FAO/PL:1968/M/9/1 WHO/FOOD ADD./69.35 1968 EVALUATIONS OF SOME PESTICIDE RESIDUES IN FOOD THE MONOGRAPHS Issued jointly by FAO and WHO The content of this document is the result of the deliberations of the Joint Meeting of the FAO Working Party of Experts and the WHO Expert Committee on Pesticide Residues, which met in Geneva, 9-16 December, 1968. FOOD AND AGRICULTURE ORGANIZATION OF THE UNITED NATIONS WORLD HEALTH ORGANIZATION Geneva, 1969 CHLOROBENZILATE This pesticide was evaluated for acceptable daily intake by the 1965 Joint Meeting of the FAO Committee on Pesticides in Agriculture and the WHO Expert Committee on Pesticide Residues (FAO/WHO, 1965). Since the previous evaluation, additional data has become available and the monograph has been greatly expanded and is reproduced in its entirety. IDENTITY Biological activity acaricide Chemical names ethyl 4,4'-dichlorobenzilate ethyl 2-hydroxy-2,2-di(p-chlorophenyl)-acetate. (IUPAC) Synonyms Acaraben(R), Akar(R), Gesaspint(R) Structural formulaOther information on identity and properties The technical material consists of a yellow-brown oily liquid with a purity of at least 90 per cent. No data have been submitted on the composition of the technical product. EVALUATION FOR ACCEPTABLE DAILY INTAKE Biochemical aspects Three groups, each containing one male and one female dog, were given 0, 12.8, or 64.1 mg/kg/day for five consecutive days. At autopsy, five days after the termination of treatment, no residues could be detected in whole blood, liver, kidney, muscle, fat, or brain tissues. At 12.8 mg/kg/day, the male excreted 31 per cent of the total dose in the urine within 10 days. Urinary excretion in the female accounted for 41 per cent. Faecal levels contained 5.6 per cent and 6.6 per cent for the male and female respectively. At 64.1 mg/kg/day urinary and faecal elimination was 31 per cent and 1.7 per cent respectively for the male, and 23 per cent and 26 per cent for the female. The method of analysis would not detect conjugates of 4,4'-dichlorobenzilic acid which is suggested to be the major metabolite (Hazleton Laboratories Inc., 1964). Dichlorobenzilic acid has been qualitatively identified in dog urine by thin-layer chromatographic techniques (Mattson et al., 1965). Acute toxicity (oral) Animal Route Compound or LD50 (mg/kg Reference solvent body-weight) Mouse Oral Suspension in 4 850 Gasser, 1952 gum arabic Mouse Oral Technical 729 Horn et al., 1955 material Rat Oral Suspension in 3 100 Gasser, 1952 gum arabic Rat Oral Technical 702 Horn et al., 1955 material Rat Oral 25 per cent. 735 Horn et al., 1955 xylene emulsion Short-term studies Avian wildlife Groups of 10 Mallard ducks (Aras platyrhynchus) were fed 0, 0.25, 0.45 and 0.8 per cent of chlorobenzilate for five consecutive days. The LD50 was greater than 0.8 per cent. Body-weight gain and food intake was slightly reduced in all test groups (Woodard, 1965a). Groups of 10 quail (Colinus virginianus) were fed 0, 0.14, 0.25 and 0.5 per cent of chlorobenzilate in their diet for seven days. The LD50 was 0.34 per cent. Bodyweight, food intake and gross pathology of the survivors appeared unaffected (Woodard, 1965a). Rat Groups, each of 20 male rats, were fed 0, 40 and 800 ppm technical chlorobenzilate in their diet for 48, 48 and 44 weeks, respectively. Mortality was slightly higher in the 800 ppm group than in the control group. The growth of the animals fed 800 ppm was retarded, and several animals exhibited red or swollen eyelids and soft faeces. Organ to body-weight ratios for the 40 ppm group were significantly greater than for the controls, in the case of liver, kidney and testes. Similar data for the 800 ppm group were not evaluated statistically, but organ to body-weight ratios in the case of the liver and kidney appear to be greater than for the controls. Gross pathological examination revealed no changes attributable to compound administration, but upon histological examination non-specific changes were observed in the pancreas and adrenals of animals in both test groups, and increased hemopoietic activity in the spleens of the 800 ppm groups. Tissue analysis indicated that chlorobenzilate was not stored in the animal to any appreciable extent (Hazleton Laboratories, 1953a). Groups of five male rats received 0, 1, 3 or 5 per cent technical chlorobenzilate in the diet, and groups of five female rats received 0, or 3 per cent, in the diet. All animals receiving chlorobenzilate at these levels died, those receiving one per cent within 59 days, three per cent within eight days, and five per cent within six days. Reduced food consumption, and marked loss of body-weight preceded death.