FAO, PL:CP/15 WHO/Food Add./67.32 EVALUATION OF SOME PESTICIDE RESIDUES IN FOOD The content of this document is the result of the deliberations of the Joint Meeting of the FAO Working Party and the WHO Expert Committee on Pesticide Residues, which met in Geneva, 14-21 November 1966.1 1 Report of a Joint Meeting of the FAO Working Party and the WHO Expert Committee on Pesticide Residues, FAO Agricultural Studies, in press; Wld Hlth Org. techn. Rep. Ser., 1967, in press CARBARYL IDENTITY Synonym Sevin(R) Chemical names 1-naphththyl-N-methylcarbamate; N-methyl-1-naphthyl carbamate; N-methyl-a-naphthyl urethane. FormulaBIOLOGICAL DATA AND TOXICOLOGICAL EVALUATION Biochemical aspects Some knowledge has been obtained of the changes which the compound undergoes in plants. Following injection of 14C-carbaryl into the stems of snapbeans and cotton seedlings, 55 per cent of the activity injected was present in the beans, and 86 per cent in the cotton, at 28 days. Of the original compound, 5.7 per cent was found in the beans and 1.7 per cent in the cotton. It is suggested that conversion to water-soluble metabolite(s), which may have been carbamates, took place and these were quite stable within the plants (Dorough & Casida, 1964). A slight rise in free 1-naphthol and a definite rise in conjugated 1-naphthol in the urine were observed during the 48 hours following oral dosing of carbaryl in rats (Carpenter et al., 1961). Among workers engaged in the production, handling and shipping of carbaryl, those most heavily exposed (air concentrations of 0.23 to 31 mg/M3) excreted large amounts of total 1-naphthol (Best & Murray, 1962). 14C-carbaryl, labelled at the N-methyl, carbonyl and naphthyl-1 positions, and metabolized by rat liver microsomes and insects, yielded at least 5 metabolites (Dorough et al., 1963). Further work has shown the existence of 6 metabolites, 5 of which were carbamates. Three of these were tentatively identified as 1-naphthyl N-hydroxymethylcarbamate, 4-hydroxy-1-naphthyl-N-methylcarbamate and 5-hydroxy-1-naphthyl-N-methylcarbamate (Dorough & Casida, 1964). When 14C-carbonyl carbaryl was given orally to a goat in a dose of 1.34 mg/kg, several of these metabolites were found in the milk and urine. The level of total 14C equivalents of carbaryl reached a peak of 0.93 ppm in the milk at 8 hours and decreased to below 0.003 ppm at 60 hours. During the 96 hours after dosing, 47 per cent of the radioactivity was excreted in the urine (Dorough et al., 1963; Dorough & Casida, 1964). In rats and guinea-pigs, 7 days after ingestion of labelled carbaryl, the overall recovery of 14C-methyl, 14C-carbonyl and 14C-naphthyl labels was, respectively, 95, 99 and 91 per cent of the dose of carbaryl. The only detectable 14C residues in the rat were from 14C-methyl, representing 2-3 per cent of the dose. Several metabolites were identified, and two of these, 1-naphthyl glucuronide and sulfate, were also detected in urine from men exposed to carbaryl dust (Knaak et al., 1965). When carbaryl, labelled with 14C at the carbonyl, methylcarbamate or naphthyl groups, was given to male rats by intraperitoneal injection, recovery of 14C the expired CO2 after 48 hours was 24.5, 12.3 and 0.2 per cent respectively. At 24 hours, respective urine recoveries were 62.1, 54.6 and 74.2 per cent and at 48 hours, 2.4, 3.4 and 2.3 per cent. Recoveries from faeces at 48 hours were 2.1., 3.9 and 8.9 per cent, and from carcass, 9.5, 12.7 and 6.7 per cent. After giving 14C-carbonyl carbaryl to male and female rats, no marked sex differences were noted (Krishna & Casida, 1966). Technical carbaryl was fed to dairy cows at levels up to 450 ppm for 2 weeks. Samples of milk taken at various times failed to disclose any measurable residues. Carbaryl, if present, was below the sensitivity of the method (0.01 ppm) (Gyrisco