regulatory purposes is desirable.


        Country                    Crop               Tolerance (ppm)

    Australia                Pome and stone fruits         2.0*

    Belgium                  Fruits and vegetables         0.3

    Canada                            do.                  1.5

    France                            do.                  0.3

    Germany (Fed. Rep.)               do.                  0.3

    Italy                             do.                  0.3

    Luxembourg                        do.                  0.3

        Country                    Crop               Tolerance (ppm)

    Netherlands                       do.                  0.3

    United States of America          do.                  0.22*

    * These levels are provisional


    Binapacryl is a non-ovicidal acaricide and a fungicide of economic
    value against powdery mildews only. Its use on apple is widespread in
    Europe and Australasia, but very limited so far in North America. Use
    on other fruits and other crops appears to be slight. Mitotoxicity on
    apple and pear under some circumstances is a drawback. No use on
    animals is known. The technical product is claimed to contain 96
    percent binapacryl; nature of impurities not reported. Wettable
    powders are now being supplemented by stable aqueous suspensions.

    Residues from recommended applications normally fall to less than 1
    ppm on pome, stone and soft fruits within one week after the final
    application, this being the minimum pre-harvest interval. The
    persistence (half-life) of the technical a.i. is reported to be short.

    Non-toxicity of binapacryl will depend on the stability of the ester
    linkage; this stability seems to be great in the mammalian food tract.
    Traces of dinoseb are sometimes found on fruit sprayed with
    binapacryl, but these are rarely above the limit of detection (0.03
    ppm). There is very little dermal absorption. Metabolites found
    include the monoamino reduction product and an acid formed by
    oxidation of the s-butyl side-chain.



    Apples, pears, grapes         0.5 ppm

    Plums                         0.3 ppm

    Nectarines                    0.2 ppm

    Peaches, cherries             1 ppm



    1. Further work on the absorption and the excretion rates in rats or
       other species.

    2. Reproduction and teratogenicity studies in a non-rodent mammalian

    3. More studies on possible cataract formation in animals.

    4. Further information on the unidentified fraction of the technical

    5. Residue data from countries other than the U.S.A.

    6. The development and evaluation of a GLC method suitable for
       regulatory purposes.


    Abbott, D.C. and Thomson, J. (1964) Wedge-layer clean-up of dinoseb
    extracts. Analyst, 89:613-5

    Baran, J., Fancher, O.E. and Calandra, J.C. (1966) Two-year oral
    toxicity of NIA-9044 (Morocide) - beagle dogs. Unpub. Rept. from
    Industrial Bio-test Laboratories Inc., to Niagara Chemical Division,
    FMC Corporation, submitted by Farbwerke Hoechst AG.

    Boggs, H. (1966) Gas chromatography of dinitro herbicides. J. Assoc.
    Offic. Anal. Chem. 49:772-3

    Bough, R.G., Cliffe, E.E. and Lessel, E. (1965) Comparative toxicity
    and blood level studies on binapacryl and DNBP. Toxicol. appl.
    Pharmacol., 7:353-60

    Buxton, R.W. (1962) R-522. Morocide (Residues on fresh and dried
    grapes, peaches and pears). Niagara Chem. Div., FMC Corp., New York.
    Unpub. Rept.

    Buxton, R.W. (1963) R-674. Morocide (Residues on peaches). Niagara
    Chem. Div., FMC Corp.,  New York. Unpub. Rept.

    Buxton, R.W. and Mohr, T.A. (1968) in, Analytical Methods for
    Pesticides, Plant Growth Regulators and Food Additives, ed. by G.
    Zweig, Vol.V, pp.239-42

    Cervenka, H. and Kay, J.F. (1963) Cataractogenic studies. Unpub. Rept.
    from Industrial Bio-test Laboratories Inc., to Niagara Chemical
    Division, MC Corporation, submitted by Farbwerke Hoechst AG.

    Chin, W.T. and Stanovich, R.P. (1964) Metabolism of Morocide by dogs.
    Unpub. Rept. M-1431,  from the Research and Development Department,
    Niagara Chemical Division, FMC Corporation, submitted by Farbwerke
    Hoechst AG.

    Chin, W.T. and Stanovich, R.P. (1965) M-1604. Biological influence on
    the hydrolysis of  Morocide in muck soil. Niagara Chem. Div., FMC
    Corporation, New York. Unpub. Rept.