(Hazleton Laboratories, 1953b). A 15 week feeding study, utilizing groups of five male rats at dose levels of 0, 500, 1000, or 5000 ppm technical chlorobenzilate resulted in reduced food consumption, and growth retardation in all test groups. Mortality was 40 per cent at 1000 ppm, and 100 per cent at 5000 ppm (Hazleton Laboratories, 1953b). In a 17 week feeding study using groups of 20 male rats fed 0, 50, and 500 ppm, and 20 female rats at 0, and 500 ppm, body weight gain was depressed in the male only, at 500 ppm. Food intake was not significantly depressed (Hazleton Laboratories, 1953b). Groups of 20 male and 20 female rats treated for 99 days, with a 20 per cent chlorobenzilate powder mixed in their diet at dose levels of 0, 20, 100, 500, and 2500 ppm active ingredient did not show any toxic effects as judged by food consumption, body-weight, mortality, organ weights, gross, or histopathology except at the top dose level. At 2500 ppm active ingredient, food intake was reduced initially, body-weight gain was reduced, absolute testes and spleen weights were below control levels (insufficient data available to calculate organ to body-weight ratios), and histopathological examination revealed three rats with increased fatty deposits in the liver lobules, as well as five rats with spermatogenentic injury, and testicular atrophy (Domenjoz, 1965a). Dog Pairs of dogs (one male and one female) were fed 12.8, or 64.1 mg/kg five times weekly for 35 weeks, except for two periods of five days when excretion studies were performed. No toxic effects were apparent, judging by growth, general appearance, hematology, urinalysis, liver function test, and gross and microscopic pathology. The excretion studies showed that the majority of administered material was excreted in the urine, the metabolite having a 4,4'-dichlorodiphenyl methyl structure. No chlorobenzilate was present in the urine three days after withdrawal (Horn et al., 1955). In a two year feeding study utilizing the 25 per cent powder formulation, groups of three male and three female dogs were fed 0, 100, or 500 ppm active ingredient in the diet. A further group of three male and three female dogs were fed 5000 ppm active ingredient for 14 weeks. One male and one female were maintained at this dose level for 20 weeks when they were sacrificed. The remainder, after a five week withdrawal period, were replaced in the study by a 3000 ppm dose level, until the completion of the test. At 100, and 500 ppm, the parameters considered were comparable to the control group. At 3000 ppm, body-weight depression, mild anaemia and increased liver and spleen to body-weight ratios were observed in both sexes. At 5000 ppm, in addition to these effects, food intake was depressed, anaemia was moderately severe, serum alkaline phosphatase values were elevated, and the albumen to globulin ratio was reversed. The histopathology, presumably performed at 104 weeks, indicates no compound related effects at 100 and 500 ppm. At the top level, extramedullary haematopoiesis was evident in liver and spleen as well as erythroid hyperplasia of the bone marrow (Hazleton Laboratories Inc., 1965). Sheep and beef-cattle Sheep were exposed to chlorobenzilate 25 per cent wettable powder in the diet for four weeks at dose levels of 0 (two females), 3.6 (two females), 8.7 (two females) or 29 (one male and four females) ppm active ingredient, and beef-cattle at dose levels of 0 (one male and one female), 3.2 (one male and one female), 8.8 (one male and one female), or 27 (one male and one female) ppm active ingredient. The sheep and cattle failed to show compound related toxic symptoms as judged by food consumption, bowel evacuations, physical condition and behaviour, haematology, or gross necropsy observation. One cow dosed at 3.2 ppm aborted a six-month foetus on day four. However, a second cow dosed at 8.8 ppm carried a fully-developed foetus until sacrificed (Woodard, 1965c). Long-term studies Rat A two year study, using technical chlorobenzilate