PESTICIDE RESIDUES IN FOOD - 1979 Sponsored jointly by FAO and WHO EVALUATIONS 1979 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, 3-12 December 1979 DICHLOFLUANID Explanation Dichlofluanid was evaluated at the meetings in 1969, 1974 and 1977. In 1977 when the temporary ADI was extended, further data were required on (1) studies to elucidate the accumulation seen in the thyroid and (2) results from current studies on the pathways of degradation, especially the fate of the fluorine-containing moiety of the molecule in or on plants. In addition, further information concerning residues, especially residues on melons and leaf brassicas were considered to be desirable. At the 1979 Session of the CCPR, a number of questions were raised concerning the MRLs proposed for blackberries, gooseberries, eggplant and onions. The monograph addendum reviews the additional information received. EVALUATION FOR ACCEPTABLE DAILY INTAKE Biochemical Aspects Rats were dosed with 5 and 10 mg 14C-dichlofluanid/kg/body weight by oral and intravenous routes. Forty to fifty percent of the dose was excreted in the urine within 8 hours after application. The main radioactive metabolite in urine was identified as thiazolidin-2-thio-carbonic acid (TTC). Eight hours after intravenous administration of 5 mg 14C-dichlofluanid/kg body weight, 74 to 92% of the urinary radioactivity was identified at TTC. After oral administration, TTC was noted to range from 57 to 64% of the radioactivity in urine. The remaining radioactivity was distributed among several other minor metabolites. The parent compound was not identified in urine (Ecker, 1978). TOXICOLOGICAL STUDIES Signs of poisoning included apathy and dyspnea. Sedation was observed in mice at high doses. Post-mortem examination revealed pale and marble-like kidneys, pale and spotted liver, empty and reddish stomach, and intestine with erosion and decomposition of the gastric, glandular mucosa (Flucke, 1978). The acute oral LD50 for male rats of thiazolidin-2-thio-carbonic acid (TTC) the main urinary metabolite of dichlofluanid, is greater than 1000 mg/kg body weight (Thyssen, 1978). Table 1. Acute Toxicity of Dichlofuanid to Various Animals LD50 Animal Sex Route (mg/kg/b.w.) Reference Rat M Oral >5000 Flucke, 1978 Rat M&F Oral >5000 Flucke, 1978 Mouse M Oral 5464 Flucke, 1978 Mouse F Oral 5597 Flucke, 1978 Guinea pig F Oral 945 Flucke, 1978 Rabbit F oral approx. 3500 Flucke, 1978 Cat F Oral >1000 Flucke, 1978 Rat M&F Dermal (24 hr exposure) >5000 Flucke, 1978 Special Studies on Mutagenesis The Micronucleus test was carried out in male and female mice for possible mutagenic action on chromosomes of erythroblasts in bone marrow. Two oral doses were given within 24 hours (2 × 1000 and 2 × 2000 mg dichlofluanid/kg/body weight). Endoxan (cyclophosphamide) (2 × 100 mg/kg body weight) was administered as positive control. This test did not indicate any mutagenic action of dichlofluanid (Herbold, 1978). An "Ames test" was performed to evaluate a possible point mutation activity of dichlofluanid. Salmonella typhimurium TA-1535, TA 1537, TA-98 and TA100 strains were used in the tests at doses of 4, 20, 100, 500 and 2500 µg/plate. Endoxan (500 µg cyclophosphamid/plate) and trypoflavin (250 µg/plate) were used as positive controls. An S-9 microsomal activation system was used with all test doses. A mutagenic effect of dichlofluanid was observed only with Salmonella typhimurium TA-100 at the 200 µg/plate dose. Higher doses were toxic to the bacteria. These experiments were repeated with the following test doses: 0, 50, 100, 200 and 400 µg/plate. A mutagenic effect was observed in the 100 and 200 µg/plate doses with TA-100. The 400 µg/plate