et al., 1960). In steers fed 50 or 200 ppm daily of technical carbaryl for 27 days, no tissue residues could be detected (Claborn et al., 1963). Milk from cows 1 hour after being sprayed to runoff with 0.5 per cent carbaryl solution or after having received a tablespoon of 50 per cent dust spread down the back, contained carbaryl residue. Samples taken at 15, 25 and 37 hours contained no residue (Eheart et al., 1962). Milk taken as early as 5 hours after the last spray from 2 cows sprayed 4 times at 4 day intervals with 0.5 per cent carbaryl suspension did not contain carbaryl. Omental fat taken from 2 steers 5 days after the fourth spraying did not contain carbaryl or 1-naphthol (Roberts et al., 1960). Carbaryl residue, 1-naphthol and conjugate varied from 0-0.57 ppm in various tissues from steers, sheep, goats and hogs 1 day after being sprayed to runoff with 1 per cent water suspension of 50 per cent carbaryl powder. At 7 days no residue could be detected except in fat and brain of the goat (Claborn et al., 1963). In laying hens dusted 3 times at 4-day intervals with 4 g of 5 per cent carbaryl dust per bird and killed 24 hours after the last dusting, concentrations of less than 0.1 to 2.0 ppm carbaryl residue and less than 0.1 ppm of 1-naphthol were found in breast and leg muscle. Liver and gizzard concentrations of both residues were less than 0.2 ppm. Residue concentrations in eggs remained below 0.2 ppm throughout the study (Johnson et al., 1963). A depression of blood and brain cholinesterase activity has been reported following single large doses of carbaryl. Approximately the same concentrations are required to produce a 50 per cent inhibition in the blood of man, rabbit, rat and dog (Mellon Institute, 1958b). No significant effect was found on dog erythrocyte or plasma cholinesterase after single intravenous injections of 10 or 15 mg/kg. In a dog which had received a total of 88.3 mg/kg in 11 doses intravenously, typical symptoms of cholinesterase inhibition occurred after 10 and 15 mg/kg, but only a slight reaction was seen after 5 mg/kg (Carpenter at al., 1961). In men exposed to carbaryl air concentrations of 0.23 to 31 mg/M3 whole blood cholinesterase activity was occasionally slightly depressed but there were no clinical signs (Best & Murray, 1962). Carbaryl is a reversible cholinesterase inhibitor. In fact, the reversal is so rapid that unless special precautions are taken, measurements of blood cholinesterase of persons exposed to it are likely to be inaccurate and always tending to appear normal. Pyridine-2-aldoxime methiodide, which is a good antidote for some organophosphorus compounds, is not effective in reversing cholinesterase inhibition by carbaryl (Mellon Institute, 1958b; Carpenter at al., 1961). Atropine sulfate was effective in controlling symptoms in the dog (Carpenter at al., 1961). Special studies Some studies have been reported describing the effects of a single administration of carbaryl on discrete avoidance and food reward behavioural tests in rats. In one report (Goldberg at al., 1965a) the dose necessary to suppress avoidance response to 50 per cent efficiency was slightly lower than the dose required to reduce brain cholinesterase to 50 per cent of control value. The effects of carbaryl on behaviour are prevented by atropine pre-treatment, and the association with Chlorpromazine leads to more than additive effects. Beta-dimethylaminoethyl-diphenylpropyl-acetate (SKF 525) increases the behavioural effects of carbaryl without enhancement of cholinesterase inhibition (Goldberg & Johnson, 1964a; Goldberg & Johnson, 1964b; Goldberg et al., 1965a; Goldberg et al., 1965b). Acute toxicity Animal Route Solvent LD50 References mg/kg Mouse i.p. Corn oil 25 Barron et al., 1964 Rat, male oral 10% Tween 80 190 Mellon Institute, 1956a Rat, male