TECNAZENE      JMPR 1978


         Limited available information was reviewed in 1974 (FAO/WHO,
    1975) but the meeting reported that before an ADI or residue limits
    could be recommended the following data were required.

         1.   Adequate toxicological data.

         2.   Full information on specifications for the chemical and the
              formulated products (including impurities,
              e.g., HCB), present use patterns, residue data
              from supervised trials, fate of residues in
              crops other than potatoes and in soils, etc.

         The data received in response to these published requirements
    are evaluated in this monograph.


    Chemical name



         2,3,5,6-Tetrachloronitrobenzene, TCNB, FusarexR, FumiteR,
    Folosan DB 905.

    Structural formula


    Other information on identity and properties

    Molecular weight:             261

    Physical state:               Colourless, odourless, crystalline solid

    Melting point:                99°C

    Volatility:                   Appreciably volatile at room temperature

    Solubility:                   Practically insoluble in water; soluble
                                  in ethanol; readily soluble in acetone,
                                  benzene, carbon disulphide, chloroform,

    Stability:                    Generally very stable; can be dispersed
                                  by pyrotechnic mixtures. Decomposes
                                  slowly in solution when irradiated with
                                  ultra-violet light.

    Purity of technical material: The test material was more then 99% pure
                                  and contained less than 0-1% of
                                  hexachlorobenzene. Full information was
                                  available to the Meetings.




         One of the major metabolites identified in the urine following
    oral administration of 1-3 g of 2,3,5,6-tetra-chloronitrobenzene to
    rabbits was mercapturic acid, being excreted at a rate of 11%
    within 48 hours after application. Further metabolites excreted
    were an ether glucuronide (12%), 2,3,5,6-tetrachloroaniline (10%),
    unconjugated 4-amino-2,3,5,6-tetrachlorophenol (2%) and an etheral
    sulphate (1%) (Bray et al., 1953; Betts et al., 1955). Similar
    amounts of mercapturic acid were excreted in the urine of rats
    (Barnes et al., 1959).

         Rat liver contains an enzyme catalysing the formation of
    glutathione S-conjugates with replacement of the active halogen of
    aromatic compounds, known to be excreted as mercapturic acid.
    Evidence was presented by Al-Kassab et al., 1963, that the enzyme,
    that catalyses the displacement of halogen will also replace the
    labile nitro group of polychloronitrobenzenes with glutathione and
    of the carcinogen 4-nitroquinoline-N-oxide.

         Studies in pigeons showed that orally administered
    2,3,5,6-tetrachloronitrobenzene is also converted to mercapturic
    acid (Wit et al., 1969).


    Special studies on carcinogenicity

         Tests were performed to study the carcinogenic action of
    polychloronitrobenzenes, its tumour initiating activity and its

    action on carcinogenesis induced by benz(a) pyrene: one of the
    reasons for performing these tests was the similarity in
    biotransformation of TCNB and the carcinogenesis

         Skin application of 0.2 ml of 0.3% acetone solutions to 10
    males and 10 females twice weekly for 12 weeks was followed by
    croton oil treatment for 20 weeks. Controls (10 of each sex) were
    treated according the same schedule, instead of tecnazene only
    acetone was given in the first phase. By the end of the croton oil
    treatment, 41 papillomas had been observed in treated males and 13
    in treated females versus 7 and 5 in controls.

         Tecnazene (> 99% pure) was administered continuously in the
    diet to 65 male and 65 female CD-1 animals in each dose group at
    dietary levels of 09 750 and 1500 ppm for a period of 80 weeks. The
    treatment did not adversely affect the general condition,
    behavioural patterns, body weight gain and food intake. Survival in
    males was poorer in the controls than in treated groups; mice alive
    at 80 weeks were 16, 17 and 31 males and 27, 37 and 25 females at
    0, 750 and 1500 ppm respectively. Several macroscopic pathological
    alterations with increased incidences in the dose-groups were
    observed, but because no distinct dose-relationship is found, no
    biological significance could be attached to these changes. No
    dose-related group distribution of neoplasms was observed, with the
    only exception of a higher frequency of pulmonary adenoma in the
    male animals of the 1500 ppm group; 8 animals showing this lesion
    compared to 4 animals in the control and low dose group (Ben-Dyke
    et al., 1978b). Skin carcinogenesis by benzo(a)pyrene was not
    affect by TCNB (Searle, 1966).