dose was again toxic. No mutagenic effects were observed with the TA-1535, TA 1537 or TA-98 strains. Dichlofluanid was mutagenic in the "Ames test" only with the TA-100 strain (Herbold, 1979a). Cytogenetic studies in the Chinese hamster spermatogonia were carried out with dichlofluanid given orally to male animals in two daily doses (2 × 250 and 2 × 500 mg/kg body weight). The animals presented no clinical signs of poisoning, although one animal at the high dose died. The positive control group received Adriblastin (doxorubicin) 2 × 5 mg/kg body weight by intraperitoneal injection. No differences were observed between the negative control and the dichlofluanid-treated animals. Differences between the negative and positive control groups were highly significant (Herbold, 1979b). A dominant lethal study was carried out in mice. Groups of 20 male (NMRI) mice received a single oral dose of 0 or 500 mg dichlofluanid per kg body weight. After administration, each male was mated with 3 untreated females, every week, for eight consecutive weeks. The females were sacrificed on day 14 of gestation. Pre-implantation and post-implantation losses were calculated from the number of corpora lutea, the number of implantations and the number of living and dead embryos. Dichlofluanid treatment did not have any harmful effects on the males, did not impair their mating performance, and did not affect fertility. Post-implantation data did not suggest any mutagenic action of dichlofluanid. A significant pre-implantation loss was, however, observed in the second mating week (Machemer, 1974a). Special Studies on Embryotoxic and Teratogenic Effects Embryotoxicity and teratogenicity studies were carried out in rats following oral administration of dichlofluanid at daily doses of 0, 30, 100 and 300 mg/kg body weight from day 6 to day 15 of gestation. On day 20, the foetuses were removed from the dams by Caesarian section and examined for visceral and skeletal malformations. All test doses were slightly toxic to the dams. Several animals showed acute poisoning signs (diarrhea, ruffled coat, dyspnea, inactivity, and loss of body weight). There was no overt mortality in the study. This study revealed: (1) dichlofluanid was toxic by the oral route to pregnant dams at 30 mg/kg body weight/day and above; (2) a significant increase in the number of foetuses with malformations (P <0.05) was observed at the dose level of 100 mg/kg/day (the highest dose (300 mg/kg/day) did not reveal an equivalent increase); and (3) a no effect level for foetal development was 100 mg/kg/day (Machemer, 1974b). Short-Term Studies The threshold dose of dichlofluanid was stated to be 5.4 mg/kg observed in a 10-month experiment reported to the meeting in abstract only (Belonozhkol, et al., 1978). A review of the original data was not made and was considered to be necessary before the data can be fully evaluated. COMMENTS Dichlofluanid was evaluated for an acceptable daily intake by the meeting in 1969, 1974 and 1977. A temporary ADI was established in 1974 JMPR and extended at the same level in 1977. Several tests for mutagenicity (micronucleus, cytogenetic, dominant lethal, and microbial tests) were essentially negative. However, a positive response was obtained in one bacterial strain in the "Ames assay". The studies required by the 1977 JMPR on the effects of the possible accumulation in the thyroid are known to be in progress. The meeting extended the temporary ADI to allow these studies to be completed. TOXICOLOGICAL EVALUATION Level Causing No Toxicological Effect Rat: 1500 ppm in the diet, equivalent to 75 mg/kg body weight Dog: 1000 ppm in the diet, equivalent to 25 mg/kg body weight ESTIMATE OF