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    PESTICIDE RESIDUES IN FOOD - 1981


    Sponsored jointly by FAO and WHO






    EVALUATIONS 1981







    Food and Agriculture Organization of the United Nations
    Rome

    FAO PLANT PRODUCTION AND PROTECTION PAPER 42

    pesticide residues in food:
    1981 evaluations

     the monographs

    data and recommendations
    of the joint meeting
    of the
    FAO panel of experts on pesticide residues
    in food and the environment
    and the
    WHO expert group on pesticide residues

    Geneva, 23 November-2 December 1981

    FOOD AND AGRICULTURE ORGANIZATION OF THE UNITED NATIONS
    Rome 1982

    PROCYMIDONE

    IDENTITY

    Common name              procymidone (ISO)

    Chemical name (IUPAC)    N-(3,5-dichlorophenyl)-l,2-
                             dimethylcyclopropanedicarboximide

    CAS                      3-(3,5-dichlorophenyl)-l,5-dimethyl-3-
                             azabicyclo (3.1.0) hexane-2,4-dione

    Synonyms                 Campilex (R), S-7131, Salithiex (R)
                             Sialex (R) Sumiboto (R) Sumicros (R)
                             Sumilex (R), Sumisclex (R)

    Empirical formula        C13 H11 Cl2 NO2

    Structural formula

    CHEMICAL STRUCTURE 1

    Other information on identity and properties

    Molecular weight         284.13

    State                    White to light brownish crystalline solid
    (technical material)

    Specific gravity         d25
                              25 1.42 - 1.46

    Vapour pressure          1.32  10-4 mm Hg at 25C

    Solubility               Acetone 18.0, acetonitrile 10.1,
    (% w/w at 25C)          cyclohexanone 14.8, ethyl acetate 11.5,
                             methanol 1.6, xylene 4.3

    Solubility in water      4.5 mg/l at 25C

    n-octanol/water
    partition co-efficient   1.3834  103 at pH 7.26

    Stability                Stable in solvents, unstable in alkaline
                             media. No significant breakdown after 20
                             weeks storage at 60C.

    Formulation              Currently available as 50% wettable powder
                             and 265 and 500 g/l emulsifiable concentrate

    Purity of technical
    product                  Contains normally 95-99% of procymidone.
                             Detailed information on the impurities in
                             technical procymidone ranging from 0.1-1% was
                             reported to the Meeting.

    RESIDUES IN FOOD

    USE PATTERN

         Procymidone is a recently introduced moderately systemic
    fungicide with a rather selective action. It is especially effective
    in the control of  Botrytis and  Sclerotinia species on various
    vegetables, fruits, flower crops and ornamentals. It is also used on
    stone fruits against  Monilia sp.

         There are some indications that the fungicide may affect mitosis
    in susceptible fungi but the actual site of action has not been
    elucidated.

         Procymidone is effective against  Botrytis strains that have
    acquired resistance to benzimidazole compounds; the latter also have
    an antimitotic action in fungi owing to interference with the
    functioning and assembly of microtubules, the elements of the spindle.
    It is assumed that the site of action of procymidone in the mitotic
    process is different from that of the benzimidazole compounds.

         Procymidone is applied, often repeatedly, on the aerial parts of
    fruits and vegetables and sometimes until shortly before harvest to
    avoid fruit- and vegetable-rot during transport and distribution. It
    is also used on young plants and/or the top layer of soil against
    soil-borne diseases  (Sclerotinia, Botrytis).

         Products containing procymidone are registered and/or approved in
    many countries, in Asia, South America and Europe as well as in
    Australia and New Zealand. They are mainly used against grey mould
    (mainly  Botrytis cinerea), onion grey mould  (Botrytis squamosa), 
    onion neck-rot  (Botrytis aclada allii), Sclerotinia spp. and
     Monilia sp. (brown rot on peaches etc., blossom blight and twig wilt
    on cherries, etc.).

         The current suggested uses are summarized in Tables 4 and 5.
    Recommended pre-harvest intervals known to the Meeting are listed
    under national maximum residue limits.

    RESIDUES RESULTING FROM SUPERVISED TRIALS

         Many supervised residue trials have been carried out on a wide
    variety of fruits and vegetables and also on rice and oilseeds. See
    Tables 6 and 7 for details.

    Fruits

    Pome fruits

         Residue data were obtained only on apples from Japan. Procymidone
    levels were less than 3 mg/kg 21 days after the last of 3 to 5
    treatments, but had risen to about 3 mg/kg 35 days after the last of 5
    treatments.

    Stone fruits

         Residue data on cherries were available from Australia, Hungary
    and Japan. Procymidone levels were generally less than 5 mg/kg one day
    or more after the last treatment, except one erratic sample in
    Australia which contained 6.2 mg/kg.

         Residue levels in peaches were generally less than 2 mg/kg three
    or more days after the last application of 0.2 to 3 kg/ha (recommended
    application rates are 0.75 to 1.5 kg/ha.

         In a trial in New Zealand, nectarines sprayed 7 times at
    0.75 kg/ha contained procymidone at or below 0.21 mg/kg.

         In a trial in France, the residue on plums after a single
    application of procymidone at 0.75 kg a.i./ha was 2.4 mg/kg at day 0
    (4 h after spraying) and 1.3 mg/kg 8 days later.

    Berry fruits

         Residue data on grapes were obtained from several countries in
    Europe, from New Zealand and South Africa, where 1 to 5 treatments
    were carried out at rates of 0.5 to 1.25 kg/ha. About 14 days after
    the last treatment, procymidone residues were in the range of 0.4 to
    9.3 mg/kg and declined to 0.6 to 5.1 mg/kg after 35 to 36 days.

         Residue data were obtained on strawberries grown outdoors and in
    glasshouses or plastic tunnels. The procymidone residues were 0.8 to
    14.3 mg/kg 0 to 1 day after the last spraying and declined to 0.8 to
    6.5 mg/kg after 6 to 8 days. The residue levels after 14 to 15 days
    were generally 2 mg/kg or less.

        TABLE 4.  Use patterns of procymidone on fruits, registered and/or approved uses
                                                                                                                                             

                                                                       Country
                                                                                                                                             

                                    Fed.Rep.
                                    of
    Crop                   France   Germany  Luxembourg   Spain  Switzerland   UK   Bulgaria   Czechoslovakia   Hungary   Romania  Yugoslavia
                                                                                                                                             

    Black currant                                                              X

    Grape                  X        X        X            X      X             X    X          X                X         X        X
    (incl. table grapes)

    Peach                                                                                                       X

    Raspberry                                                                  X                                X

    Stone fruits                                                                                                X

    Strawberry                                            X                    X    X                           X
                                                                                                                                             

    Table 4 (continued)
                                                                                                                                             

                                                                   Country                                       Range of application
                                           South                                              New       Target   rates in various countries
    Crop                   Greece  Turkey  Africa  Chile  Uruguay  Japan  Lebanon  Australia  Zealand   fungi1   (kg a.i./ha  (g a.i./100 l)
                                                                                                                                             

    Black currant                                                                                                0.75

    Grape                  X       X       X       X      X               X                   X         Bc       0.5 - 1.0    25 - 75
    (incl. table grapes)

    Peach                                                          X                                    M        0.5 - 0.75   33 - 50

    Raspberry                                                                                           Bc       0.5 - 0.75

    Stone fruits                                                          X        X          X         Bc M     0.6 - 1.0    25 - 75

    Strawberry                                            X        X      X                   X         Bc       0.4 - 0.75   25 - 100
                                                                                                                                             

    1  Bc = grey mould Botrytis sp., mainly Botrytis cinerea;
    M  = Monilia, including Monilinia fructigena and M. fructicola (brown rot, blossom blight and twig blight).