         Groups of 65 male and 65 female rats were fed with a diet
    containing tecnazene (purity > 99%) at concentrations of 0, 750
    and 1500 ppm for a period of 104 weeks. The feeding did not affect
    general appearance, behaviour, mortality and food consumption. In
    all groups survival at 78 weeks was 50% or more. In the first half
    of the treatment period body-weights were unaffected, whereas in
    the second half a slight reduction of body weights was observed in
    treated males at 1500 ppm. The macropathological findings and 
    non-neoplastic histologic changes were those commonly found in the 
    rat strain used; they were not considered to be treatment-related and
    did not show clear dose-relationships. Liver hyperplastic nodules
    were seen in one female at 750 ppm and in 3 males and 2 females at
    1500 ppm. Benign or malignant tumours of the mammary glands were
    seen in 39 females of the control group versus 48 females given 750
    ppm and 50 animals given 1500 ppm. Adenocarcinomas were found in 4
    females of the control group compared to 5 and 8 females at the 750
    and 1500 ppm level respectively. These differences are of
    borderline statistical significance (p approx. 0.05). Only one
    liver-cell tumour was seen and this was in a control rat (Ben-Dyke
    et al., 1978a).

    Special studies on teratogenicity

         2,3,5,6-tetrachloronitrobenzene did not show embryotoxic or
    teratogenic properties when orally administered at doses of up to
    200 mg/kg b.w. to CD rats and C 57 B 1/6 mice on gestation day 7-18
    or to CD-1 mice on day 7-16 (Courtney et al., 1976).

    Acute toxicity

         The acute intraperitoneal LD50 of
    2,3,5,6-tetrachloronitrobenzene in the rat is approximately 3500
    mg/kg (Wit et al., 1960)

    Short Term Studies


         Groups of two pigs were maintained an a diet containing
    potatoes that have been treated with a dust-mixture of tecnazene at
    levels of 0, 60, 400 and 600 mg/lb potatoes for 26 weeks. The
    highest dose level of 600 mg/lb potatoes being ten times as high as
    that which will be used for the routine dressing of potatoes,
    corresponds to 7.1 g tecnazene per pig per day or approximately to
    50 mg/kg b.w. and caused reduction in body weight gains in the
    first half of the study. No other abnormal findings with respect to
    general health condition, haematological parameters or gross and
    microscopic examination of liver and kidney were detected. No
    methaemoglobinanaemia was produced by the treatment (Abrams et al.,


         In a 10 week-feeding study rats were maintained on a diet with
    2000 ppm tecnazene. No abnormalities in general health, blood
    picture, autopsy findings and histological picture of liver and
    kidney were detected. In the male animals increased liver- and
    testis-weights were observed (no other details described) (Wit et
    al., 1960).


         Following oral administration of tecnazene to rabbits the
    material absorbed is excreted mainly as an ether glucuronide,
    2,3,5,6-tetrachloraniline and mercapturic acid. The study of the
    biotransformation of some polychloronitrobenzenes in rats and
    rabbits showed that these compounds were converted to mercapturic
    acids; the formation of S-substituted glutathione by replacing the
    labile nitro groups with glutathione seems to be the first stage in
    mercapturic acid formation.

         An experiment on mice on skin carcinogenesis is suggestive of
    a tumour-initiating effect of tecnazene, but, a full evaluation is
    impaired by the small number of animals used.  The results of the 

    carcinogenicity tests with feeding of the test compound over 104
    weeks to rats and 80 weeks to mice gave no clear indication of a
    carcinogenic activity in tecnazene. The increased number of mammary
    tumours in female rats was of borderline statistical significance.
    In the study on mice the tumour incidence was not increased.

         In the 80 week study in mice with 750 and 1500 ppm tecnazene
    in the diet no treatment revealed effects were noted. In the two
    year study on rats with dose levels of 750 and 1500 ppm a slight
    reduction of weight gain occurred in the males of the high dose group.
    Tecnazene showed no teratogenic activity in mice. No studies
    relating to mutagenicity, effects an reproduction or metabolism in
    different mammalian species were made available since the last
    evaluation by the 1974 Meeting.

         In view of come uncertainties in regard to the carcinogenic
    potential of tecnazene and the lack of adequate reproduction data
    only a temporary ADI was allocated.