TEMPORARY ACCEPTABLE DAILY INTAKE FOR MAN 0 - 0.3 mg/kg body weight. RESIDUES IN FOOD AND THEIR EVALUATION USE PATTERN Pre-harvest treatment Information from the manufacturer (Bayer, 1979a) stated that they are not recommending the use of dichlofluanid on melons and leaf brassicas and therefore would not be supplying data for these crops. RESIDUES RESULTING FROM SUPERVISED TRIALS Information supplied by Bayer AG (Bayer, 1979a) reported that until 1978 when a new ordinance was issued requiring the determination of the parent only, legislation in the Federal Republic of Germany had required the determination of the sum of dichlofluanid plus the metabolite dimethyl aminosulfanilide (DMSA). Therefore, the great majority of their existing residue data was expressed as the combined residue with no possibility of differentiation between the two components. As a result, the residues data compiled in the Table on pages 127 and 128 of the 1977 Evaluations and referring to Bayer Reports (coded country D) are invalid for reflecting the true residue situation and should be deleted, except for the potato results which were below detectable limits anyway. The Nitokuno values in 1977 from Japan (coded country J) are correct and should be retained. These include cucumber, eggplant, hops, lettuce, onion bulbs, strawberries under glass, and tomatoes. In view of the widespread use of dichlofluanid and the large number of national MRLs already established (based mainly on parent compound alone), it is proposed to retain the other MRLs proposed in 1977 on a temporary basis and until such time as acceptable data from new field trials becomes available, including data supplied to this meeting. Additional residue data were received from supervised trials conducted in Japan and Finland and are summarized in Table 2. Table 2. Residues of dichlofluanid in fruits and vegetables from supervised trials Dose, No. of Days after Residues Reference Crop Country kg a.i./ha applications last application mg/kg Apple Finland 0.004 kg/ 3 62 <0.005 peeled State Inst. Agri. tree <0.005 washed Chem., 1967 0.05 unwashed 4 14 1.5 peeled 4.0 washed 3.2 unwashed Finland 5 g/tree 1 14 6.9 unwashed State Inst. Agri. Chem., 1973 Black Finland 3.75 g/bush 2 56 0.5 unwashed State Inst. currant 3 38 1.0 unwashed Agri. Chem., 1972 Finland 3.75 g/bush 2 57 0.4 unwashed State Inst. 3 49 3.0 unwashed Agri. Chem., 1973 Cucumber Japan 0.08g/m3 0 - ) (steam fog) 1 1 ) 3 ) 7 ) all <0.006 Nitokuno, 1972 2 1 ) 3 ) 7 ) Cucumber Japan 2 0 - <0.003 Nitokuno, 1973 (greenhouse) (drench) 3 3 0.007 7 0.004 14 0.005-0.007 5 3 0.003-0.011 7 0.005-0.009 14 0.005-0.009 Table 2. Continued... Dose, No. of Days after Residues Reference Crop Country kg a.i./ha applications last application mg/kg Cucumber Japan 0.08g/m3 0 - ) (greenhouse) (steam fog) 2 1 ) 3 ) 7 ) All <0.01 Nitokuno, 19761 3 1 ) 3 ) 7 ) Cucumber Japan 30 0 - <0.01, 0.01 Nitokuno, 19761 (drench) 1 3 <0.01, 0.01 7 0.14, 0.19 3 3 0.04, 0.11 7 0.03, 0.05 Gooseberry Finland 3.75 g/bush 2 41 2.6 unwashed State Inst. Agri. 3 29 2.8 unwashed Chem., 1972 Hop Japan 31.25 2 46 0.27 Nitokuno, 1977 (spray) 3 37 0.28 3 34-36 0.10 Strawberry Japan 0.04 g/m3 0 - <0.004, <0.004 Nitokuno, 19731 (greenhouse) steam fog) 1 1 0.023, 0.021 3 0.012, 0.010 7 0.006, 0.012 2 1 0.040, 0.020 3 0.011, 0.014 7 0.008, 0.010 Table 2. Continued... Dose, No. of Days after Residues Reference Crop Country kg a.i./ha applications last application mg/kg Strawberry Japan 24.9 0 - <0.01, <0.005 Nitokuno, 1975 (drench) 6 1 0.24, 0.166 plus 3 0.10, 0.246 2 7 0.06, 0.082 spray 8 1 0.12, 0.178 3 0.08, 0.278 7 0.03, 0.071 Strawberry Japan 24.9 0 - <0.01, 0.006 Nitokuno,19751 (greenhouse) (drench) 6 1 