    TABLE 5.  Use patterns of procymidone on vegetables and oil seeds; registered and/or approved uses
                                                                                                                                             

                           Countries
                           Europe                         Asia                                                Range of application
                                                                                         New        Target    rates in various countries
    Crop                   France  UK  Hungary   Greece   Japan  Korea  Lebanon  Taiwan  Zealand    fungi1    (kg a.i./ha     (g a.i./100 l)
                                                                                                                                             

    Beans (not specified)  X                                            X                X          Bc Sc     0.5-0.75        25-50

    Azuki bean                                            X                                         Bc                        50

    Kidney bean                                           X                                                                   25-50

    Soybean                                               X                                         Sc                        25-50

    Celery                                                X                                         Sc                        25-50

    Cucumber                                              X                                         Bc Sc                     25-50

    Eggplant                                              X                                         Bc Sc                     25-50

    Lettuce                X       X                      X                      X       X          Bc Sc     0.4-0.75        25-50

    Melon                  X                                                                        Bc Sc     0.75

    Onion                                                 X                                         Bsq Baa                   50

    Pepper (green)                                        X                                         Bc Sc                     25-50

    Potato                                                X                                         Sc                        33-50

    Tomato                         X                      X                              X          Bc Sc     0.5             25-50

    Vegetables (general)               X         X                      X                                     0.5             25-50
                                                                                                                                             

    TABLE 5.  (con't)
                                                                                                                                             

                           Countries
                           Europe                         Asia                                                Range of application
                                                                                         New        Target    rates in various countries
    Crop                   France  UK  Hungary   Greece   Japan  Korea  Lebanon  Taiwan  Zealand    fungi1    (kg a.i./ha     (g a.i./100 l)
                                                                                                                                             

    Rape seed                                                    X                                  Sc                        50

    Sunflower                          X                                                            Bc        0.5
                                                                                                                                             

    1  Bc = grey mould, mainly Botrytis cinerea;
       Sc = Sclerotinia spp.;
       Bsq = Botrytis squamosa;
       Baa = Grey mould neck rot = Botrytis aclada allii.

    TABLE 6.  Residues of procymidone resulting from supervised trials in fruits and vegetables
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  01/1       3/4        6/8        14/16      20/22      26/29      35/36
                                             (kg         (%)
                                             a.i./ha)
                                                                                                                                                

    Grape         France       1977/80  1    0.75       wp 50%                                                 0.53
                                        1    0.75       EC500g/l                                               0.48
                                        4    0.75       wp 50%     5.0 4.8               4.7 4.5    4.8 4.9    3.4 3.6

    Table
    grapes                     1980     4    0.75       wp 50%     3.4 3.1               1.7 1.4    1.3 1.5    0.9 1.0    0.9 0.8
    (")                        1980     4                          2.0 2.0               1.8 1.6    2.5 2.3    1.6 1.4    1.0 1.1
                               1977     1    0.75       wp 50%                                                 2.46
                                                                                                              (2.09-5.10)
                                        1    1.0        wp 50%                                                 3.89
                                                                                                              (1.76-5.42)
                               1977    >1    0.75       wp 50%     4.9                   4.4        3.2        3.3
                               1977    >1    0.75       wp 50%     6.4                   3.1        2.2        2.8

                  Fed.Rep.
                  of Germany   1976/77  5    1.25       wp 50%    11.2                              8.4        2.4        2.1
                               "        5    1.25       wp 50%                                      9.3       10.1        6.6        5.1
                               "        5    1.25       wp 50%     7.2                              5.7        5.9        5.2        2.4
                               "        4    1.25       wp 50%     8.0                              5.6        4.2        3.7        0.6
                               "        4    1.25       wp 50%     4.2                              3.7                   3.2        2.9
                               "        4    1.25       wp 50%     5.0                              3.7        2.4        2.0        1.9
                               "        5    0.9        wp 50%     3.7                              2.5        1.9        1.6        1.2
                               "        5    0.9        wp 50%     6.1                              3.0        2.5        2.4        1.4
                               "        5    0.9        wp 50%     5.1                              3.4        2.8        2.1        1.7

                  Italy        1976/77  4    0.85       wp 50%                                                            1.9 0.9
                               "        4    1.28       wp 50%                                                            4.1 1.6
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  01/1       3/4        6/9        14/16      20/22      26/29      35/36
                                             (kg         (%)
                                             a.i./ha)
                                                                                                                                                

    Grape         New
                  Zealand      1979     1    0.7        wp 50%                1.7        1.7        1.0        1.6
                                             1.05       wp 50%                2.6        4.3        2.7        2.5

                  Spain        1976     3    7.5 g/
                                            100 1       wp 50%                           4.4        4.0        3.0        2.7
                                            12.5 g/
                                            100 l       wp 50%                           6.8        6.8        5.3        4.0

    Table         South
    grapes        Africa       1978     1    0.7        dust       0.7 0.7    0.3 0.4    0.5 0.5    0.4 0.4
                                        1x4  0.75 +     wp 50 +
                                             0.7        dust 3%    0.6 0.6    0.5 0.6    0.5 0.5    0.4 0.4

                  UK           1978     1    0.75       wp 50%                           7.9

                                                                                                                                                

                                                                  0/1         3/4        7/9         14         21         28         35
                                                                                                                                                

    Apple         Japan        1979     3    3          wp 50%                                                 ng 2.0                2.1 2.3
                                        5    3          wp 50%                                                 1.2 1.1               1.2 1.3

    Black
    currant       UK           1979     3    0.75       wp 50%     5.3                   4.2
                                        1    0.5        wp 50%     6.0        7.0        3.3        3.5        2.1
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  0/1         3/4        7/9         14         21         28         35
                                             (kg         (%)
                                             a.i./ha)
                                                                                                                                                

    Cherry        Australia    1977     5   19 g/
                                            100 l       wp 50%     3.3 2.4
                                            525 g/
                                            100 l       wp 50%     2.0 2.1
                                        5   37.5 g/
                                            100 l       wp 50%     6.2 2.9

                  Japan        1977     1    3.5        wp 50%                           1.9        1.0        1.7
                                        3    3.5        wp 50%                           3.6        2.3        1.7
                                        3    3.5        wp 50%                           1.1        1.0        0.6
                                        5    3.5        wp 50%                           1.3        1.2        1.1