oral 10% Tween 80 310 Mellon Institute, 1958a in 0.75% NaCl Rat, male and female oral 0.25% agar 480-610 Mellon Institute, 195ba Rat, male oral Peanut oil 850 Gaines, 1960 Rat, female oral Peanut oil 500 Gaines, 1960 Rat, male oral Corn oil 308 Mellon Institute, 1958a (continued) Animal Route Solvent LD50 References mg/kg Rat, female oral Corn oil 560 Mellon Institute, 1958a Rat i.v. Propylene glycol 18 Mellon Institute, 1958a Rat i.v. PEG 400 24 Mellon Institute, 1958a Rat i.v. Undiluted 93 Mellon Institute, 1958a Guinea-pig, male oral 0.25% agar 280 Mellon Institute, 1958a Rabbit, male oral 0.25% agar 707 Mellon Institute, 1958a Dog oral Powder none died Mellon Institute, 195ba (250-795 mg/kg) Chicken. Focal loss of striation and fatty infiltration of muscle was observed at 3 g/kg subcutaneously. Transient leg weakness for 1-2 days occurred after 2 g/kg and a nephrotoxic action was observed after 2 g/kg or more. No demyelination was seen (Carpenter et al., 1961). Man. A 19-month-old child swallowed an unknown amount of carbaryl. Typical early signs of cholinesterase inhibition, i.e. constricted pupils, excessive salivation, and muscle incoordination, occurred. A single dose of atropine of 0.3 mg controlled the symptom and the child recovered in 12 hours. Urine collected 18 hours after poisoning contained 3140 µg of 1-naphthol per 100 ml (Best & Murray, 1962). Short-term studies Mouse. In one experiment 30 A/Jax and 30 C3H mice at the age of 3 months were started on a treatment of weekly subcutaneous injections of 0.5 mg of carbaryl. Five months later, the survivors (26 A/Jax and 28 C3H) were sacrificed. In neither group did the survival rate or tumour incidence differ from untreated mice of the same strains (Mellon Institute, 1958). Rat. Groups of 10 rats (5 of each sex) were fed 1500 or 2250 ppm carbaryl in the diet for 96 days. At 2250 ppm, decreased body-weight in the females, increased liver weight in the males and increased kidney weight in the females were observed, while at 1500 ppm there was increased kidney weight in the females. A minor histopathological change in the form of diffuse cloudy swelling of the kidney tubules was noted at the higher concentration (Carpenter et al., 1961). Reproduction studies in 3 generations of CFE rats fed diets containing carbaryl adjusted to dose levels of 0, 0.0025 or 0.01 mg/kg body-weight daily, did not show any significant differences between treatment groups in fertility, gestation, lactation or viability of pups, mean number of pups per litter, body-weight of pups at weaning or teratology (Mellon Institute, 1965). Guinea-pig. Male guinea-pigs were injected with carbaryl and after a 3-week period were given a challenge dose. There was no evidence of development of sensitization (Carpenter et al., 1961). Dog. Groups of 3 or 4 dogs were given doses of 0.45, 1.8 and 7.2 mg/kg body-weight/day by capsule, 5 days per week for 1 year. Diffuse cloudy swelling of the kidney tubules was found in all the dogs at the 7.2 mg/kg level. Focal cloudy swelling was found in the controls. One female at the 0.45 mg/kg level had transient hind-leg weakness, but no histological lesion was found at necropsy (Carpenter et al., 1961). Long-term studies Mouse. Groups of 48 male and 48 female Cd-1 mice were given 0, 100 and 400 ppm or carbaryl in the diet. After 80 weeks, 12 survivors of each sex from each group were sacrificed. Survival rate, pathology and tumour incidence were comparable in all groups (Mellon Institute, 1963) Rat. In a 2-year experiment, groups of 20 CF-N rats of each sex were given diets containing 0, 50, 100, 200 and 400 ppm of carbaryl. After 6, 9 and 12 months, 4, 6, or 8 rats of each sex were killed for organ weight comparison and histopathological examination. The remainder were sacrificed after 2 years. The highest dose level