0.27, 0.292 plus 4 0.08, 0.114 7 7 0.18, 0.234 (spray) 8 1 0.10, 0.266 4 0.10, 0.146 7 0.20, 0.409 Strawberry Finland 0.25 kg/ 3 19 0.2 washed State Inst. Agri. line meter 0.6 unwashed Chem., 1967 11 g/a 3 19 0.15 washed 0.5 unwashed 0.25 kg/ 2 26 0.02 washed line meter 0.4 unwashed 11 g/a 2 26 0.01 washed 0.01 unwashed Finland 0.25 kg/ 3 14 0.03 washed State Inst. Agri. line meter 0.07 unwashed Chem., 1968 2 26 0.03 washed <0.03 unwashed Finland 25 g/a 3 8 18 unwashed State Inst. Agri. 2 15 1.5 unwashed Chem., 1971 Table 2. Continued... Dose, No. of Days after Residues Reference Crop Country kg a.i./ha applications last application mg/kg Tomato Japan 0.08 g/m3 0 - <0.004 Nitokuno, 1972 (greenhouse) (steam fog) 1 1 0.005 3 <0.004 7 <0.004 2 1 0.014 3 <0.004 7 <0.004 Japan 0.08 g/m3 0 - <0.01, <0.01 Nitokuno, 19761 steam fog 2 1 0.02, <0.01 3 <0.01, <0.01 7 <0.01, <0.01 3 1 <0.01, <0.01 3 0.01, <0.01 7 <0.01, <0.01 Watermelon Japan 30 0 - <0.01, <0.01 Nitokuno, 19761 (drench) 5 7 <0.01, <0.01 6 7 <0.01, <0.01 1 Samples analysed by two different institutes. FATE OF RESIDUES In plants Dichlofluanid labelled with 14C in the dichlorofluoromethyl position was sprayed on wine grapes 35 days before harvest time (Voleler et al., 1979). At harvest only 29% of the applied radioactivity could be detected while 71% had vaporised. Of the remaining radioactivity in the grapes, 91% was in the form of unchanged starting material. A methanol extract of the grapes contained small quantities (2.2% and 5.3%) of two unidentified metabolites. During wine making, 23% of the radioactivity in the grapes went over into the wine, 70% remained in the residue (must), and 6% was evolved with the CO2 given off. Of the radioactivity in the wine, 70-80% was identified at the metabolite thiazolidine-2-thione-4-carboxylic acid (TTCA) arising from the reaction between thiophosgene and cystein. The content of TTCA in wine was around 0.1 mg/l. The degradation and metabolism of 14C-dichlofluanid (dichlorofluoromethyl position labelled) in strawberries was studied by Westphal, et al. (Westphall et al, 1979). Strawberry plants grown in a closed, air flow controlled glass cultivating system were sprayed with an aqueous preparation of the 14C-50% wettable powder at the end of the flowering period and cultivated in the closed system until harvest (36 days). Strawberries, leaves, roots and soil contained 8%, 71%, 3% and 5% respectively, of the originally-applied radioactivity, while 6% 14C-CO2 was released along with traced of carbonyl sulphide. Small amounts of radioactivity were found in the condensed and percolated water of the system. Results are tabulated as follows: Table 3. Distribution of 14C-dichlofluanid metabolites in strawberry culture system Extractable radioactivity, % Less polar Polar bound Dichlofluanid TTCA metabolite (5) metabolite (5) radioactivity Strawberries - 1.3 6.3 37.3 55.1 leaves 38.6 7.0 - 24.6 29.8 soil - - 2.7 12.3 85.0 (upper 5 cm) From this experiment, it is concluded that the dichlorofluororomethylmercapto moiety of the parent compound is easily cleaved off, leading to unstable intermediates such as sulfinic acid and thiphosgene or its fluoro analogue. This mechanism is supported by the detection and identification of carbonyl sulphide, a hydrolysis product of thiophosgene and TTCA, a reaction product of thiophosgene and naturally-occurring cysteine. Eventually the chlorine and fluorine atoms are released as inorganic ions. Similar results and conclusions were obtained for an experiment using 14C-tolylfluanid although more undegraded parent compound was found in strawberries in this case (Haque, et al., 1979). The metabolic pathway for either dichlofluanid or