    Peach         Australia    1978    2-9  19 g/
                                            100 l       wp 50%     2.6
                                                                  (2.4-5.1)
                                            25 g/
                                            100 l       wp 50%     4.1
                                                                  (1.6-7.6)
                                            37.5 g
                                            /100 l      wp 50%     6.3
                                                                  (2.3-11.7)

                  Japan        1977     4    3          wp 50%
    peel                                                                     73.9       72.8       43.2
    pulp                                                                      1.1        1.1        0.8
                               1977     6    3          wp 50%
    peel                                                                     51.2       44.5       29.0
    pulp                                                                      1.2        1.1        1.0
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  0/1        3/4        6/9         14      20/21         28         35
                                             (kg         (%)
                                             a.i./ha)
                                                                                                                                                

                  New
                  Zealand      1980     7    0.75       wp 50%     0.42                  0.4        0.4
                                        7    0.75       wp 50%     0.6        0.8        0.5        0.3
                                        5    1.5        wp 50%     0.3        0.4        0.9        0.6
                                            210 g/
                                            100 l       wp 50%     0.4        0.7        0.4        0.3
                                        2   20g/
                                            100 l       wp 50%     1.7        1.1        1.3        1.1
                                            230 g/
                                            100 l       wp 50%     2.4        1.1        1.2        0.3

    Nectarines    New
                  Zealand      1980     7    0.75       wp 50%     0.1        0.2        0.1        0.1

    Plum          France       1979     1    0.75       wp 50%     2.4                   1.3

    Raspberry     Poland       1980     2    1.25       wp 50%     1.7                   0.25
                                                                  (1.6-1.9)             (0.2-0.3)

                  UK           1978     1    0.75       wp 50%                           0.3
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  0/1        3/4        6/9         14      20/21         28         35
                                             (kg         (%)
                                             a.i./ha)
                                                                                                                                                

    Kiwifruit     New
                  Zealand      1980/81  6    1.1        wp 50%     4.4        2.6        5.9        2.8        2.0
    (flesh only)                                                   0.5        0.4        0.25
                               1980/81  6    1.1        wp 50%     6.3        6.7       11.4        5.4        3.3
    (flesh only)                                                   1.8        2.1        0.8
                                            6100 g/
                                            100 l       wp 50%     5.3        4.7        8.7        4.1        2.6
                                            450 g/
                                            100 l       wp 50%                           2.9        3.0        1.9

                                                                                                                                                

                                                                   0/2        3/4        5/6        7/8        9/10      13/15      16/19
                                                                                                                                                

    Strawberry    France       1979     1    0.75       wp 50%                                      0.4                   0.3
    outdoors                   1979     2    0.75       wp 50%                                      1.0                   0.1
                               1980     3    0.75       wp 50%     4.9 5.2    2.1 2.4               1.9 2.0               0.7 0.5
                               1980     3    0.75       wp 50%     3.8 3.6    2.1 1.9               1.3 1.4               0.4 0.4
                               1980     3    0.75       wp 50%     2.9 2.7    2.3 2.3               1.1 1.1               0.2 0.3
                               1980     3    0.75       wp 50%     3.8 3.6    2.3 2.2               1.3 1.2               0.3 0.3
                               1978     3    0.5        wp 50%     2.1                              1.5                              0.9
                               1978     3    0.75       wp 50%     3.0                              1.3                              0.8
                               1978     4    0.75       wp 50%                3.6                                                    1.5
                               1978     3    0.5        wp 50%                                                                       0.93
                               1978     3    o.75       wp 50%                                                                       1.83
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  0/2        3/4        5/6        7/8        9/10      13/15      16/19
                                             (kg         (%)
                                             a.i./ha)
                                                                                                                                                

                  Fed.Rep.
                  of
                  Germany      1976     3    1.5        wp 50%     1.1        0.9                   0.8                   0.6
                               1976     3    0.95       wp 50%     1.7        1.4                   1.1                   0.9

                  Italy        1977     3    0.26       wp 50%                                                            0.7
                                        3    9.39       wp 50%                                                            0.7
                                        3    9.59       wp 50%                                                            1.2
                                        3    0.78       wp 50%                                                            2.7

    Strawberry    Netherlands  1977     1    0.75       wp 50%     1.1                                         0.4
    outdoor                                                       (0.3-2.7)                                   (0.2-0.6)
                                        1    0.75       wp 50%                2.1                   2.0                   1.2
                                                                             (0.8-3.1)             (1.2-2.9)             (0.6-2.1)

                  Poland       1980     2    1.25       wp 50%     6.9                   5.0                   3.6        1.1        0.8
                                                                  (6.5-5.1)             (4.9-5.1)             (3.3-4.0)  (1.0-1.2)  (0.7-0.9)

                  UK           1980     1    0.75       wp 50%     2.5
                                                                  (1.9-3.1)
                                        1    1.5        wp 50%     1.8
                                                                  (1.6-1.9)
                               1980     1    0.75       wp 50%     4.5                              2.4
                                                                  (4.1-4.8)                        (2.0-2.7)
                                             1.5        wp 50%     3.9                              3.2
                                                                  (3.5-4.4)                        (3.0-3.5)
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  0/2        3/4        5/6        7/8        9/10      13/15      16/19
                                             (kg         (%)                                                                        1)23 2/35
                                             a.i./ha)
                                                                                                                                                

    glasshouse    Japan        1975     3    0.6        wp 50%     6.2 7.8    4.0 4.4               2.4 2.6
                                        6    0.6        wp 50%    12.3 14.3   6.6 8.0               ~. 7 6.5
                                        3    0.65       wp 50%     0.7 0.8    1.1 1.8    0.6 0.8
                                        6    0.65       wp 50%     1.2 1.4    1.1 1.2    0.8 0.8
                               1975     3    0.65       wp 50%                1.6 1.6               0.8 0.8               0.4 0.4
                                        6    0.65       wp 50%                0.9 1.0               0.9 1.0               0.3 0.3
                               1976     3    0.5        wp 50%                1.2                   1.0                   0.5
                                        6    0.5        wp 50%                1.8                   1.4                   0.9

    plastic
    tunnels       UK                    3    0.75       wp 50%                                                                       1.84
                                        2    0.75       wp 50%                                                                       0.65

                                                                                                                                               
                                                                                                 Days
                                                                   1         4/5        8/10       12/14     15/16  19/21   27/28
                                                                                                                                               

    Beans
    kidney
    bean          France       1978     1    0.75       wp 50%                0.2
                                        1    1.0        wp 50%                           0.92
                                        1    1.0        wp 50%                0.4
                                        2    0.75       wp 50%                                      0.2
                                        2    1.0        wp 50%                                                      0.4
                                        1    0.75       wp 50%                           0.8
                                        1    1.0        wp 50%                           2.2
                                        1    1.0        wp 50%                           0.7
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation                                Days
                                             (kg         (%)       1         4/5        8/10       12/14     15/16  19/21   27/28
                                             a.i./ha)
                                                                                                                                                

                                        1    0.75       wp 50%                           0.1
                                        1    1.0        wp 50%                                      0.3
                                        1    1.0        wp 50%                           0.5
                               1977     2    0.75       wp 50%                                                 0.2