    Clifford, D.R. and Watkins, D.A.M. (1968) The gas chromatography of
    dinitroalkyl phenols. J. Gas Chromatog., 6:191-2

    Edson, E.F., Sanderson, D.M.. and Noakes, D.N. (1966) Acute toxicity
    data for pesticides (1966).  World Revue of Pest Control, 5:143-51

    Emmel, L. (1960) Uber ein neuartiges Akarazid auf Basis van
    Dinitroalkylphenylacrylat.  Meded. LandbHogesch. OpzoekStns, Gent,

    Ernst, W. and Bär, F. (1964) Die Unwandlung des
    2,4-Dinitro-6-sec-butyl-phenols und seiner Ester im tierischen
    Organismus. Arzneimittel.-Forsch., 14:81-4

    Farbwerke-Hoechst AG. (1969) Binapacryl. Unpub. Rept.

    Hoechst. (1962) Chronische Toxizitätsstudien mit Acricid = Hoechst
    2784 über 2 Jahre an Ratten. Unpub. Rept. submitted by Farbwerke
    Hoechst AG.

    Hoechst. (1964) Prüfung van Acricid-Wirkstoff (Binapacryl) auf akute
    orale Toxizität an Ratten, Kaninchen und Hunden. Unpub. Rept.
    submitted by Farbwerke Hoechst AG.

    Industrial Bio-test Laboratories Inc. (1964) Status summary. Chronic
    oral toxicity of Nia  9044 (Morocide). Albino rats. Unpub. Rept. to
    Niagara Division, FMC Corporation, submitted by Farbwerke Hoechst AG.

    Kennedy G. and Calandra, J.C. (1965a) Three generation reproduction
    study in albino rats on Morocide: first generation. Unpub. Rept. from
    Industrial Bio-test Laboratories Inc., to Niagara Chemical Division,
    FMC Corporation, submitted by Farbwerke Hoechst AG.

    Kennedy, G. and Calandra J.C. (1965b) Three generation reproduction
    study on Morocide - Albino rats: Second generation. Unpub. Rept. from
    Industrial Bio-test Laboratories Inc. to Niagara Chemical Division, MC
    Corporation, submitted by Farbwerke Hoechst AG.

    Kennedy, G. and Calandra, J.C. (1965c) Three generation reproduction
    study on Morocide - Albino rats: Final report. Unpub. Rept. from
    Industrial Bio-test Laboratories Inc., to Niagara Chemical Division,
    FMC Corporation, submitted by Farbwerke Hoechst AG.

    Kilgore, W.W. and Cheng, K.W. (1963) Extraction and determination of
    Karathane residues in fruits. J. Agr. Food Chem., 11:477-9

    Kirby, A.H.M., Frick, E.L., Hunter, L.D., and Tew, R.P. (1964)
    Relative fungitoxicities of some dinitroalkylphenols. Tetrahedron, 20:
    Suppl. 1, 483:508

    Kirby, A.H.M. and Bennett, M. (1967) Phytotoxicity to pear of some
    fungicides controlling powdery mildews. Rep. E. Malling Res. Stn. for
    1966, 181-5

    Maier-Bode, H. (1968) Uber die Persistenz des Akarazids Binapacryl. Z.
    PflKrnankh. PflPath. PflSchutz, 75:321-7

    Potter, J.A. (1963) The determination of dinoseb in potatoes. Analyst,

    Schechter, M.S. and Haller, H.D. (1944) Colorimetric determination of
    2,4-dinitroanisole. Ind. Eng. Chem. Anal. Ed., 16:325-6

    Slade, D.A. (1966) New fungicides for apple disease control. Orchard.
    N.Z., 39:393-7

    Spencer, H.C., Rowe, V.K., Adams, E.M. and Irish, D.D. (1948)
    Toxicological studies on laboratory animals of certain
    alkyldinitrophenols used in agriculture. J. Industr. Hyg. Toxicol.

    Stanovick, R.P. (1963) M-1204. Determination of Morocide and
    dinitrobutylphenol residues on apples, pears and cucumbers. Niagara
    Chem. Div., FMC Corporation, New York. Unpub. Rept.

    Versier, R. (1965) Evolution at importance des résidus de fongicides
    utilisés en arboriculture fruitière. Congr. Internat.
    d'Antiparasitaires, Naples

    Yip, G. and Howard, S.F. (1968) Extraction and clean-up procedure for
    the gas chromatographic determination of four dinitrophenol
    pesticides. J. Assoc. Offic. Anal. Chem. 51:24-28

    See Also:
       Toxicological Abbreviations
       Binapacryl (ICSC)
       Binapacryl (WHO Pesticide Residues Series 4)
       Binapacryl (Pesticide residues in food: 1984 evaluations)
       Binapacryl (Pesticide residues in food: 1985 evaluations Part II Toxicology)