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 formulaOther 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 25°C Solubility Acetone 18.0, acetonitrile 10.1, (% w/w at 25°C) cyclohexanone 14.8, ethyl acetate 11.5, methanol 1.6, xylene 4.3 Solubility in water 4.5 mg/l at 25°C 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 60°C. 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 µg 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 µg/kg and 6 µg/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 µg 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 45°C) to 62 days (at 15°C) 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
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. REFERENCES Altman, P.L. and Dittmer, D.S. (Eds.) Biology Data Book Second 1974 Edition, Volume 3, Federation of American Societies for experimental Biology, Bethesda, USA, p.272. Arai, M. Hasegawa, R. and Ito, N. Three-month sub-acute toxicity study 1980a of S7131 (SumilexR, SumisclexR) in mice. Report from Department of Pathology, Medical Technology and Nursing, Fujita Gakuen University, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) 1980b Six-month subacute toxicity study of S7131 (SumilexR, SumisclexR) in mice. Report from Department of Pathology, School of Medical Technology and Nursing, Fujita Gakuen University, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Arai, M., Tatematsu, M., Hagiwara, A., Hirose, M., Muraskai, G., 1981a Murakami, M. Ito, S. and Ito, N. Eighteen-month chronic toxicity and carcinogenicity study of S7131 (SumilexR, SumisclexR) in Swiss white mice. Report from Department of Pathology, School of Medical Technology and Nursing, Fujita Gakuen University, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Arai, N., Tatematsu, M., Nakaniski, K., Hirose, M., Miyata, S., 1981b Hiromori, T., Okuno, Y. and Ito, N. Two-year chronic toxicity study of S7131 in rats. Report from Department of Pathology, School of Medical Technology and Nursing, Fujita Gakuen University, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Carlson, D.S., Burtner, B.R., Kennedy, G.L., Kinoshita, F.D. and 1977 Keplinger, M.L. 90-day sub-acute oral toxicity study with S-7131 technical in beagle dogs. IBT No. 9531-09232. Report from Industrial Bio-Test Laboratories, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Cooke, B.K, Pappas, A.C., Jordan, R.W.L. and Western, N.M. 1979 Translocation of benomyl, Prodyloraz and procymidone in relation to control of Botrytis cinerea in strawberries. Pesticide Science, 10:467-472. Fletcher, D., Jenkins, D.H., Kinoshita, F.K. and Keplinger, M.L. undated 12-week subacute oral toxicity study with S7131 in albino mice. IBT No. 651-06728. Report from Industrial Bio-Test Laboratories, submitted by Sumitomo Chemical Co. Ltd., Japan. (Unpublished) Hara, M., Suzuki, H. and Ohkawa, H. Cytogenetic test of procymidone in 1980a mouse bone marrow. Report from Research Department, Pesticide Division, Sumitomo Chemical Co. Ltd. submitted by Sumitomo Chemical Co. Ltd., Japan. (Unpublished) Hara, S., Suzuki, T. and Miyamoto, J. Skin sensitization test of S7131 1980a 50% water dispersible powder in male guinea pigs. Report from Research Department, Pesticide Division, Sumitomo Chemical Co., Ltd., submitted by Sumitomo Chemical Co. Ltd., Japan. (Unpublished) Hishada, Y., Maeda, K., Kawase, Y. and Miyamoto J. Uptake and 1976 translocation of a systemic fungicide, S7131 in cucumber plants. Journal of Pesticide Science, 1:201-206. Hishada, Y., Maeda, K., Tottori, N., and Kawase, Y. Plant 1976 disease control by N-(3',5'-dichlorophenyl)- 1.2-dimethylcyclopropane-1,2-dicarboximide. Journal of Pesticide Science, 1:145-149. Kadota, K. and Miyamoto, J. Eye and skin irritation study with S7131 1976 technical material in albino rabbits. Report from Institute for Biological Science, Hyogo, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Kadota, T., Kohda, H. and Miyamoto, J. Acute toxicity studies with 1976 S7131 technicam material in mice and rats. Routes of administration - oral, subcutaneous, intraperitoneal and dermal. Report from Institute for Biological Science, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Kato, T., Fujita, T. and Fukuda, T. Toxicity