                                        2    0.75       wp 50%                                                      0.4
                                        2    0.75       wp 50%                                                 0.5
                  Netherlands           2    0.5        wp 50%                                                             0.21(0.10-0.21)
                                        2    0.5        wp 50%                                                             0.11(0.09-0.15)

                  New
                  Zealand               2    0.5        wp 50%     0.8        0.7        0.6        0.6
                                        2    1.0        wp 50%     1.8        1.7        1.5        1.3

                                                                                                                                                

                                                                   1          3          7          12/14         19/21       28/31
                                                                                                                                                

    Soybean       Japan        1975     3    0.5        wp 50%
    pods                                                           2.8                              1.2
    beans                                                                                                         1.7
                                        4    0.5        wp 50%
    pods                                                           2.5
    beans                                                                                                         1.5
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation  1          3          7          12/14         19/21       28/31
                                             (kg         (%)
                                             a.i./ha)
                                                                                                                                                

                                        3    0.5        wp 50%
    pods                                                           4.3                              0.6
    beans                                                                                                         1.1
    beans                               4    0.5        wp 50%                                                    1.1

    Onions
    bulb onions   Japan        1977     4    0.75       wp 50%     0.04       0.04       0.01
                                        8    0.75       wp 50%     0.06       0.06       0.05
                                        4    1.0        wp 50%     0.01       0.01       0.04
                                        8    0.5-1.0    wp 50%     0.04       0.05       0.05
                                        4    0.5        wp 50%     0.02       0.02       0.02
                                        8    0.5        wp 50%     0.04       0.03       0.04

                  Netherlands  1978     2    0.25       wp 50%                                      0.12
                                                                                                   (0.10-0.13)
                                        2    0.25       wp 50%                                      0.12
                                                                                                   (0.09-0.14)
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation                (Days)
                                             (kg         (%)       01          19            86
                                             a.i./ha)
                                                                                                                                                

    Chicory
    witloof       France       1978     1   on top
                                            of roots
                                            at forcing                        0.01

    (leaves)                                2 g m2                                          <0.01
                                            4 g m2                                           0.01

                                        1   dipping of
                                            roots

                                            2 g/m2                            0.01
    in roots
    after forcing                           2 g/m2                            0.7
                                            4 g/m2                            2.0

                                                                                                                                               

                                                                                       (days)
                                                                 0/1         3/4         6/7        13/14      21/23      26/28
                                                                                                                                               

    Lettuce
    glasshouse    France       1980     1    0.75       wp 50%                                                 0.6
                               1980     1    0.75       EC 500
                                                        g/l                                                    1.2 1.1
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation                                 (days)
                                             (kg         (%)       0/1         3/4         6/7        13/14      21/23      26/28
                                             a.i./ha)
                                                                                                                                                

                               1978     3    0.5        wp 50%    29.1        9.5        0.7
                                        3    0.75       wp 50%    47.1       12.4        0.7
                                        3    1.0        wp 50%    77.1       17.2        1.9
                               1978     1    0.75       wp 50%                                                 3.4
                               1978     5    0.75       wp 50%                                                            1.6
                               1978          0.75       wp 50%                                                 3.1

    Outdoors      Fed.Rep.
                  of
                  Germany      1978     3    0.225      wp 50%     5.1 5.3    2.3 2.5    0.7 1.1    0.1 0.2    <0.1
                               1978     3    0.225      wp 50%     2.9 3.2    1.7 2.3    1.1 0.9    0.6 0.4    <0.1

                  Japan        1977     3    1.1        wp 50%                1.3        0.8        0.2        0.4
                                        5               wp 50%                1.0        0.8        0.4        0.3
                               1977     3    0.75-1.0   wp 50%                0.02       0.01       <0.01      <0.01
                                        6               wp 50%                0.3        0.02       0.02       0.01

    glasshouse    UK           1979     4    0.25       wp 50%                           0.76
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation                      (Days)
                                             (kg                   42        47/51      56          66         88         104
                                             a.i./ha)    (%)
                                                                                                                                                

                  France       1978     4    0.5        wp 50%     0.2
                                             0.75       wp 50%     0.5
                                             1          wp 50%     0.7
                               1978     4    0.5        wp 50%                           1.0
                                             0.75       wp 50%                           2.7
                                             1.0        wp 50%                           3.8
                               1976     3    0.5        wp 50%                1.7
                                             0.75       wp 50%                3.2
                                             1.0        wp 50%                4.7
                               1978     4    0.5        wp 50%     0.8
                                             0.75       wp 50%     1.4
                                             1.0        wp 50%     1.8
                               1978     3    0.75       wp 50%                0.6
                                                                             (0.4-0.8)

    Glasshouse
    winter        Netherlands  1978     1    1          wp 50%                                                 0.06
                                             1.5        wp 50%                                                 0.08
                                             1          wp 50%                                                            0.05
                                             1.5        wp 50%                                                            0.08
                                             1          wp 50%                                      0.03
                                             1.5        wp 50%                                      0.04
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation                          (Days)
                                             (kg          (%)      0/1            3/4            7/9            10/11          13/14          21
                                                                                                                                                

    Cucumber      Japan        1976     3    1.25       wp 50%     0.34           0.12           0.09
    glasshouse                          6    1.25       wp 50%     0.33           0.16           0.11
                               1976     3    1.0-1.25   wp 50%     1.2            0.67           0.28
                                        6    0.63-1.25  wp 50%     1.2            0.82           0.32

    Gherkins      Netherlands  1978     3    0.3        wp 50%                                                  0.17
                                                                                                               (0.16-0.18)
                               1978     3    0.3        wp 50%     0.32
                                                                  (0.22-0.55)
                               1978     3    0.3        wp 50%     0.26
                                                                  (0.13-0.33)

    Melon
    (white fruit  France       1979     1    0.75       wp 50%                                   0.17 0.19      0.13 0.23
    (edible pulp                                                                                 0.06 0.12      0.08 0.12
    (edible pulp               1989     2    0.75       wp 50%     0.19           0.21           0.19                          0.19
    (peel                                                          1.6            1.3            1.4                           1.2
    (edible pulp               1980     2    0.75       wp 50%     0.28           0.32           0.28                          0.29
    (peel                                                          1.7            2.0            1.4                           0.9

    Pepper        Japan        1975     3    1.5                   3.3            1.7            1.3                           0.3
    (green)                             6    1.5                   3.0            2.5            1.5                           0.3
    glasshouse                 1976     3    1.2-1.5               3.5            2.4            1.4                           0.8
                                        6    0.7-1.5               3.8            2.7            1.6                           1.0
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation                          (Days)
                                             (kg          (%)      0/1            3/4            7/9            10/11          13/14          21
                                                                                                                                                