produced cloudy swelling of the kidney tubules after 1 year and cloudy swelling of the central hepatic cords in the males after 2 years. Terminal body-weight in the males at the high level was reduced. There were no effects at the lower dose levels (Carpenter et al., 1961). Comments While teratogenicity studies using extremely low doses were negative in the rat, studies in other species have not been reported but would be very desirable. Several carbaryl metabolites have been identified in animals but not yet in plants. Excretion of carbaryl and its metabolites appears to be rapid in animals. Studies on the identification and toxicological evaluation of residues occurring in plants would be desirable. The behavioural studies appear interesting in relation to the mode of action and as a potential system for detection of toxicity. However, no data are available concerning experiments with continuous exposure to the compound. TOXICOLOGICAL EVALUATION Level causing no toxicological effect Mouse: 400 ppm in the diet, equivalent to 60 mg/kg/day Rat: 200 ppm in the diet, equivalent to 10 mg/kg/day Dog: 1.8 mg/kg/day Estimate of acceptable daily intake for man 0-0.02 mg/kg per day. (This value is based on experiments carried out with carbaryl, and thus does not take account of chemical alterations of the pesticide brought about by the plants to which it has been applied.) RESIDUES IN FOOD AND THEIR EVALUATION Use pattern (a) Pre-harvest treatments Carbaryl has been approved for use on a wide variety of food crops, including cereals, fruits and vegetables in a number of countries. It is being used in increasing amounts and is partly replacing more persistent and toxic compounds. In some countries it is used against external parasites of cattle. It is suggested for the control of at least 10 insects which attack cane fruit (berries), 20 which attack tree fruits, 25 which attack vegetables, as well as for use on other commodities and livestock. The usual rate of application for berries and vegetables is 1 or 2 lb per acre but for tree fruits as high as 10 lb per acre is suggested. (b) Post-harvest treatments Carbaryl has been used experimentally on stored cereals but is not so used on a commercial scale. National tolerances Country Product Parts per million Austria General 10 Canada Various 5, 10 and 25 United States of Sorghum (grain) 10 America Rice 5 Various fruits, cabbage, lettuce, carrots 10 Fruits (cane) 12 Garden beet, parsnips, radishes 5 Residues resulting from supervised trials Many data have been obtained from supervised trials on a large number of food crops produced under varying cultural conditions, rates and times of application, pre-harvest intervals, etc. This information is too extensive to reproduce in this monograph. Table 1 therefore contains estimates of residues for groups of commodities as contained in these reports. (A file summarizing such data for ca. 85 crops is held at the FAO headquarters in Rome.) The residue figures quoted are those likely to be present as two different pre-harvest intervals following uses at rates of application that are considered to be useful. Residues in food moving in commerce About two thousand samples of domestic and imported food products were examined by the United States Food and Drug Administration during 1966. Less than 10 per cent were found to contain residues of carbaryl and less than 0.1 per cent had residues above the tolerance levels (information from United States Food and Drug Administration). TABLE 1. AVERAGE RESIDUES FROM GOOD AGRICULTURAL PRACTICE Food Resulting residue Type Pre-harvest ppm period (days) Vegetables Leaf - spinach 14 10 Lettuce 30 1 Other 2 10 7-10 1 Cereal and 35-50 0 cereal products wheat, rye, oats Rice 14 5 30 1 Tree fruits 1 10 14-20 1 Caneberries 7 10 20 1 TABLE 1. AVERAGE RESIDUES FROM GOOD