at 0 (20 male and 20 female), 50 (20 male) and 500 ppm (20 male and 20 female) showed decreased body-weight gain, as well as unthriftiness, and blood tinged crusts about the nose and eyes at 500 ppm. An increased incidence of testicular atrophy was noted at both 50 and 500 ppm without histological change (Horn et al., 1955). A second two year study utilizing groups of 30 male and 30 female rats at dose levels of 0, 40, 125 and 400 ppm active ingredient as the 25 per cent wettable formulation showed no significant changes in body-weight gain, or food intake. Haematologic values did not show any consistent changes related to dose level, or length of exposure to the test material. Incidence of neoplasms was unrelated to the administration of the test substances. Adverse effects on organ to body-weight ratios were noted in the case of liver at 400 ppm. In the histopathological examination of tissues, changes were observed in liver, kidney and testes at 400 ppm, and in kidney and testes at 125 ppm. Gross autopsy observations indicated testicular changes at 125 and 400 ppm (Woodard, 1966). Special studies (a) Reproduction A three generation study, utilizing 20 male and 20 female rats at 0, and 50 ppm active ingredients as the 25 per cent wettable formulation in the first generation, and, 10 male and 20 female rats at 0, 25 and 50 ppm active ingredient in the second and third generations failed to reveal any toxic effects on adult body-weight, resorption rates, or histology (performed on F1b adults). Absolute testes weights for the F1b adults (the only group reported) showed a significant decrease at 50 ppm active ingredient. The litters all appeared normal as judged by litter size, birth weight, stillbirths, survival to weaning, weanling weights, and F3b weanling histopathology. Adult fertility, as judged by number of litters per group appeared normal, but chlorobenzilate withdrawal at weaning for 15 days, and at weaning for 28 days in F1b and F2b weanlings, respectively, leaves this parameter open to question. No teratogenic changes were observed at any stage in the study (Woodard, 1965b). (b) Studies on the metabolite The metabolite, dichlorbenzilic acid was fed to groups of 20 male and 20 female rats for 99 days at dose levels of 0, 20, 100, 500 and 2500 ppm active ingredient in a 20 per cent powder. Food consumption body-weight gain, mortality, organ weights, and gross and histopathology showed no significant changes from the controls, except possibly for a slight depression of kidney and testes weight at 2500 ppm (Domenjoz, 1965b). Comments Adequate data have been presented on short-term and long-term studies in rats and dogs. Biochemical data on excretion, and a tentative identification of the major metabolite are also available. All the studies appear to be reliable and sufficiently adequate to permit evaluation. The slight doubts regarding the incidence of neoplasms observed in the long-term study on the rat makes it desirable to obtain information from a second species. TOXOCOLOGICAL EVALUATION Level causing no significant toxicological effect Rat: 40 ppm in the diet, equivalent to 2 mg/kg body-weight Dog: 500 ppm in the dry diet, equivalent to 12.5 mg/kg body-weight Estimate of acceptable daily intake for man 0-0.02 mg/kg body-weight RESIDUES IN FOOD AND THEIR EVALUATION Use pattern Pre-harvest treatments Chlorobenzilate is used as a contact acaricide for the control of adult spider mites; it is also effective against summer eggs and all post-embryonic stages. The compound is used in many countries throughout the world for the control of several mite species on apples, pears, stone fruits, citrus fruits, soft fruit, grapes, olives, vegetables, coffee, tea, cotton and ornamentals. Chlorobenzilate is less effective at lower temperatures, and in countries with a temperate climate, it is primarily used on glass-house crops and only to a small extent outdoors. In view of its specific acaricidal activity and its non-toxicity to bees, it may be usefully applied in integrated control schemes. In certain instances it is being recommended when resistance to other acaricides has developed. The recommended rates of application range from 25-50 g/100 l, and the mount of spray liquid applied is generally 500-1000 l/ha for low-grown crops (vegetables, etc) and 2000-2500 l/ha for