    Tomato
    outdoor       France       1979     6    1.5        wp 50%                                   0.30 0.32
                                        7    1.5        wp 50%                                   0.28 0.55
                               1979     1    0.75       wp 50%                                   0.19 0.22                     0.07
                               1980     3    0.75       wp 50%     2.7            1.7            1.5                           1.4            0.7
                               1980     3    0.75       wp 50%     2.0            1.7            1.4                           1.3            0.6

    glasshouse    Japan        1977     3    1.0-1.25   wp 50%     2.0            0.9            0.9                           1.0
                                        6    1.0-1.25   wp 50%     3.1            2.3            2.8                           1.4
                               1977     3    1.5        wp 50%     2.5            2.1            2.2                           2.3
                                        6    1.5        wp 50%     4.7            3.7            2.6                           2.3
                               1977     2    1.0-1.25   wp 50%                    1.6            0.9                           1.0            0.8
                                        4    0.75-1.25  wp 50%                    0.7            1.3                           1.1            0.8
                               1977     2    1.5        wp 50%                    0.4            0.3                           0.3            0.2
                                        4    1.5        wp 50%                    0.8            0.5                           0.6            0.2

    Outdoor       New
                  Zealand      1978     3    0.5        wp 50%     0.1            0.1            0.1                           0.04
                                             1.0        wp 50%     0.2            0.1            0.3                           0.2

    glasshouse    UK           1977     5    0.28       wp 50%     0.8            0.6            0.4                           0.7
                                             0.39       wp 50%     0.8            0.7            0.4                           0.5
                                             0.56       wp 50%     1.1            0.3            0.6                           0.6
                                             0.78       wp 50%     0.4            0.5            0.5                           0.6
                               1976     3    0.22       wp 50%                                   0.4
                                             0.39       wp 50%                                   0.7
                                             0.78       wp 50%                                   0.9
                                                                                                                                                

    TABLE 6.  (con't)
                                                                                                                                                

                                        Application                Residues (mg/kg)at intervals(days) after application
                                                                                                                                                
    Crop          Country      Year     No.  Rate     Formulation                          (Days)
                                             (kg          (%)      0/1            3/4            7/9            10/11          13/14          21
                                                                                                                                                

    Eggplant      France       1978     1    1          wp 50%                                                                 1.5
                                                                                                                                                

    1  Reference - Sumitomo 1981;
    2  day 2;
    3  21 days;
    4  23 days;
    5  35 days.

    TABLE 7.  Residues of procymidone resulting from supervised trials in field crops and oil seeds1
                                                                                                                                             

                                          Application                     Residues (mg/kg) at intervals (days) after application
                                                                                                                                             
    Crop           Country      Year      No.   Rate (kg
                                                a.i./ha    Formulation    3         6         9/10      14/15     19/22          28/31
                                                                                                                                             

    Potato         Japan        1977      4
      whole                                                                                                       0.08           0.05
      peeled                                                                                                      0.03           0.03
      peel                                                                                                        0.19           0.23
                                1977      4
      whole                                                                                                       0.02           0.03
      peeled                                                                                                      0.01           0.01
      peel                                                                                                        0.11           0.19

    Rice           Japan        1976      3     0.75
      unpolished                                                                                                  1.5            1.4
      polished                                                                                                    0.4            0.7
      straw                                                                                                       8.7            3.8(3.4-4.1)
                                                                                                                 (8.5-9.0)
                                1976      5     0.75
      unpolished                                                                                                  2.0
      polished                                                                                                    0.7
      straw                                                                                                      13.0
                                                                                                                (12.9-13.1)
                                1976      3     0.75
      unpolished                                                                                                  2.1            1.5
      polished                                                                                                    0.4
      straw                                                                                                       8.1
                                                                                                                 (7.8-8.5)       3.0
                                1976      5     0.75
      unpolished                                                                                                  2.3
      polished                                                                                                    0.5
      straw                                                                                                       8.7(8.6-8.7)
                                                                                                                                             

    TABLE 7.  (con't)
                                                                                                                                             

                                          Application                     Residues (mg/kg) at intervals (days) after application
                                                                                                                                             
    Crop           Country      Year      No.   Rate (kg
                                                a.i./ha    Formulation    0/1           3       8/9     14/15    20/22          24       37/41
                                                                                                                                             



    Sunflower      Hungary      1977      3     1          wp 50%
      seed                                                                                                      <0.1
      seed         Hungary      1977      3     1          wp 50%                                                3.3(2.4-3.8)
      seed                      1978      3     1.5        wp 50%         0.1           0.1
      seed                      1978      3     1          wp 50%         0.4                                    0.01
                                                                         (0.37-0.44)
    ( seed                      1979      1     0.5        wp 50%                                                                        0.02
    ( head                                                                1.1           0.38    0.39    0.03                    0.02
      seed                      1979      3     0.5        wp 50%                                                                        <0.2
      seed                      1979      1     1          wp 50%                                                                        0.05
                                                                                                                                             

    1  Reference - Sumitomo 1981.
             Residue trials on raspberries were carried out in Poland and the
    UK; the residues were less than 2 mg/kg on the day of the last
    spraying.

    Black currant

         Residues in black-currants were in the range 5.3 to 6.9 mg/kg 1
    to 3 days after the last of three applications at normal rates and
    declined to 3.0 to 4.2 mg/kg after 7 days.

    Vegetables

    Lettuce

         Supervised residue trials were carried out in Japan, France, the
    Federal Republic of Germany and The Netherlands in 1976 to 1980 on
    lettuce grown outdoors and in glasshouses in different seasons. The
    residues were generally less than 3 mg/kg 3 to 4 days after the last
    of 3 to 6 treatments, except in the trials carried out in France on
    glasshouse lettuce in which comparatively high residues were found.
    This may have been partly because (1) the whole crop was analysed
    without any trimming of the outer leaves that normally occurs and (2)
    the average weight of the lettuce heads sampled was relatively low.
    The residue data from France in 1977 and 1978 suggests that the
    dilution effects caused by growth of the plants accounts for the major
    part of the decrease in the residue on indoor lettuce.

    Legume vegetables

         Residue data were available on kidney beans (French beans) from
    France, The Netherlands, and New Zealand and on soybeans from Japan.
    Residues in kidney beans were generally less than 2 mg/kg, 1 day or
    more after the last of 2 to 6 applications of 0.5 to 1.0 kg
    procymidone/ha.

    Fruiting vegetables

         Residue data on cucumbers, eggplants, gherkins, melons, green
    peppers and tomatoes were available from France, Japan, The
    Netherlands, New Zealand and the United Kingdom. Most of the data were
    obtained on glasshouse crops.

         Procymidone levels in cucumbers were less than 2 mg/kg one day
    after treatment. In a trial in France in 1977 on eggplants at 1 kg
    a.i./ha, twice the normally recommended rate, the residue level was
    1.5 mg/kg 14 days after spraying. In green peppers grown under glass,
    procymidone residues were less than 4 mg/kg one day after application
    and generally below 1 mg/kg after 14 days.

         Procymidone levels in tomatoes were generally below 5 mg/kg
    immediately after application. The maximum residue was 4.9 mg/kg one
    day after treatment at 1.5 kg/ha (twice the normally recommended
    dosage).

    Root and tuber vegetables

         Residue trials on potatoes were carried out in Japan; the
    residues were less than 0.1 mg/kg 19 days after the last of 4
    applications at 0.5 kg/ha.