AGRICULTURAL PRACTICE Food Resulting residue Type Pre-harvest ppm period (days) Citrus 1 10 20-60 1 Shelled nuts 1 1 Fate of residues In the earlier studies on residues of carbaryl (Bibliography by Moorefield, 1966), consideration had been given to the parent compound carbaryl and its hydrolytic product, 1-naphthol. Residue studies on many crops showed that the quantity of 1-naphthol was small and difficult to separate from carbaryl. Thus, it was considered that 1-naphthol need not be measured separately from carbaryl. The United States of America tolerances for carbaryl are based on the assumption that the major part of the residue is the intact carbamate. Since the establishment of the initial tolerances for carbaryl, work has been done which may have some bearing on the quantative and qualitative aspects of the residue. Light, including artificial and sunlight, changes carbaryl. Carbaryl in the formulated state slowly degraded under the influence of ultra-violet and to give several unidentified products (Okada et al., 1961). Crosby et al. (1965) reported that ethanol or hexane solutions of some methylcarbamate insecticides, including carbaryl, gave a variety of cholinesterase-inhibiting derivatives when exposed to either artificial or sunlight. The products were separated but not identified. Abdel-Waheb (1966) reported that the nature of (1) the surface, (2) the light, and (3) the compound affected the rate of conversion of carbaryl and other carbamates in vitro in the solid state. Since neither the qualitative nor quantative aspects of photo-decomposition of carbamates have been established, the significance of these studies in relation to current and future tolerances for carbaryl must await further study. (a) In animals Whitehurst et al. (1963) using the colorimetric method of analysis sensitive to carbaryl, 1-naphthol and 1-naphthol conjugates concluded that, when cows were fed on a diet containing carbaryl, no residues, to the limit of method, were found in the milk. This was confirmation of the feeding study by Gyrisco et al. (1960), who fed dairy cows carbaryl at levels of up to 450 ppm. In another study, carbaryl was dusted and sprayed on cows. No detectable residues were found in milk when carbaryl was dusted on to animals, but after 48 hours some carbaryl residues were found in the milk when the spray application was used (Buttram, 1964; Camp et al., 1963). In recent work done by Dorough (1966), ring-labelled carbaryl was fed to a lactating cow. A total of approximately 1 ppm, based upon a radioactivity measurement calculated as carbaryl, was found in the skim milk six to 12 hours after administration of 3.05 mg/kg body-weight. Approximately one half of this residue was chloroform extractable, and one half was water extractable with a small unextractable fraction. At the end of 60 hours all the radioactivity (calculated to be 0.01 ppm as equivalents of carbaryl) was unextractable from the milk. In the six-hour samples about 30 per cent of the radioactivity in the milk was characterized as 5,6-dihydro-5,6-dihydroxy 1-naphthol N-methylcarbamate, and approximately 20 per cent was an unknown metabolite. Neither of these materials, corresponding to 50 per cent of the total milk residue (0.5 ppm), responded to the standard colorimetric method commonly used for carbaryl. Cattle, sheep, goats, and hogs were sprayed four times in two weeks with a 1.0 per cent suspension of carbaryl and Hereford steers were fed 200 ppm of carbaryl in the diet for a 27-day period. These animals were slaughtered at one and seven days after spraying or at the end of the feeding interval. Residues of carbaryl, 1-naphthol and conjugates of 1-naphthol were not detected in the body tissues of any of the cattle, sheep, or hogs seven days after spraying. At this time interval some small residues