high-grown crops (e.g. fruit orchards). (U.S. Dept. of Agric., 1967) Post-harvest treatments No post-harvest treatment is recommended. Other uses Chlorobenzilate is being used for the control of mites on ornamental plants. The compound is also used as a smoke for the treatment of bee-hives against tracheal mites (Gubler, 1953). Residues resulting from supervised trials Residue data are available from supervised trials on several food crops, grown under various conditions, using various rates of application and pre-harvest intervals (Geigy, 1968). These data refer to apples, citrus, nuts and vegetables (melons, cantaloupes). In most cases normal dosage rates were applied in accordance with label recommendations; in a few experiments higher dosages were included. Results mainly refer to work in the United States of America. Only limited data are available from other countries. The following table summarizes typical residue data. Rate of Post treatment Residue, *** Crop application Number of interval whole fruit (g/100 1) treatments (days) basis (ppm) Apples 31 1 1 2.24 31 1 8 1.79 62 1 1 4.98 62 1 8 4.33 25 1 6 0.72 25 1 35 0.41 60 1 39 0.90 Grapefruit 30 1 1 1.10* 30 1 22 2.04* Oranges 30 1 1 1.22* 30 1 22 1.99* Grapes 60 1 17 0.62* 60 1 34 1.06* 120 1 17 1.20* 120 1 34 1.15* Almonds 45 1-2 0-63 < 0.1 Melons 0.56** 1 1 < 0.04-0.4 0.56** 1 14 < 0.04-0.13 2.24** 1 1 0.08-1.1 2.24** 1 14 0.09-0.39 * Based on peel; analysis of pulp showed residues of less than 0.1 ppm in the case of apples - no data on residues in pulp of grapes. ** kg/ha *** UV method (Blinn and Gunther, 1963) except GLC (see below) for grapes, almonds and melons. Fate of residues General comments Chorobenzilate can be considered as a persistent compound. More information is needed on the nature of terminal residues in plants, animals and their products. In soils No information available. In plants Experiments have been carried out to examine if and to what extent breakdown products derived from chlorobenzilate could be found, with particular reference to the possible occurrence of 4,4'-dichlorobenzilic acid after apples were sprayed with 2 lbs/ 100 gal and samples were taken 3, 14 and 21 days. The sensitivity of the analytical method was 0.1 ppm. In recovery studies, 4,4'-dichlorobenzilic acid could be detected without interference of chlorobenzilate. It appears that chlorobenzilate is found mainly on the outer surface of the treated apples. No unchanged chlorobenzilate could be detected in the pulp of the apples. None of the treated apples contained detectable amounts of 4,4'-dichlorobenzilic acid (Murphy et al., 1966). In animals In experiments on sheep and cattle (Mattson and Schneller, 1966) 16 per cent protein mixed grain containing chlorobenzilate was given in addition to a daily ration of mixed timothy and clover hay to eight sheep and six cattle (both sexes) over a period of four weeks. The dosage levels were 10, 24 and 80 mg chlorobenzilate per animal per day for sheep and 40, 110 and 340 mg chlorobenzilate per animal for cattle. Residues of unchanged chlorobenzilate were only found in cattle at the highest feeding level (340 mg/animal/day). Residues in cattle (ppm in fat) Males Females subcutaneous fat 0.54 0.32 omental fat 0.98 0.69 perirenal fat 0.54 0.69 In another experiment (Woodard, 1960) chlorobenzilate was administered to six dairy cows at dietary levels of 20, 48 and 160 ppm in the feed (intake 4 lbs of treated feed per day) for a period of 15 days. After 16 days, treatment with chlorobenzilate was terminated and the animals were given the same type of feed, without chlorobenzilate, to permit post-treatment analysis of milk samples. Milk samples were taken on the second, fourth, sixth, ninth and fifteenth days of the experiment, and again on the twentieth, twenty-first and twenty-second day. Chlorobenzilate in the milk was found in one "high-level" cow (160 ppm) on the second day (0.15 ppm) and in one "medium-level" cow (48 ppm) on the fourth day (0.15 ppm). On the fifteenth day, residues did not exceed 0.06 ppm. Since these levels are approaching the limit of sensitivity of the analytical method used, there is no distinct correlation between residue and feeding levels, and a number of negative values were obtained, the few positive values may be fortuitous. No 4,4'-dichlorobenzilic acid was found