    Bulb vegetables

         Residue data on onions were obtained from Japan and The
    Netherlands. When procymidone was applied at rates up to 1 kg/ha, the
    residues in the bulbs did not exceed 1 mg/kg, regardless of the
    interval between the last application and harvest.

    Rice

         Residue data on rice were obtained from Japan. Procymidone levels
    in unhusked rice were in the range 1.4 to 2.3 mg/kg 21 to 28 days
    after treatment. Polishing reduced the residues to less than 1 mg/kg.

    Oil seeds

         Residue trials were conducted in Hungary on sunflower and the
    residues in sunflower seeds were generally less than 1 mg/kg, with one
    exception where a maximum residue of 3.8 mg/kg was found 20 days after
    the last of three applications at 1 kg/ha. In the latter case,
    paraquat was applied as a haulm killer shortly before harvest.

    FATE OF RESIDUES

    In processing

         The residue in wine made from grapes treated with procymidone was
    30 to 50% of the residue on the grapes at harvest. (See Table 8).
    Residues were further reduced on distilling wine. When wine containing
    procymidone residues at 0.8 mg/kg was used to produce brandy, the
    procymidone residues in the distillate were 0.07 to 0.35 mg/kg,
    average 0.18 mg/kg (9 samples).

    In plants

         The dissipation and metabolism of 14C-procymidone, labelled at
    the carbonyl group, was studied in bean and cucumber plants grown
    under glass. After foliar application to beans at the rate of 250 g
    per leaf, procymidone disappeared from the plants with a half-life of
    approximately 20 days. After 30 days, 40.2% of the applied
    radioactivity was recovered. It was shown by TLC analysis that 92% of

        TABLE 8.  Residue decrease during wine processing
                                                                                   

                                       Residue (mg/kg), mean and range
                             Number                                                
    Country       Year       of        On grapes
                             trials    at harvest      In must        In wine
                                                                                   

    Fed.Rep. of   1976/77    9         2.9(1.2-6.6)   1.7 (0.7-2.6)  0.9 (0.7-1.0)
    Germany

    Italy         1975/76    2         0.93 1.94      1.25
                             2         1.56 4.12      2.68
                                                                                   
    
         In an experiment carried out in Spain in 1976 the decrease in the
    residue during fermentation of the must was evaluated and samples were
    taken 15 and 40 days after grape pressing. Results are reports in
    Table 9.

    TABLE 9.  Residue of procymidone(mg/kg)mean residue and range
                                                                        

    On grape        Grape juice on    In must at intervals (days)
    at harvest      day of pressing   after pressing
                                                                        

                                          15              40

    3.5 (2.7-4.4)   3.6 (2.8-4.5)     3.0 (2.5-3.6)   2.7 (2.3-3.2)
    5.7 (4.0-6.8)   5.5 (4.0-6.8)     4.3 (3.8-4.8)   3.8 (3.6-4.0)
                                                                        

    the 14C recovered after 30 days was the parent compound. Two minor
    metabolites were detected, procymidone-NH-COOH and procymidone-CH2OH,
    which together accounted for about 1% of the 14C applied. These
    metabolites are also found in animals after the oral administration of
    procymidone. Only small amounts of the applied radiocarbon was
    translocated to other parts of the plant: the 14C residues in pods
    and seeds were 13 g/kg and 6 g/kg respectively after 30 days. The
    residue of procymidone remains mainly on the outside of the treated
    leaves and can be rinsed off with acetone. Thirty days after
    application, the distribution of the 14C, expressed as the percentage
    of the applied radioactivity, was as follows (Sumitomo 1981):

        Total recovered            40.2
    On and in treated leaves   39.1

    In surface wash                                        (procymidone             28.4
     (rinsed 3 times
     with acetone)             30.2                        (procymidone-NH-COOH     1.3
                                                           (others, unidentified    0.2

                               (procymidone                7.7
                               (procymidone-NH-COOH        0.1
    Extracted from treated     (
     leaves 8.1                (procymidone CH2OH          0.1
                               (4-OH-procymidone           0.1
                               (others, not identified     0.2

    Not extractable            0.8
    Total in shoots            1.0
    In pods and seeds          <0.1
    In roots                   <0.1
    
         After application of a liquid formulation of 14C-procymidone to
    mature cucumber leaves adjacent to fruits at a rate of 250 g
    procymidone per leaf, the 14C was hardly translocated to either
    leaves or fruits. After 23 days, approximately 64% of the applied
    radioactivity was recovered from the treated leaves. Unchanged
    procymidone (62%) and three metabolites, procymidone-NH-COOH,
    procymidone-CH2OH and 4' OH-procymidone, were found in the treated
    leaves, the metabolites accounting together for 0.4% of the applied
    14C (Sumitomo 1978).

         Procymidone added to the nutrient solution in which cucumber
    plants were growing was fairly rapidly taken up by the plant. The
    highest peak of radioactivity was reached 8 days after treatment, with
    a residue level of 3.4 mg/kg fresh weight, whereas the concentration
    in the shoots was much higher (20 to 30 mg/kg procymidone
    equivalents). The distribution of procymidone and its metabolites
    expressed as a percentage of the radioactivity applied is given in
    Table 10.

    In soil

         The degradation of 14C-procymidone was studied in four different
    soils under aerobic, anaerobic and sterilized conditions. After 12
    weeks of incubation, about 57% and 72% of the applied 14C was
    recovered as unchanged procymidone under aerobic and anaerobic
    conditions, respectively, whereas about 70 to 77% was recovered as
    unchanged procymidone from the sterilized soils. The major degradation
    products were procymidone-NH-COOH(2-(3,5-dichlorophenyl-carbamoyl)-
    1,2-dimethyl(cyclopropanecarboxylic acid) and CO2 (Sumitomo 1976).

        TABLE 10.  Distribution and characterization of radioactivity after treatment of cucumbers with
               radioactive procymidone
                                                                                                             

    Days after                                                Radioactivity (% of applied)
    treatment                     procymidone    procymidone    procymidone    procymidone    procymidone
                                                   NH-COOH        CH2OH          4'OH           3' Cl
                                                                                                             

    2         nutrient              86.1            4.3            1.0            <0.1            0.4
              solution

              roots                  3.5           <0.1            -               -             <0.1

              shoots                 2.4           <0.1            -              <0.1            -

              fruits                <0.1            -              -               -             <0.1

    8         nutrient              26.1            5.0            2.8             0.5            0.5
              solution

              roots                  4.2            0.2            -               -             <0.1

              shoots                37.9            0.2            -               0.2            -

              fruits                 2.0            -              -               -             <0.1

    24        nutrient              15.6            1.5           <0.1            <0.1           <0.1
              solution

              roots                  3.0            0.1            -               -             <0.1

              shoots                55.0            0.6            -               0.4            -

              fruits                 1.3            -              -               -             <0.1

                                                                                                             
    