    Level causing no toxicological effect

              Rat:      750 ppm in the diet equivalent to 38 mg/kg bw

              Mouse:    1500 ppm in the diet equivalent to 200 mg/kg bw

              Dog:      15 mg/kg bw

    Estimate of temporary acceptable daily intake for man

              0 - 0.01 mg/kg bw



         Tecnazene is used on potatoes after harvest, as a 3% dust
    formulation at the rate of 10 1b product per ton,(4.5g product/kg),
    to reduce sprouting during storage. This recommendation produces a
    theoretical initial loading on the potatoes of 134 mg/kg. Tecnazene
    displays the additional merits of not inhibiting would healing in
    freshly-clamped potatoes and of controlling dry rot, Fusarium
    caeruleum (Brown, 1947; Reavill, 1954). Tecnazene is also used as
    a smoke generator formulation at 15 mg/m3 to control Botrytis
    spp. on tomatoes, lettuce, chrysanthemums and other ornamental
    plants, and as a dust in chicory (witloff) culture.


         When potatoes were treated at 4.5g kg with 3% tecnazene dust,
    stored for 4-5 months, commercially graded and transported, mean
    residues on the tubers were of the order of 2 mg/kg. Increasing the

    storage period to six months caused a farther reduction to
    approximately 1 mg/kg. The original concentration applied (134
    mg/kg) is reduced mainly by handling, both before and after
    storage, but losses by evaporation were shown to occur during
    storage. Washing reduced residues still further and no tecnazene
    was detected in the flesh of peeled potatoes (limit of
    determination approximately 0.1 mg/kg) (Wilson and Dawson, 1953).

         In a similar study (Bullock, 1973), when potatoes treated as
    above were stored commercially for 4-5 months, tecnazene residues
    on tubers with adhering soil were normally less than 10 mg/kg; the
    mean residue was approximately 3 mg/kg. Washing the potatoes
    reduced residues to below 1 mg/kg (mean approximately 0.4 mg/kg).

         Residue levels in stored potatoes treated with a 30% liquid
    tecnazene formulation by means of a fogging machine have been
    reported (Wheatley Chemical Co., 1978). Three application rates
    were chosen, giving the recommended rate of 15 mg a.i./kg and one
    half and twice this rate (i.e. 25, 50 and 100 ml/ton); results are
    shown in Table 1.

        TABLE 1. Residues of tecnazene in treated potatoes


                                  Tecnazene residue (mg/kg)
                             Day 1            Day 60            Day 100

    Application         Whole                 Whole         Whole
    rate (mg ai/kg)     tuber     skin        tuber         tuber       skin

    7.5                 6.4       76.8        4.05          1.0         7.6

    15                  13.2      151.8       6.8           2.6         24.2

    30                  23.3      276.0       17.3          3.1         41.0

         Data from trials usage of tecnazene on 7 samples of glasshouse
    grown lettuce in 1972 showed residues ranging from 1.3 to 2.2 mg/kg
    (mean 1.7 mg/kg) at 11-19 days after treatment (Race, 1978).

         Fodderbeets treated at 90 mg/kg with tecnazene and stored for
    five months contained residues of 0.1-13 mg/kg, with most samples
    containing less than 5 mg/kg tecnazene (Wit et al., 1960).

         In the culture of chicory (witloff) tecnazene can be used as a
    fungicidal powder on the roots when they are forced. Residues were
    determined in the sprouts, and in the remaining roots which are used
    as fodder, six weeks after treatment at 150 g product per m2 (4.5 g
    a.i. per m2). Residues in the sprouts did not exceed 0.05 mg/kg and
    in the roots were less than 3 mg/kg (Wit et al., 1960). Confirmatory
    studies at a 3 g m2 treatment rate showed residues not exceeding 0.11
    mg/kg in the sprouts and less than 0.3 mg/kg in the roots
    approximately seven weeks after treatment (Bullock, 1973).


    In plants

    As reviewed above, tecnazene residues on potatoes are readily lost by
    evaporation. Under commercial conditions the major losses occur by
    handling, both before and after storage, although some losses also
    occur during storage, Washing treated potatoes reduces residues
    significantly (Wilson and Dawson, 1953; Bullock, 1973). Limited
    evidence indicated that washing chicory (witloff) roots was much less
    effective in reducing the residue content (Netherlands, 1978),

    In soil

         Tecnazene was rapidly lost from a sandy soil; over 50% in two
    months and all but 2% in ten months. Volatility of tecnazene is likely
    to have been a major contributory factor. The rate of loss was similar
    from both sterile and non-sterile sandy soil and at 100 mg/kg in this
    soil tecnazene had no effect on respiration or nitrification (Caseley,
    1968: Caseley and Broadbent, 1968).