in the milk. Limited recovery studies show that this compound, if present, would be detected with the methods used. In the above short-term feeding experiments rather high dosages have been used, and more information is required on the possible occurrence of residues in milk after feeding normal dosage levels for a prolonged period. In storage and processing No data are available on the fate of residues during storage and processing. Since the residue remains mainly on the outer side of fruit and migrates only to a very small extent or not at all into the pulp, it may be expected that washing and peeling of treated fruit will remove most of the residue. No data are available on the effect of cooking. Evidence of residues in food in commerce or at consumption Food moving in commerce No information available. Food at the time of consumption In "market basket" or "total diet" studies (Cummings, 1966), carried out by the United States Food and Drug Administration, multidetection methods were used for residue analysis. The analytical procedure used for all samples in this study enabled the detection of about 54 pesticide chemicals, including chlorobenzilate. So far no residues of chlorobenzilate have been found. Methods of residue analysis Several methods are available for residue analysis of chlorobenzilate, e.g. ultra-violet or infra-red spectrophotometry and gas-liquid chromotography. In former years the ultra-violet method, as described by Blinn and Gunther (1963) was used for determination of chlorobenzilate residues on apples, pears and citrus fruit. In addition Harris (1955) developed a modified Schechter-Haller infra-red spectrophotometric method for residue analysis of chlorobenzilate. This method was suitable for residue analysis on apples, pears and strawberries. A modification of this method is described by Margot and Stammbach (1964). At present a gas chromatographic method appears to be most suitable for use as a referee method, and should be developed for this purpose through collaborative studies, in particular, the comparative evaluation of the different detectors. The following is a brief description of the gas chromatographic determination of chlorobenzilate and chloropropylate in fruits, vegetables and nuts. The method is sensitive to 0.05 ppm: Chlorobenzilate and chloropropylate are extracted from the chopped material with petroleum ether (boiling range 30-60°C). Part of the extract is evaporated to dryness, taken up in benzene and transferred to an alumina column (basic, activity grade V). Interfering materials are removed by eluting with hexane or with 10 per cent benzene in hexane. Chlorobenzilate and chloropropylate are eluted with hexane/benzene (1:1) and the content is determined by gas chromotography using a glass column (4 ft × 0.25 in) packed with five per cent silicone gum GE XE - 60 (nitrile) supported on Anakrom ABS (50-60 mesh) with nitrogen as the carrier gas and a microcoulometric detector. Conditions: oven temperature, 215-220°C; block temperature, 220-225°C; furnace temperature, 810-820°C; nitrogen flow, 80 ml/min; oxygen flow, 100 ml/min; pure nitrogen flow, 110 ml/min. Conditioning of the column is important and can be achieved by three to four injections of 30 micrograms of the acaricide. Retention times are approximately 4 min. Separation of chlorobenzilate and chloropropylate can be obtained by using a column loading of 10 per cent XE-60 and a column length of 6 ft (retention times approximately 18 min for chlorobenzilate and 20 min for chloropropylate). Apples, pears, stone fruits, citrus fruits, berries, nuts, vegetables and cotton have been analysed for chlorobenzilate. Apples, pears, stone fruits, citrus fruits, almonds, cucumbers and beans have been analysed for chloropropylate. Typical recovery data with fortified samples (sample weight 1-5 g) are: Per cent recovery Crop Chlorobenzilate Chloropropylate Green beans 73-100 (continued) Per cent recovery Crop Chlorobenzilate Chloropropylate Maize (ears) 80-120 Maize (foliage) 80-95 Ground nuts 78-80 Citrus (peel) 89-110 Citrus (pulp) 70-80 Pears (peel) 90-100 Pears (pulp) 100-110 For oleagenous samples such as nuts, seeds and citrus peel, an additional petroleum ether-acetonitrile partitioning step is necessary. Using the described clean-up procedure no interference from DDT and DDD is