tolylfluanid is shown in Figure 1. The metabolism of the tolyl analogue of dichlofluanid, tolylfluanid, was determined on apples growing on small trees growing in a greenhouse (Vonk, et al., 1977). After 28 days post-treatment, approximately 42% of the originally applied-radioactivity (as dichlorofluoromethyl-14C, tolylfluanid spray) had disappeared probably as volatile compounds, ca. 41% was due to unchanged starting material, and ca. 17% was unidentified material. In soil Information on the rate and extent of the degradation of 14C-dichlofluanid (labelled in the dichlofluoromethylthio carbon) in soil was provided in a report on an experiment utilizing two soil types, a high humus sandy loam (soil I) and a medium humus sandy loam (soil II), incubated in biometric flasks fitted with side-arm chambers containing 0.1 N KOH (Schuphan, et al., 1979a). The results are summarised in Table 4. Similar results were obtained for 14C-tolylfluanid (Schuphan, et al., 1979b). Additional information on soil degradation was provided in Table 2. Table 4. Degradation of 14C-dichlofluanid in soils Time after Total 14CO2 Extractable 14C- start of evolved, % remaining, % experiment, days soil I Soil II Soil I Soil II 3 45.0 36.4 4.7 57.0 7 61.5 57.2 1.3 (5.3) 14 69.5 77.1 0.92 20.4 31 74.0 92.7 0.52 1.7 63 77.5 98.5 0.36 0.80In storage and processing Strawberries treated in a normal way with non-radioactive dichlofluanid to yield an analytically determined residue of 5.9 mg/kg parent compound (I) and 1.6 mg/kg of the metabolite dimethylaminosulfanilid (II) when harvested two days after treatment, were subjected to various processing steps to give unwashed raw berries, washed raw berries, canned fruits, pasteurized juice, and jam which were analysed to evaluate the effect on residues (Hartman, et al., 1979). Substantial reductions in residues were achieved by processing as shown in Table 5. Table 5. Concentration of active ingredient and metabolite on strawberries and processed products. Sample I, mg/kg II, mg/kg Berries, unwashed 5.9 1.6 Berries, washed 0.35 0.85 Wash water 1.95 0.2 Juice, raw 0.02 0.85 Juice, pasteurized N.D.1 0.9 Pomace 0.35 1.4 Canned fruits 0.02 0.75 Jam N.D. 1 0.4 1 N.D. = not detectable. Photodecomposition In studies carried out in England, the degradation of dichlofluanid by ultraviolet light was measured in methanol, benzene, and acetone solution (Clark et al., 1978). Solutions in methanol or benzene deposited a brown solid on the UV lamp surface (Hanovia, 100 W.) stopping the reaction. In acetone solution darkening occurred, but no solid separated, permitting a reaction time of one hour. Products from the acetone solution included N,N-dimethyl-N'-phenylsulfamide, phenyl isocyante, phenyl isothiocyanate, and dimethylamidosulfonyl chloride. The presence of bis (dichlorofluoromethyl) disulfide, 1-(dichlorofluoromethylthio) propan-2-one and 1-(dichlorofluoromethyl-sulfonyl) propan-2-one. In vivo tests against Botrytis einerea showed that irradiation decreased the activity of dichlofluanid and that synergism did not occur. EVIDENCE OF RESIDUES IN FOOD IN COMMERCE OR AT CONSUMPTION Information was supplied by Sweden on the results of analysing twenty samples of Swedish strawberries during 1979. No samples contained detectable levels of dichlofluanid (<0.03 mg/kg, Sweden, 1979). The results of monitoring surveys on several lots of produce imported into Finland during 1978 are shown in Table 6 (Finland, 1979). Table 6. Occurrence of residues of dichlofluanid in produce imported into Finland in 1978 Commodity No. of positive results Found (mg/kg) Cucumbers 6 0.01-0.28 Apples 1 0.06 Strawberries 2 <0.01, 0.11 Sweet peppers 1 0.10 Finland also supplied