         Washing, peeling and cooking potatoes all cause considerable
    reductions in tecnazene residue levels. As stated above, when potatoes
    treated at 4.5 g kg with 3% tecnazene dust were stored commercially
    for 4-5 months, mean tecnazene residues on tubers with adhering soil
    were approximately 3 mg/kg. Washing the potatoes reduced residues to
    below 1 mg/kg (mean approximately 0.4 mg/kg). After peeling, residues
    in uncooked edible flesh were normally below 0.1 mg/kg (mean
    approximately 0.04 mg/kg) (Bullock, 1973), Boiling reduces the level
    of tecnazene in peeled edible flesh by 50% or more (Bullock, 1973;
    Dalzeil and Duncan, 1974). Although baking unpeeled potatoes caused a
    slight increase in residues in edible flesh (up to two-fold), it
    caused a major reduction of tecnazene levels in peel and an overall
    reduction in the residue level in the potato (Bullock, 1973).

         Potatoes grown in the U.K. in 1976 and 1977 were purchased on the
    market and examined for residues of tecnazene. In addition to the
    whole tubers analysed from both crops, some samples from the 1977 crop
    were washed and peeled before analysis. Results obtained are shown in
    Table 2. Although most results on whole tubers were below 10 mg/kg, an

    appreciable number were greater than 5 mg/kg in both years (Anon,

        TABLE 2. Residues of tecnazene in marketed potatoes


    Year      Commodity             No. of       Tecnazene residue (mg/kg)

                                                 Range              Mean

    1976      Whole tubers          3            10.5 - 19.3        15.3

              Whole tubers          13           3.0 - 9.0          5.7

              Whole tubers          7            0.6 - 1.5          1.1

    1977      Whole tubers          17           2.2 - 7.6          4.6

              Whole tubers          26           <0.1 - 1.7         0.3

              Washed and peeled
              tubers                19           <0.1 - 0.25        <0.1
         Over a 10 year period (June 1964 - August 1974), about 300
    samples of potatoes were collected during a series of market basket
    surveys in the USA. Of these 14 were found to contain detectable
    residues of tecnazene, ie 0.001 mg/kg or above; the highest level
    found was 0.37 mg/kg, Over 3500 samples of other foodstuffs were also
    analysed in which trace residues (0.01 mg/kg or less) were reported in
    15 samples representing a wide range of foodstuffs (Corneliussen,
    1969, 1970, 1972; Duggan et al., 1966, 1967; Johnson and Manske 1975;
    Manske and Corneliussen, 1974; Manske and Johnson, 1975, 1977; Martin
    and Duggan, 1968).

         Of 60 samples of lettuce examined in Belgium in 1972, 52
    contained less than 0.01 mg/kg and only one contained more than 2
    mg/kg of tecnazene. Similarly, of 54 samples of chicory examined, only
    two contained more than 0.01 mg/kg but none more than 2 mg/kg
    (Valange, 1974). No tecnazene was detected in 17 samples of maize, and
    only one of 23 samples of dried sugar beet pulp contained a detectable
    residue of 0.03 mg/kg (Valange and Henriet, 1974). A survey of canned
    peas, haricot beans, carrots, celery, salsify, asparagus and cherries
    in Belgium showed no residues of tecnazene above 0.001 mg/kg (Biston
    et al., 1975).

         Westöö and Noren (1973) examined about 2500 samples of fresh and
    canned, home grown and imported foods in Sweden during the period 1968
    to June 1972. Of the foods analysed, detectable residues of tecnazene
    appeared most commonly in lettuces; of 230 samples tested 15 contained
    0.02 to 0.1 mg/kg, 14 contained 0.11 to 0.5 mg/kg and 9 contained 0.51
    to 1.4 mg/kg of tecnazene. A few samples of carrots (6 of 140),
    tomatoes (3/240), paprika (1/65) and parsley (4/13) had residues of
    tecnazene in the range 0.02 to 0.1 mg/kg.

         Similar studies in Sweden in 1976-77 showed no residues of
    tecnazene above 0.1 mg/kg in mushrooms (9 samples), carrots (187),
    sweet peppers (166), parsley (16), beetroots (4) tomatoes (467) or
    apples (931). Of 253 samples of potatoes, 2 were in the range 0.11 to
    0.5 mg/kg, 2 from 0.51 to 1.0 mg/kg and 4 between 1.1 and 5.0 mg/kg
    (Sweden, 1973).