encountered. National tolerances Country Crop Tolerance (ppm) Canada apples, pears, citrus fruit, cantaloupes 8 Netherlands fruit and vegetables 2 New Zealand fruit and vegetables 5 United States of America apples, pears, citrus fruit, melons 5 almonds, walnuts 0.2 almond hulls 15 cotton-seed 0.5 meat, fat and meat by-products 0.5 of cattle and sheep (United States of America Federal Register) RECOMMENDATIONS FOR TOLERANCES AND PRACTICAL RESIDUE LIMITS Appraisal Chlorobenzilate is a persistent and specific acaricide used on a fairly wide range of crops. In many instances it is active against mites which have developed resistance to other acaricides. The compound is non-toxic to bees, and may be usefully applied in integrated control schemes. Although the compound is registered in many countries, little information was available on the extent of the use in these countries. Many of the data furnished are based upon experiments which have been conducted in the United States of America. Furthermore, no information was available on the total composition of the technical product. The compound has not been detected in total diet studies in the United States of America. There was a lack of data on the disappearance of the compound and the disappearance of residues during storage and processing. Information is required on the possible carry-over of the residue into wine before tolerances for grapes can be recommended. Although data were provided on residues in milk following feeding at excessively high dosages to dairy cattle for a short period of time (16 days), there were no data furnished on possible residues in milk following the feeding of treated feed at normal residue levels for longer periods. However, the residue occurring as the result of these high-level feeding trials was at the limit of detection of the analytical method (0.05 ppm) and it would not be expected that a higher residue level would result from feeding lower levels for longer periods in view of the fact that the compound is not cumulative. In animals the compound is metabolized to form 4,4'-dichlorobenzilic acid. No information is available on the nature of the terminal residues in plants and in animal products. A referee method of analysis has not been established, although gas-liquid chromatography would seem to be most suitable for this purpose, but must be further developed by collaborative studies. Comparative evaluation of the different detectors used in gas chromatographic methods, and evaluation of different methods of extraction are needed. Recommendations The following temporary tolerances (to be in effect until 1972) are to apply to raw agricultural products moving in commerce unless otherwise indicated. In the case of fruits and vegetables, the tolerances should be applied as soon as practicable after harvest and in any event prior to actual retail to the public. In the case of commodities entering international trade, the tolerances should be applied by the importing country at the point of entry or as soon as practicable thereafter. The tolerances are for the parent compound only. apples, pears (whole fruit basis) 5.0 ppm citrus (whole fruit basis) 1.0 ppm melons, cantaloupes 1.0 ppm almonds, walnuts 0.2 ppm Further work or information Required before 30 June 1972 1. Information on the composition of the technical product. 2. Information on the nature of terminal residues in plants, animals, and their products. 3. Data from countries other than the United States of America on the required rates and frequencies of application, pre-harvest intervals, and the resultant residues. 4. Further data on the disappearance of residues in soils, in plants, and in plant products during storage and processing. 5. Data on the possible carry-over of residues into wine as a result of the treatment of grapes. 6. Further data on the occurrence of residues in milk after feeding dairy cows at normal residue levels of the compound in the feed. 7. Comparative evaluation of the different detectors used in gas liquid chromatographic methods and of different methods of extraction for regulatory purposes. Desirable 1. Collaborative studies to establish a referee method. 2. Metabolic studies in animals. 