information on levels of dichlofluanid found in Finnish strawberries over the period 1975-1978. Table 7. Occurrence of residues in strawberries grown in Finland Number of samples containing Year Number of samples dichlofluanid levels within analysed given range, mg/kg <0.1 0.11-1.0 1.1-2.0 1975 98 34 7 - 1976 138 50 14 - 1977 139 48 20 - 1978 119 34 13 2 There was no explanation for the discrepancies in samples numbers. METHODS OF RESIDUE ANALYSIS The method of analysis in Sweden (1979) was reported to be that of Johansson (1978). Finland reported using a method of Johansson (1974) and Becker (1971). NATIONAL MRLs REPORTED TO THE MEETING The Swedish maximum acceptable level for dichlofluanid is 5 mg/kg for fruits and vegetables except potatoes. Sweden (1979). APPRAISAL Data supplied in 1977 from residue trials in Germany (F.R.) were based on legislation requiring analysis for total residues of dichlofluanid and metabolite which has since been changed, invalidating that data source. However, new data were received in 1979 from Japan and Finland which support the 1974 and 1977 recommendations for MRLs for apples, cucumbers, gooseberries, hops, strawberries and tomatoes. Sufficient information on national limits for blackberries, eggplants, peppers cereal grains and wheat straw was available to make it possible to retain the 1977 MRLs on a temporary basis until such time as valid data from supervised trials becomes available. Extensive information was received on the pathways of degradation and metabolism of dichlofluanid, including the fate of the fluorine-containing moiety of the molecule in plants (especially strawberries) and soil, satisfying the requirements of the 1977 Joint Meeting. Dichlofluanid is degraded fairly rapidly as the dichlofluoromethylmercapto group is easily cleaved off, leading to unstable intermediates and ultimately to thiazolidine-2-thione-4-carboxylic acid (TTCA), a reaction product of thiophosgene and cysteine. Soil residues degraded to CO2 and extractable products rapidly and extensively. After 63 days, 98.5% of applied radioactivity had evolved as 14C-CO2, while only 0.80% remained as extractable products. Data were received on the effects of processing on residues in strawberries. Washing reduced dichlofluanid residue from 5.9 mg/kg to 0.35 mg/kg. Further processing into pasteurized juice, canned fruits and jam reduced the residue to not detectable, 0.02 mg/kg, and not detectable respectively. The manufacturer of dichlofluanid has indicated that it is not recommending uses on leafy brassicas, negating the need for further residue data on this crop. RECOMMENDATIONS The temporary maximum residue limits recommended in 1977 for blackberries, eggplants, sweet peppers, cereal grain and wheat straw are retained on a temporary basis until data indicating the level of residues of the parent compound become available. The limits for all present and past recommendations refer to dichlofluanid only. Temporary maximum residue Commodity Limit, mg/kg Blackberries 15 Sweet peppers 2 Eggplants 1 Cereal grains 0.1 Wheat straw 0.5 FURTHER WORK OR INFORMATION Required by 1982 1. Residue data for dichlofluanid only, from supervised trials on blackberries, eggplants, peppers, cereal grains and wheat straw. 2. Studies to elucidate the accumulation seen in the thyroid. REFERENCES Becker, G. Gaschromatographische Simultan-Bestimmung von chlorierten Kohlenwasserstoffen und säureestern in pflanglichem Material. Dtsch. Lebensmittel.Resch. 