were noted in the fat and brain of a goat. No residues were detected in tissues of cattle fed carbaryl for 27 days (Claborn, 1963). Krishna & Casida (1966) have reported that less than 10 per cent of the administered acute dose of carbonyl-C14-carbaryl was recovered after 48 hours as tissue residues, primarily in those tissues known to be involved in body contaminant eliminations - (e.g. liver, spleen, kidney). After seven days Knaak (1966) found no residues resulting from carbonyl-carbaryl. Laying hens were dusted three times at four-day intervals using 4 gm of five per cent carbaryl per bird. One day after treatment no residues were found in each type of edible tissue except skin. Seven days after treatment this residue was reduced to low levels. Eggs were found to be free of residue, throughout the study (Johnson, Critchfield & Arthur, 1963). (b) In plants A limited amount of metabolism studies on carbamates in and on plants has been reported. Studies by Dorough et al. (1963, 1964) found that radioactive carbaryl yielded water soluble persistent metabolites which were different than those found in the milk of a goat. Carbonyl-C14-carbaryl, injected and administered to the surface of bean plants yielded compounds that largely remain within the plant. While these compounds have not been characterized, they are stable and after 12 hours are not extractable by the usual organic solvents. Abdel-Wahab observed that approximately 50 per cent of the surface administered dose of C14 radioactivity was recovered after 72 hours. When bean plants were injected into the stem with radioactive carbaryl, approximately 75 per cent of the radioactivity persisted for at least six days as aqueous and unextractable materials. Thus, reactions within the plant presumably produce carbamates in some stable form. These non-hydrolytic metabolites in many instances may not respond to the usual method of analysis for carbaryl because (1) the metabolites yield a phenolic material different than 1-naphthol and do not show the same colour reaction, and (2) the major fraction of some of the metabolites show solubility properties different than the parent compounds. Preliminary studies on bio-assay of certain metabolites have indicated a reduced biological activity when compared with the parent compounds. (c) In storage and processing Raw unwashed tomatoes, harvested from field treated applications, were stored at 55° F for approximately two weeks with samples taken at varying intervals. Data showed that no loss of carbaryl was realized under these storage conditions. The harvested tomatoes were subjected to home and commercial canning operations, and analysis of samples indicated that 50 per cent or more of the residue was removed by water-washing and nearly complete removal of all residue was realized by peeling and canning operations (Farrow et al. 1966). Methods of residue analysis The methods available for carbaryl are based on a colorimetric determination following suitable extraction and clean-up. There are approximately 20 variations of the basic method for different types of food products, most of which are not published and no one method has been tested for all food products. For most fruits and vegetables the methods of (1) AOAC or that of (2) Benson & Finocchiaro (1965) are suggested. These methods have a sensitivity of about 0.1 ppm. The above methods do not give very adequate clean-up for citrus, olives, shelled nuts, many cereals and cereal products. Of the many variations of the method, that developed for wheat and wheat fractions has the most comprehensive clean-up. It is believed that it would be useful for all products not amenable to the AOAC method. RECOMMENDATIONS FOR TOLERANCES The low acceptable daily intake necessitated a very close evaluation of residue data to determine tolerances