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    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.

    Formula

    CHEMICAL STRUCTURE 

    BIOLOGICAL 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 g 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)