67, 125 (1971). Belonozhko, G.A., et al. Hygienic Evaluation of Euparen Residues in Food Products (in Russian) Vop. Pitan. (2): 72-75. (Abstracted in Pesticide Abstracts 1979). Clark, T. and Watkins, D.A.M. - Photolysis of dichlofluanid. Pestic. Sci. 9, 225-228 (1978). Ecker, W. Biotransformation von (14c) Dichlofluanid in der Ratte. (1978) Unpublished report from Institut für Pharmakokinetik, submitted by Bayer AG. Finland. Submission from national government of reports of State Institute of Agricultural Chemistry, Helsinki. (1979). Flucke, W. Untersuchungen zur Acuten Toxizität bei Ratten, Mässen, Meerschweinchen Kanichen und Katzen. (1978) Unpublished report from the Institut für Toxikologie, submitted by Bayer AG. Haque, A., Westphal, D., Schuphan, I. and Ebing, W. Zusammengefabte Endergebnisse über das Abbau - und Metabolismus-verhalten von Tolylfuanid (Euparen M) in Erdbeeren. BBA-Berlin, Unveröffenlichter Bericht. (1979). Hartman, V.B., Wrieden, J.and Kirchhoffy J. and Gierschner, K. Daten und Dokumente zum Umweltschutz Sonderreihe Umweltagung, No. 23, Tagung Uber Umweltforachung der Universität Hohenheim, Schadstoffe in der Nahrungskette, Dokumentationestelle der Universität Hohenheim, January, 1979. Herbold, B. Mikronucleus-Test an der Maus zur Prüfung auf Mutagene Wirkung. (1978) Unpublished report from the Institut für Toxikologie, submitted by Bayer AG. Salmonella/Mikrosomen-Test zur Untersuchung auf Punktmutagene Wirkung. (1979a) Unpublished report from the Institut für Toxikologie, submitted by Bayer AG. Zytogenctische Untersuchungen der Spermatogonien beim Chinesisechen hamster zur Prüfung auf mugatene Wirkung. (1979b) Unpublished report from the Institut für Toxikologie, submitted by Bayer AG. Johansson, C.E. Var Zöda 26, 171 (1974) A multiresidue Analytical Method for Determining Organochlorine, Organophosphorus Dinitrphenyl and Carbamate Pesticide in Apples (modified) Pestic. Sci. 9, 313-322 (1978). Machemer, L. Dominant Lethal Study to Investigate Mutagenic Potential. (1974a) Unpublished Report from the Institut für Toxikologie, submitted by Bayer AG. Studies for Embryotoxic and Teratogenic Effects on Rats following oral administration. (1974b) Unpublished report from the Institute für Toxikologie, submitted by Bayer AG. Nitokuno Institute. (1972/76) Unpublished Analytical test results on residues ubmitted by Bayer AG. Reports Nos. 56/72, 39/73, 14/76, 15/76 on cucumbers. Report No. 86/78 on Hops. Reports Nos. 60/72, 61/72, 15/75, 16/75 on strawberries. Reports Nos. 55/72 and 13/76 on tomatoes. Reports No. 11/76 and 12/76 on watermelons. Schuphan, I., Ebing, W. - Gesamtergebnis der Untersuchungen zum Verhalten von Euparen WP (Dichlofluanid) im Boden (Abbau-Laborversuche). BBA-Berlin, unveröffentlichter Bericht. 1979a. Gesamtergebnis der Untersuchungen zum Verhalten von Eurpanen M WP (Tolylfluanid) im Boden (Abbau-Laborversuche). BBA-Berlin, unveröffentlichter Bericht. 1979b. Thyssen, J. Mitteilung vom 30.1.1978 in Ecker, W. 1978 opus cit. Vogeler, K., Steffan, H. Ullemeyer, H., Rapp, A. Zum Abbau von Dichlofluanid in und auf Weintrauben und bei der Weinbercitung. Bayer AG, Pflanzenschutz Anwendungstechnik, unveröffentlichter Bericht RA-97, 19.2.1979. Vonk, J.W., den Daas, H. Metabolism of (dichlofluoromethyl-14C) Tolylfluanid on apples. TNO Report, October 10, 1977. Westphal, D., Haque, A., Schuphan, I., and Ebing, W. Zusammengefabte Endergebnisse über das Abbau - und Metabolismus-verhalten von Dichlofluanid (Euparen) in Erdbeeren. BBA-Berlin, unveroffentlichter Bericht (1979).
See Also: Toxicological Abbreviations Dichlofluanid (FAO/PL:1969/M/17/1) Dichlofluanid (WHO Pesticide Residues Series 4) Dichlofluanid (Pesticide residues in food: 1977 evaluations) Dichlofluanid (Pesticide residues in food: 1981 evaluations) Dichlofluanid (Pesticide residues in food: 1982 evaluations) Dichlofluanid (Pesticide residues in food: 1983 evaluations)