which would permit useful applications to crops without possibly providing residues which might exceed the acceptable daily intake. Some data indicate that there will be losses under some conditions of storage and processing. However, not enough data are available to make a calculation at present, therefore no factor for such losses are included in the calculations. The basic factor used in recommending temporary tolerances which yield values within the ADI is that of choosing a long pre-harvest interval. The recommended tolerance figures are indicated in the following table. TEMPORARY TOLERANCE RECOMMENDATIONS FOR CARBARYL Crop Temporary tolerance in ppm Vegetables 1.0 Cereal and cereal products 1.0 Tree fruits 1.0 Caneberries 1.2 Citrus 10.0 Shelled nuts 1.0 Further work or information In the above calculations no considerations were given to possible losses during storage, shipping and processing. It is recommended that such data be developed and made available to the working party. It is also recommended that further work be done to establish more definitely the character of the terminal residue in treated plants. REFERENCES PERTINENT TO BIOLOGICAL DATA Baron, R. L., Casterline, J. L. & Fitzhugh, O. G. (1964) Toxicol. appl. Pharmacol., 6, 402 Best, E. M., jr & Murray, B. L. (1962) J. occup. Med., 4, 507 Carpenter, C. P., Weil, C. S., Palm, P. E., Woodside, M. W., Nair, J. H. & Smyth, H. F., jr (1961) J. Agr. Food Chem., 9, 30 Claborn, H. V., Roberts, R. H., Mann, H. D., Bowman, M. C., Ivey, M. C., Weidenbach, C. P. & Radeleff, R. D. (1963) J. Agr. Food Chem., 11, 74 Dorough, H. W., Leeling, N. C. & Casida, J. E. (1963) Science, 140, 170 Dorough, H. W. & Casida, J. E. (1964) J. Agr. Food Chem., 12, 294 Eheart, J. F., Turner, E. C. & Dickinson, J. (1962) J. Econ. Ent., 55, 504 Gaines, T. B. (1960) Toxicol. appl. Pharmacol., 2, 88 Goldberg, M. E. & Johnson, H. E. (1964a) J. Pharm. Pharmacol., 16, 60 Goldberg, M. E. & Johnson, H. E. (1964b) J. Pharmacol. exp. Ther., 145, 367 Goldberg, M. E., Johnson, H. E. & Knaak, J. B. (1965a) Psychopharmacologia, 7, 72 Goldberg, M. E., Johnson, H. E. & Knaak, J. B. (1965b) Biochem. Pharmacol., 13, 1483 Gyrisco, G. G., Lisk, D. J., Fertig, S. N., Huddleston, E. W., Fox, F. H., Holland, R. F. & Trimberger, G. W. (1960) J. Agr. Food Chem., 8, 409 Johnson, D. P., Critchfield, F. E. & Arthur, B. W. (1963) J. Agr. Food Chem., 11, 77 Knaak, J. B., Tallant, M. J., Bartley, W. J. & Sullivan, L. J. (1965) J. Agr. Food Chem., 13, 537 Krishna, J. G. & Casida, J. E. (1966), J. Agr. Food Chem., 14, 98 Mellon Institute of Industrial Research (1958a) Unpublished Report Mellon Institute of Industrial Research (1958b) Unpublished Report Mellon Institute of Industrial Research (1963) Unpublished Report Mellon Institute of Industrial Research (1965) Unpublished Report Roberts, R. H., Jackson, J. B., Westlake, W. E., Ackerman, A. J. & Claborn, H. V. (1960) J. Econ. Ent., 53, 326 REFERENCES PERTINENT TO AGRICULTURAL DATA Abdel-Wahab, A. M., Kuhr, R. J., and Casida, J. E. (1966) The fate of C14 C=O labeled aryl methylcarbamate insecticide chemicals in and on bean plants. J. Agr. Food Chem. 14:290. AOAC (1965) Methods of Analysis, (10th edition) paras. 24. 188-24.192 Benson, W. R. and Finocchiaro, J. M. (1965) Rapid Procedure for Carbaryl Residues: Modification of Official Colorimetric Method. J. Assoc. Offic. Agric. Chem. 48, 676-679 Buttram, J. Ress. (1964) Thesis, Auburn University. The metabolism of carbamate and organophosphate insecticides by cattle and poultry and associated residues in livestock products. Camp, H. B., Buttram, J. R., Hays, K. L., and Arthur, B. W. (1963) Sevin residues in milk from dairy cows following dermal applications. J. Econ. Entomol. 56:402-404. Casida, J. E., and Augustinsson, K.