3. Investigation of possible testicular effects and long-term studies in species other than the rat on the incidence of neoplasms. REFERENCES Blinn, R. C. and Gunther, F. A. (1963) The utilization of infrared and ultraviolet spectrophotometric procedures for assay of pesticide residues. Residue Reviews 2: 99-152 Cummings, J. G. (1966) Pesticides in the total diet. Residue Reviews 16: 30-45 Domenjoz, R. (1965a) Chlorbenzilat Toxizität bei chronischer Verabreichung. Institute of Pharmacology, Rheinische Friedrich-Wilhelm's University, Bonn. Unpublished report. Domenjoz, R. (1965b) Dichlorbenzilsäure Toxizität bei chronischer Verabreichung. Institute of Pharmacology, Rheinische Friedrich-Wilhelm's University, Boon. Unpublished report. FAO/WHO. (1965) Evaluation of the toxicity of pesticide residues in food. FAO Mtg Rept No. PL:1965/10/1; WHO/Food Add./27.65 Gasser, R. (1952) Über zwei neue Akarizide aus der Gruppe der Di-(p- chlorphenyl)-karbinole. Experientia, 8: 65-67 Geigy S.A., J.R. (1968) Chlorobenzilate working paper. Unpublished report. Gubler, W. et al. (1953) Schweizerische Bienenzeitung, 7: 268 Harris, H. J. (1955) Colorimetric determination of ethyl 4,4'-dichlorbenzilate (chlorobenzilate) as a spray residue. J. Agr. Food Chem., 3: 939-941 Hazleton Laboratories Inc. (1953a) Geigy 338, technical. Chronic feeding - rats. Unpublished report Hazleton Laboratories Inc. (1953b) Geigy 338, technical feeding studies - rats. Unpublished report Hazleton Laboratories Inc. (1964) Method and development for the analysis of chloropropylate and chlorobenzilate in biological fluids and tissue specimens. Metabolic distribution and excretion of chloropropylate and chlorobenzilate in dogs. Unpublished report Hazleton Laboratories Inc. (1965) Chlorobenzilate. Two year dietary feeding study - purebred beagles. Unpublished report Horn, H. J., Bruce, R. B, and Paynter, O.E. (1955) Toxicology of chlorobenzilate. J. Agr. Food Chem., 3: 752-756 Industrial Bio-Test Laboratories. (1965) Report to Geigy Chemical Corp. Acute toxicity studies on chlorobenzilate 25W. Unpublished report Margot, A. and Stammbach, K. (1964) Chlorobenzilate; in: Zweig, G., 1964. Analytical methods for pesticides, plant regulators and food additives. Academic Press, London and New York, Vol. 2, 65-73 Mattson, A. M., Beaudoin, R. L. and Schneller, J. (1965) Comparison of urinary metabolites in dogs after administration of chlorobenzilate or chloropropylate. Analytical Dept. of Geigy Research Laboratories. Unpublished report Mattson, A. M. and Schneller, J. (1966) Chlorobenzilate residues in sheep and cattle tissues. Unpublished report of the Analytical Department of Geigy Research Laboratories, Division of Geigy Chem. Corp., Ardsley, New York. Murphy, R., Kahrs, R. and Mattson, A. M. (1966) Dissipation of residues of chlorobenzilate and chloropropylate on apples. Unpublished report of the Analytical Department of Geigy Research Laboratories, Division of Geigy Chem. Corp., Ardsley, New York United States of America Federal Register, 27, F.R. 12092, pav. 120-129 United States of America Department of Agriculture. (1966) Summary of registered pesticide chemical cases. 1st October Woodard. (1960) Examination of milk for residues following feeding of chlorobenzilate to dairy cows. Unpublished report, Woodard Research Corp. Woodard. (1965a) Chlorobenzilate. Safety evaluation on fish and wild life. (Bobwhite quail, mallard ducks, rainbow trout, sunfish, goldfish, oysters). Unpublished report, Woodard Research Corp. Woodard. (1965b) Chlorobenzilate. Three generation reproduction study in the rat. Unpublished report, Woodard Research Corp. Woodard. (1965c) Safety evaluation and determination of the amount of chlorobenzilate that might appear in the tissues of sheep and beef-cattle fed this material in the diet for four weeks. Unpublished report, Woodard Research Corp. Woodard. (1966) Chlorobenzilate. Safety evaluation by dietary feeding to rats for 104 weeks. Unpublished report, Woodard Research Corp.
See Also: Toxicological Abbreviations Chlorobenzilate (ICSC) Chlorobenzilate (FAO Meeting Report PL/1965/10/1) Chlorobenzilate (WHO Pesticide Residues Series 2) Chlorobenzilate (WHO Pesticide Residues Series 5) Chlorobenzilate (Pesticide residues in food: 1977 evaluations) Chlorobenzilate (Pesticide residues in food: 1980 evaluations) Chlorobenzilate (IARC Summary & Evaluation, Volume 5, 1974) Chlorobenzilate (IARC Summary & Evaluation, Volume 30, 1983)