         In another experiment three types of soil were treated with
    10.2 mg/kg 14C-procymidone, labelled in the carbonoyl groups and
    held under glass under aerobic and submerged conditions for 15 months.
    The half-life of procymidone was about 4 months under submerged
    conditions, depending on the soil moisture content. The rate of
    decline under 60% soil moisture content was more rapid than under 40%.
    After 15 months the levels of procymidone parent compound in Azuchi,
    Kodaira and Takarazuka soil were 1.93-3.16 mg/kg, 2.21-3.28mg/kg and
    2.49-3.67 mg/kg respectively. The volatile 14C gradually increased
    with time, amounting after 15 months of incubation to 16.9 to 39.9% of
    applied 14C in Azuchi, 11.9 to 19.9% in Kodaira and 21.3 to 33% in
    Takarazuka soil. The bound 14C also gradually increased with time to
    12.2 to 24.5%, 42.1 to 48.6% and 15.0 to 18.2% of the applied 14C in
    Azuchi, Kodaira and Takarazuka soils respectively after 9 to 12 months
    of incubation, but decreased thereafter. The differences in the
    proportion of bound residue are related to the organic matter content,
    which is much higher in the Kodaira soil (15.3%) than in the two other
    soils (2.5 to 2.7%). More than seven degradation products were
    detected. None of these exceeded 5% of the applied radioactivity in
    the soils held under aerobic conditions. Procymidone is hydroxylated
    at the methyl group and at the 4-phenyl position in soil. Also
    dichlorination and cleavage of one or both bonds of the cyclic imide
    linkage takes place, ultimately yielding CO2 (Sumitomo 1980).

         The leaching behaviour of procymidone was studied using 25 cm
    soil columns packed with different soil types. Air-dry soil, 30 g, was
    mixed with 10 mg/kg 14C-procymidone and placed on top of the column
    immediately after mixing or after an incubation period of 4 weeks. The
    soil columns were leached with 550 ml water at a rate of 3 ml/h for 7
    weeks. The radiocarbon penetrated below 0 to 15 cm layers in the
    Kodairi, Azuchi and Takarazuka soils, all of which had an organic
    matter content of 2.5% or slightly higher. The eluate contained less
    than 3% of the applied 14C. However, in a very light Gifu soil with
    an organic matter content below 1%, the radiocarbon in the eluate
    amounted to 75.4% of the applied 14C.

         Incubation of the treated soil for 4 weeks resulted in a lower
    proportion of the 14C leaching through the soil columns. The
    radiocarbon in the leachate of a Gifu soil column was decreased to
    17.3% of that applied (Sumitomo 1980).

         Adsorption and desorption of 14C-procymidone was studied in
    aqueous soil suspension systems. Among 11 soil characteristics
    measured, the organic matter content was found to be the only factor
    that significantly affected procymidone adsorption. A good linear
    relationship in logarithmic expression was observed between
    procymidone adsorption and organic matter content in soils. The
    adsorption behaviour of procymidone is well described by the so-called
    Freundlich isotherms: the Freundlich k value varied from 1.1 to 6.0

    and the l/n value was close to one. The desorption isotherms exhibited
    hysteresis, apparent irreversibility, in comparison with adsorption
    isotherms (Sumitomo 1980).

    Residue uptake in plants from treated soils

         Bean seedlings were grown on two soils, incubated with 10 mg/kg
    of 14C-procymidone for two weeks and 5 months respectively for 42
    days. After 42 days, pods, seeds, shoots and roots were analysed for
    14C. The highest 14C levels in beans grown in Kodaira and Takarazuka
    soils incubated for two weeks were in the shoots 12.3 mg/kg and
    15.3 mg/kg procymidone equivalents respectively, whereas the 14C
    residue levels in the edible portions were 0.42 and 0.66 mg/kg.

         When beans were transplanted into soils incubated for 5 months
    with procymidone, the 14C residues in the shoots, pods and seeds were
    lower than in the beans grown after the shorter incubation period
    mentioned above. After 42 days the residue levels in the shoots were
    3.92 and 4.46 mg/kg and in the pods and seeds 0.12 and 0.25 mg/kg (the
    higher figures were in beans from Takarazuka soil) (Sumitomo 1981).

    Photodegradation

         Photodegradation of 14C-procymidone was studied in various
    solutions exposed to sunlight under glasshouse conditions. The half-
    lives of procymidone in distilled water, natural river-water and sea-
    water were 10, 1.0 and 0.6 days respectively. The degradation of
    procymidone in water exposed to sunlight seemed to be largely due to
    hydrolytic reactions, with sunlight showing a slight but definite
    effect on the breakdown. Procymidone was degraded via cleavage of the
    cyclic imide and further cleavage of the resulting amide linkage
    (Sumitomo 1980).

    Hydrolysis

         The hydrolysis of 14C-procymidone was studied in buffer
    solutions with pH ranges from 2 to 10 and in natural river and sea
    water at 15, 30 and 45 C. Procymidone is easily hydrolysed at pH
    6.3 and above at 45, at pH 7.1 and above at 30 and at pH 8 and above
    at 15. Half-life periods ranging from 30 min. to 8.1 days were found
    under these conditions. On the other hand, the compound is fairly
    stable at pH 2 and half-lives of 34 days (at 45C) to 62 days
    (at 15C) were found. The hydrolysis of procymidone proceeded
    predominantly through neutral (PH-independent) and base-catalysed
    processes in the regions below pH 5 and above pH 8 respectively, while
    both reactions occurred in the range between pH 5 and 8. In alkaline
    solutions, the degradation product formed by the cleavage of the
    cyclic imide was predominant, whereas the resulting amide was cleaved
    further to yield the main product under aerobic conditions (Sumitomo
    1980).

         In the light of the above data, the degradation pathways for
    procymidone in plants, water, soil and micro-organisms shown in Figure
    2 can be proposed.

    METHODS OF RESIDUE ANALYSIS

         The residue determination of procymidone parent compound is
    almost exclusively carried out by gas chromatography with electron
    capture detection (GC-ECD). The limit of determination in most plant
    material is as low as 0.2 ng or even less (Sumitomo 1976, 1978), which
    enables a limit of determination of 0.04 to 0.02 mg/kg in most cases
    (Sumitomo 1976,1978). The GC-ECD method is suitable or can be adapted
    for regulatory purposes.

         Capillary gas chromatography with a flame ionization detector
    also provided high sensitivity; the limit of determination was about
    0.05 ng, which enabled a limit of determination of procymidone as low
    as 0.01 mg/kg (Sumitomo 1978).

         Although the alkali flame ionization detector (AFID) in the
    nitrogen mode may also be used for residue analysis of procymidone, it
    appears that its response to procymidone was about one tenth of that
    of the ECD (Sumitomo 1980).

         The identity of procymidone residues can be confirmed by combined
    gas chromatography-mass spectrometry (GC-MS), using selected ion
    monitoring, giving 0.2 ng as a minimum detectable amount when m/e 283
    and m/e 285 are monitored (Sumitomo 1980).

         High-performance liquid chromatography (HPLC) with UV detection
    at 254 nm permits a limit of determination of 4 ng, which corresponds
    to about 0.05-0.01 mg/kg; however, the method has so far been used
    very little in residue analysis for procymidone.