-B. (1959) Reaction of Plasma Albumin with 1-naphthyl N-methylcarbamate and certain other esters. Biochem. Biophys. Acta. 36:411-26. Casida, J. E., Augustinsson, K.-B. and Jonsson, G. (1960) Stability, toxicity and reaction mechanism with esterases of certain carbamate insecticides. J. Econ. Entomol. 53:205-12. Claborn, H. V. (1963) Residues in body tissues of livestock sprayed with Sevin or Sevin in the diet. J. Agr. Food Chem. 11:74-76. Crosby, D. C., Leitus, E., and Winterlin, W. L. (1965) The photodecomposition of carbamate insecticides. J. Agr. Food Chem. 13:204. Dorough, H. W., Leeling, N. C. and Casida, J. E. (1963) Nonhydrolytic pathway in metabolism of N-methylcarbamate insecticides. Science 140:170-171. Dorough, H. W. and Casida, J. E, (1964) Nature of certain carbamate metabolites of the insecticide Sevin. J. Agr. Food Chem. 12 (4): 294-304. Dorough, H. W. (1966) Carbaryl-C14 metabolism in a lactating cow. Private communication and in press. Farrow, R. P., Lamb, F., Cook, R. W., Bergmans, B., Kimball, J. and Elkins, E. R. (1966) Removal of Sevin residues from tomatoes during commercial and home preparative procedures. Paper # 36, Pesticides Subdivision of Agr. and Food Div., Amer. Chem. Soc. 152nd Meeting, September 12-16, 1966. Gyrisco, G. G., Lisk, D. J., Fertig, S. N., Huddleston, E. W., Fox, F. H., Holland, R. F., and Trimberger, G. W. (1960) The effects of feeding high levels of Sevin on residue, flavor and odor of the milk of dairy cattle. J. Agr. Food Chem. 8:409-410. Hodgson, E. and Casida, J. E. (1960) Biological oxidation of N,N-dialkyl carbamates. Biochem. Biophys. Acta. 42:184-186 Hodgson, E. and Casida, J. E. (1961) Metabolism of N,N-dialkyl carbamates and related compounds by rat liver. Biochem. Pharmacol. 8:179-191. Johnson, D. P., Critchfield, F. E., and Arthur, B. W. (1963) Determination of Sevin insecticide and its metabolites in poultry tissues and eggs. J. Agr. Food Chem. 11:77-80. Knaak, J. B., Tallant, M. J., Bartley, W. J., and Sullivan, L. J. (1965) The metabolism of carbaryl in the rat, guinea pig and man. J. Agr. Food Chem. 13:537-543. Krishna, J. G. and Casida, J. E. (1966) Fate in Rats of the Radiocarbon from ten variously labeled methyl- and dimethylcarbamate-C14 insecticide chemicals and their hydrolysis products. J. Agr. Food Chem. 14:98-105. Leeling, N. C. and Casida, J. E. (1966) Metabolites of carbaryl in mammals and enzymatic systems for their formation. J. Agr. Food Chem. 14:282-290. Morefield, H. H. "Agr. Products Tech. Service Report" bibliography on Sevin insecticides (carbaryl) containing 1463 references has been compiled by the Union Carbide Corporation, R & D Dept., Agr. Products, Olefins Division, P.O. Box 8361, So. Charleston, W. Virginia 25303. Okada, K., Nomura, K., Yamamoto, S., (1961) (no title). Nippon Nogaikagaku Kaishi 35:739. Whitehurst, W. E., Bishop, E. T., Critchfield, F. E., Gyrisco, G. G., Huddleston, E. W., Arnold, H., and Lisk, D. J. (1963) The metabolism of Sevin in dairy cows. J. Agr. Food Chem 11:167-169. Williams, R. T. (1959) Detoxication Mechanisms. John Wiley & Sons, Inc., N. Y. 796 p.
See Also: Toxicological Abbreviations Carbaryl (EHC 153, 1994) Carbaryl (HSG 78, 1993) Carbaryl (ICSC) Carbaryl (PIM 147) Carbaryl (FAO Meeting Report PL/1965/10/1) Carbaryl (FAO/PL:1967/M/11/1) Carbaryl (FAO/PL:1968/M/9/1) Carbaryl (FAO/PL:1969/M/17/1) Carbaryl (AGP:1970/M/12/1) Carbaryl (WHO Pesticide Residues Series 3) Carbaryl (WHO Pesticide Residues Series 5) Carbaryl (Pesticide residues in food: 1976 evaluations) Carbaryl (Pesticide residues in food: 1977 evaluations) Carbaryl (Pesticide residues in food: 1979 evaluations) Carbaryl (Pesticide residues in food: 1984 evaluations) Carbaryl (Pesticide residues in food: 1996 evaluations Part II Toxicological) Carbaryl (JMPR Evaluations 2001 Part II Toxicological) Carbaryl (IARC Summary & Evaluation, Volume 12, 1976)