of S7131 technical 1976 material to rats in prolonged dietary administration over nine months. Report from Research and Development Center, Hyogo, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Kohda, H. and Kadota, T. Acute oral and dermal toxicity studies with 1976a S7131 (Sumilex) 50% wettable powder in mice and rats. Report from Institute for Biological Science, Hyogo, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) 1976b Acute inhalation toxicity of Sumilex 50% wettable powder in rats, Report from Institute for Biological Science, Hyogo, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Kohda, H., Nakamura, M., Kadota, T. and Miyamoto, J. Acute oral and 1980 subcutaneous toxicity studies of three metabolites of procymidone. Report from Research Department, Pesticide Division, Sumitomo Chemical Co. Ltd. submitted by Sumitomo Chemical Co. Ltd., Japan.(Unpublished) Ladd, R., Smith, P.S., Jenkins, D.H., Kennedy, G.Jr., Kinoshita, F.K. 1976 and Keplinger, M.L. Teratogenic study with S7131 in albino rabbits. IBT No. 651-06730. Report from Industrial Bio-Test Laboratories, Inc., submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Matsubara, T., Hara, S., Suzuki, T. and Kadota, T. Primary eye and 1979 skin irritation tests of S7131 50% water dispersible powder in rabbits. Report from Research Department Pesticides Division, Sumitomo Chemical Co. Ltd., submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Mikami, N., Satogami, H. and Miyamoto, J. Metabolism of procymidone in 1979 rats. Journal of Pesticide Science, 4:165-174. Moriya, M. Kato, K. and Shirasu, Y. Mutagenicity of S7131 in bacterial 1977 test systems. Report from Research Department, Pesticide Division, Sumitomo Chemical Co. Ltd., submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Okuno, Y., Kadota, T. and Miyamoto, J. Skin sensitization study with 1975 S7131 in guinea pigs. Report from Research Department, Pesticides Division, Sumitomo Chemical Co. Ltd., submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Pence, D.H., Hoberman, A.M,, Durloo, R.S., Andrews, J.P. and Monsburg, 1980 P.A. Teratology study in rats S7131(technical). Report from Hazleton Laboratories Inc., USA, submitted by Sumitomo Chemical Co. Ltd. (Unpublished). Principe, P., Monaco, M. and Nunziata, A. Report on mutagenicity 1980 experiment on the substance Sumisclex (procymidone) of the firm Sumitomo Chemical Co. Ltd. of Hyogo (Japan). Report from Centro Ricerca Farmaceutica, S.p.A. Italy, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Salamon, C., Smith, S., Arnold, D.W. and Mannear, J.H. Three 1978 generation reproduction study with S7131 in albino rats. IBT No. 623-06729. Report from Industrial Bio-Test Laboratories Inc., submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Segawa, T. Acute intraperitoneal toxicity of S7131 50% water 1979 dispersible powder in mice. Report from Department of Pharmacology, Institute of Pharmaceutical Science, Hiroshima University School of Medicine, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Segawa, T. Acute oral, subcutaneous, intraperitoneal and dermal 1981 toxicities of S7131 in rats and mice. Report from Department of Pharmacology, Institute of Pharmaceutical Science, Hiroshima University, School of Medicine, submitted by Sumitomo Chemical Co. Ltd. (Unpublished) Sumitomo. Reports submitted to FAO by Sumitomo Chemical Co. Ltd., 1976,1978 Osaka, Japan. (Unpublished) 1980,1981 Suzuki, H. and Miyamoto, J. Studies on mutagenicity of S7131 with 1976 bacterial systems. Report from Institute for Biological Sciences, Hyogo, Japan, submitted by Sumitomo Chemical Co. Ltd, (Unpublished) Suzuki, H. and Ohkawa, H. Effects of procymidone on sister chromatid 1980 exchanges (SCE) in cultured mouse embryo cells. Report from Research Department, Pesticide Division, Sumitomo Chemical Co. Ltd., Hyogo, Japan. (Unpublished) Tatematsu, M., Tatatsuka, M. and Arai, M. Two-year toxicity study of 1981 SumilexR (S7131) in beagle dogs. Report from First Department of Pathology, Nagoya City University Medical School, Nagoya, Japan, submitted by Sumitomo Chemical Co. Ltd. (Unpublished)
See Also: Toxicological Abbreviations Procymidone (Pesticide residues in food: 1989 evaluations Part II Toxicology)