         Gas chromatography with an electron-capture detector is the
    preferred method of residue analysis. Crop samples are macerated with
    light petroleum, dried and filtered, and an aliquot is injected into
    the gas chromatograph. The limit of determination is 0.01 mg/kg or
    better. Recoveries in excess of 90% are normally obtained from
    potatoes and chicory, for which the method is suitable for use as a
    regulatory method. Confirmation of the residue can be obtained by
    clean-up of the extract by thin-layer chromatography and further gas
    chromatographic determination (Bullock, 1973).

         The use of gas chromatography with a flame ionisation detector
    has also been reported. Tecnazene residues could be determined in
    hexane extracts applied directly to the gas chromatograph; however,
    the accumulation of charred plant residues on the column and overlap
    with natural components using this detector limited the value of this
    approach. Solvent partition and an alumina column were used
    successfully to clean-up the extracts and a method of avoiding the
    formation or troublesome emulsions has been described (Dalziel and
    Duncan, 1974).

         Polarographic and colorimetric methods have also been described
    (Webster and Dawson, 1952; Auerbach, 1950; Canbäck and Zajaczkowska
    1950; Higgons and Toms, 1957).


    National MRLs reported to the meeting are shown in Table 3.

    TABLE 3. National MRLs for tecnazene reported to the meeting

    Country             Commodity                          MRL (mg/kg)

    Belgium             Vegetables and strawberries        2

    Federal Republic    Strawberries, chicory, lettuce,
    of Germany          tomatoes                           0.03

                        Other vegetables                   0.05

    Netherlands         Vegetables and strawberries        2

    United States       Potatoes
    of America                                             25

    Zambia              Potatoes                           25


         Tecnazene is used on potatoes as a post-harvest sprout
    suppressant and as a fungicide on chicory (witloof) and glasshouse
    grown tomatoes and lettuce. Residue data were available from
    supervised trials on potatoes, lettuce and chicory (witloof). Some
    data from marketed samples, and market basket surveys showed
    detectable residues in potatoes and, occasionally, in other crops such
    as lettuce, tomatoes, carrots, etc. No information was forthcoming on
    the fate of residues in crops other than potatoes. Information
    concerning the purity specification for the technical material was
    available and acceptable to the Meeting; the content of
    hexachlorobenzene in this material was below 0.1%. Sufficient data
    were available to allow the following recommendations to be made for
    temporary maximum residue limits in certain crops. Gas chromatographic
    methods of analysis are available and suitable for regulatory


         The following temporary maximum residue limits apply to

              Commodity                          Temporary MRL, mg/kg

              Lettuce                            2
              Potatoes (washed before analysis)  1
              Chicory (witloof)                  0.2
              Other vegetables                   0.1
              Tomatoes                           0.1


    Required (by 1981)

    1.   Clarification of the tumour initiating activity observed in a
    skin painting experiment on mice.

    2.   Adequate study on reproduction.


    1.   Short-term tests on mutagenicity.

    2.   Metabolism in different mammalian species.

    3.   Information regarding levels of residues occurring in meat and
    milk resulting from consumption of treated chicory roots or potatoes
    by cattle.


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    Al-Kasseb, S., Boyland, E. and Williams, K. An enzyme from rat
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    Anon. Residues of tecnazene on market samples of potatoes. Data
    (1978)              from the Food Research Institute. Norwich, UK

    Auerbach, M.E. Colorimetric estimation of tetrachloronitrobenzene.
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    Ben-Dyke, R., McSheehy. T.W., Cummins, H.A., Finn, J.P. and Newman,
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    Ben-Dyke, R., McSheehy, T.W., Cummins, H.A., Finn, J.P. and Newman,
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                        continuous dietary administration for 80 weeks.

                        Unpublished report of the Life Science Research,
                        No. 78/ILY 19/080, submitted by ICI Ltd.

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    (1955)              pentachloronitrobenzene and 
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                        laboratory-treated and in commercial samples of
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    Martin, R.J. and Duggan, R.E. Pesticide residues in total diet
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    Netherlands Residues of tecnazene in various crops. Unpublished data.

    Race, J. Residues of tecnazene in green-house lettuce (1972). Data
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    Reavill, M.J. Effect of certain chloronitrobenzenes on germination,
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    Searle, C.E. Tumour initiatory activity of some chloromonitrobenzenes
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    (1952)              estimation of tetrachloronitrobenzene residues on
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    See Also:
       Toxicological Abbreviations
       Tecnazene (EHC 42, 1984)
       Tecnazene (HSG 12, 1988)
       Tecnazene (WHO Pesticide Residues Series 4)
       Tecnazene (Pesticide residues in food: 1981 evaluations)
       Tecnazene (Pesticide residues in food: 1994 evaluations Part II Toxicology)