    Extraction and clean-up procedures

         Procymidone was successfully extracted from substances with a
    relatively high moisture content (fruits, leafy vegetables and root
    crops) by chopping and blending with polar solvents such as acetone
    (Sumitomo 1978; Cooke  et al 1979), acetonitrile (Sumitomo 1978), or
    methanol-acetonitrile (Sumitomo 1976) or with non polar solvents, such
    as trimethylpentane (Sumitomo 1976) or hexane. Procymidone was
    preferably extracted from substrates with a low moisture content, such
    as rice or soybeans, by pulverising and macerating with acetonitrile
    (Sumitomo 1976, 1979).

         Clean-up procedures for extracts from oil-containing commodities,
    such as soybeans and rice, may be needed prior to further
    chromatographic separations, including partition between acetonitrile
    and n-hexane. Combined partition-Florisil column chromatography gave

    FIGURE 2

    recoveries of 83 to 87% for rice and soybeans spiked at 0.2 mg/kg of
    procymidone (Sumitomo 1976).

         For non-oily crops, clean-up was by chromatography on Florisil,
    alumina or mixed adsorbents containing active carbon, MgO and
    diatomaceous earth. Recoveries of 80% and above were achieved at
    fortification levels of 0.02 to 10 mg/kg for strawberries (Sumitomo
    1976, 1978), tomatoes (Sumitomo 1976), peaches (Sumitomo 1978),
    cucumber (Sumitomo 1976), grapes (Sumitomo 1976), lettuce (Sumitomo
    1978) and beans (Sumitomo 1976).

    NATIONAL MAXIMUM RESIDUE LIMITS

         The national maximum residue limits established or under
    consideration by May 1981 and the recommended pre-harvest intervals
    are given in Table 11.

    EVALUATION

         The data base for toxicological evaluation of this compound
    included several critical studies performed by Industrial Biotest
    Laboratories. In the absence of complete reports of validations for
    these studies that were essential to the estimation of an ADI, the
    Meeting was unable to accept the studies for evaluation and agreed to
    defer consideration of the toxicology this compound to a future
    meeting.

         Procymidone is a fungicide with a locally systemic action when
    applied to the aerial parts of plants. It shows, however, a marked
    systemic effect following applications to roots or the soil. It is
    effective for the control of some species of Ascomycetes and a few
    Deuteromycetes, especially  Botrytis spp., in fruits, vegetables,
    some field crops and oil seeds. It is marketed as a 50% wettable
    powder and a 500 g/l emulsifiable concentrate.

         On various crops, e.g. stone fruits (cherries, peaches) and berry
    fruits (grapes, strawberries and similar berries), procymidone is used
    until shortly before harvest to avoid fungal decay during transport
    and distribution. Residue data from supervised trials were available
    on 25 crops and from 12 countries (Japan, Australia, New Zealand and
    Europe), representing a wide range of climatic conditions and
    agricultural practices. Extensive information was available on the
    fate of procymidone in plants, in soil (including metabolism in micro-
    organisms), in water, under UV irradiation, etc.

         In most cases, the residue on or in plants consists mainly of the
    parent compound, often 90 to 95% or more. The main degradation pathway
    is hydroxylation at the methyl group and the 4 position of the phenyl
    group, followed by cleavage of the cyclic imide. The two major
    metabolites are procymidone-CH2OH and procymidone-NH.COOH, but these

        TABLE 11.  National maximum residue limits reported to the Meeting
                                                                                                              

    Country             Commodity                               MRL (mg/kg)       Pre-harvest intervals (days)
                                                                                                              

    Australia           stone fruits                               10                        1
    Czechosslovakia     grapes                                                              28
    France              grapes                                      5
                        beans, chicory leaves,                      5
                        lettuce

    Fred. Rep.of
    Germany             grapes                                                              28

    Hungary             berries, cherries
                        (sour)                                      3                       14
                        grapes                                      3                       14
                        sunflower seed                              3                       21
                        wine                                        3

    Japan               fruits                                      3
                        peaches                                                             14
                        strawberries                                                         3

                        vegetables (except potatoes)                2
                        beans (kidney),celery                                               14
                        beans (azuki, soy)                                                  21
                        lettuce                                                              7
                        onion                                                                1

                        cucumber, eggplant                                                   1
                        sweet pepper                                                         7
                        tomato                                                               3

                        potato                                      0.2                     21
                                                                                                              

    TABLE 11.  (con't)
                                                                                                              

    Country             Commodity                               MRL (mg/kg)       Pre-harvest intervals (days)
                                                                                                              

    Netherlands         strawberries                                3                       14
                        beans, endive, lettuce                      1                       14
                        vegetables (cucumber, courgette,
                        eggplant, gherkin,melon,sweet
                        pepper, tomato)                             1                        3

                        onions, shallots                            0.2                     14

    New Zealand         grapes                                      5                        1
                        stone fruits                                3                        1
                        kiwi fruit                                  7                        3
                        strawberries                                0.5                      1
                        beans                                       2                        3
                        lettuce, tomato                             1                        3

    South Africa        grapes (table grapes)                       1                        7

    Yugoslavia          grapes                                                              28
                                                                                                              
        usually amount to only a low percentage of the total plant residue.
    They are also found in animals after oral administration.

         Several analytical methods are available for the residue in
    crops, soil, water and animal tissues. Gas chromatography with
    electron capture detection is the method of choice and is suitable or
    can be adapted for regulatory purposes. The lower limit of
    determination for most samples is in the range of 0.004 to 0.02 mg/kg.

    RECOMMENDATIONS OF RESIDUE LIMITS

         From the data available the meeting estimated the maximum residue
    levels that were likely to occur on various food commodities after the
    use of procymidone in accordance with present good agricultural
    practice. These levels were considered suitable for establishing
    guideline levels. The data presented on residues in chicory (witloof)
    were not sufficient to allow guideline levels to be proposed. The
    levels refer to procymidone only.

                                                                        
    Crop                          GL (mg/kg)   Pre-harvest interval (days)
                                                                        
    Apples                            5                 7
    Cherries                          5               1-3
    Currants (black, red,white)      10                 7
    Grapes                            5                21
    Kiwi fruit                        7                 7
    Nectarines                       10               1-7
    Peaches                          10               1-7

    Raspberries                       5                 7
    Strawberries                     10                 7 outdoors
                                                       14 glasshouse

    Beans, kidney                     2                14

    Lettuce                           5                21
    Onions                            0.2              21
    Potatoes                          0.1              21

    Cucumbers                         2                 3
    Eggplant                          2                 3
    Gherkins                          2                 3
    Melons                            1                 3
    Peppers                           5                 3
    Tomatoes                          5                 3

    Rice husked                       3                21
         polished                     1                 -
    Sunflower seed                    2                21
                                                                        

    FURTHER WORK OR INFORMATION

    Desirable:

    1.   Information on residues from supervised trials on additional
         crops on which use is recommended, e.g. soybean, plum, chicory
         (witloof).

    2.   Information on residues in products of animal origin arising from
         feeding wastes of treated crops, e.g. sunflower cake, potatoes,
         pea and bean vines, feed potatoes, etc.

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    See Also:
       Toxicological Abbreviations
       Procymidone (Pesticide residues in food: 1989 evaluations Part II Toxicology)