QUINTOZENE JMPR 1973 Explanation This soil fungicide was evaluated at the 1969 Joint Meeting (FAO/WHO, 1970). A temporary acceptable daily intake of 0-0.001 mg/kg bw was established with the requirement that the results If carcinogenicity studies on two species of animal should be made available by June 1973. Studies to explain the cause of growth depression and the effects on bone marrow and liver in dogs and studies on the metabolism of quintozene and on the activity of the metabolites, particularly pentachloroaniline were requested. It is noted that most recent studies on this fungicide have given emphasis not only to quintozene per se, but also to some related chemical substances and impurities, which may be present in the technical product, especially hexachlorobenzene. Further data made available are summarized in this monograph addendum. EVALUATION FOR ACCEPTABLE DAILY INTAKE Biochemical aspects Absorption, distribution and excretion Groups of three cows were administered quintozene orally at dosage levels equivalent to 0, 0.1, 1 and 10 ppm in the diet for 12-16 weeks. One cow received 1000 ppm for one month. Milk, biopsy and autopsy samples of fat and autopsy samples of other tissues were analysed. The results of the analyses using a highly sensitive method demonstrated that tissue storage of quintozene and the principal metabolites did not occur, nor were they excreted in milk (Borzelleca et al., 1971). No quintozene, pentachloroaniline or methyl pentachlorophenol sulphide were detected in milk from a cow administered quintozene orally at a level equivalent to 5 ppm in the diet for three days. Forty-five per cent. of the administered dose was eliminated as pentachloroaniline within four days of the last dose (St. John et al., 1965). Quintozene was administered orally to mice as a solution in corn oil/acetone mixture. Only low serum quintozene levels (< 1 ppm) were found, the highest levels being found two to six hours after dosing. Analysis of tissues after single or multiple doses of quintozene showed that the highest concentrations occurred two to six hours after dosage but these fell rapidly. Pentachloroaniline was also found but the highest concentration of this occurred in bile; this possibly accounts for the high concentration of this metabolite in faeces. Methyl pentachlorophenol sulfide was also found in tissues and the high concentration in liver two hours after dosage suggests that quintozene is rapidly converted to this metabolite, which is then rapidly excreted. Quintozene and its metabolites did not build up in tissues on repeated dosage. No data were presented on the hexachlorobenzene content of tissues. In pregnant mice more methyl pentachlorophenol sulfide passed the placenta than the other compounds and high concentrations were found in the fetus and uterus (Courtney, 1973). Biodegradation The major metabolite of quintozene in mice is pentachloroaniline. After repeated dosage the urinary content of this increases in male but not in female animals. Methyl pentachlorophenol sulfide is excreted mainly in the conjugated form (Courtney, 1973). TOXICOLOGICAL STUDIES Special studies on carcinogenicity A group of 10 male and 10 female mice was painted twice weekly for 12 weeks with an 0.3% solution of quintozene in acetone. A similar group of control animals was painted with acetone. All mice were then painted with croton oil for 20 weeks and surviving mice were killed after a further 20 weeks without treatment. Papillomata appeared in test animals after five to eight weeks treatment with croton oil and became more numerous until 5-10 weeks after cessation of treatment, after which some of them regressed. One test animal was found to have a single squamous cell carcinoma at the end of the experiment (Searle, 1966). Special studies on teratogenicity An unstated number of C57 black/6 mice received up to 500 mg/kg/day quintozene (containing 1% hexachlorobenzene) in 0.1 ml of oil on days 7-11 of gestation and were killed and examined on day 19. Fetal weight and mortality were unaffected but the incidence of eye abnormalities which normally affect 107 of young was increased. In addition there was a 49% increase in renal agenesis and cleft palates occurred in some litters from treated mothers. Dosage levels of 100 and 200 mg/kg/day were without ill-effect. Quintozene in corn oil/acetone was administered to an unstated number of random bred CH1 mice from day 7-17 of gestation. Fetal mortality was unaffected at the 200 mg/kg dosage level but animals receiving 500 mg/kg produced young with a high incidence of cleft palate; kidney abnormalities were not found. An unstated dose of quintozene of 99% purity was administered orally each day to random bred CB rats from days 7-18 of gestation. Animals were killed on the nineteenth day. No effect on maternal weight, liver weight, weight of fetuses, fetal viability and morphological development was seen (Courtney, 1973). Groups of at least 20 pregnant Charles River rats were administered orally by gavage 8, 20, 50 or 125 mg/kg of quintozene dissolved in corn oil once daily on days 6-15 of gestation. Negative control groups received corn oil or were intubated without being administered vehicle and a positive control group received chlorcyclizine. No abnormalities were found which could be attributed to quintozene treatment in the numbers of corpora lutea, implantations, dead and resorbed fetuses, viable fetuses, fetal weights and sex or in skeletal or soft tissue malformations (Jordan and Borzelleca, 1973). Special studies on metabolites An unstated number of C57 black/6 mice received up to 500 mg pentachloroaniline/kg in 0.1 ml oil on days 7-18 of gestation and were killed and examined on day 19. Maternal weight was decreased and fetal mortality increased at the 100 mg/kg dosage level but not at higher levels. Pentachloroaniline in corn oil/acetone mixture was administered to an unstated number of random bred CHl mice from days 7-17 of gestation. Fetal mortality and development were unaffected at the 200 mg/kg dosage level. An unstated dose of pentachloroaniline was administered orally to random bred CB rats from days 7-18 of gestation. Animals were killed on the nineteenth day. Maternal weight was depressed but all other indices were normal (Courtney, 1973). Acute toxicity No further data. Short-term studies No further data. Long-term studies No data are yet available. Comments Further studies have confirmed that quintozene is absorbed from the gastrointestinal tract and rapidly excreted, the main metabolites being pentachloroaniline and methyl pentachlorophenol sulfide. The latter was found at higher concentrations than other metabolites in the fetuses of mothers exposed to quintozene. Studies have shown that pentachloroaniline has no teratogenic activity. An increased number of eye abnormalities, cleft palates and renal agenesis was reported in one mouse strain and cleft palates in another strain in teratogenicity studies in which 300 mg/kg doses of quintozene were administered, Lower dosage levels produced no abnormalities in mice and no teratogenic abnormalities were found in studies on rats. The reason for this difference has not been established. No studies have been carried out to explain the effects reported to occur in dogs and no other studies on pentachloroaniline have been made available. It was noted that long-term feeding studies in rats and mice are in progress and that results may soon be available. The Meeting considered that a temporary acceptable daily intake could be set for a further two years. TOXICOLOGICAL EVALUATION Level causing no significant toxicological effect Rat: 25 ppm in diet equivalent to 1.25 mg/kg bw Estimate of temporary acceptable daily intake for man 0-0.001 mg/kg bw RESIDUES IN FOOD AND THEIR EVALUATION Purity of quintozene Detailed gas-chromatographic analyses of technical quintozene, including its chemically related impurities, have been established (Olin Mathieson Co., 1973). The ranges covered by 10 samples from five different manufacturers are given as follows: Quintozene (PCNE) : 88.4-98.6 Tetrachloronitrobenzene (TCNB) : 0.3-3.9 Hexachlorobenzene (HCB) : n.d.-10.8 Pentachlorobenzene (PCB) : n.d.-1.2 Others, high boilers : n.d.-0.6 The high boiling fraction is identified, from one producer, as mainly consisting of tetrachlorodinitrobenzene, whereas attempts to detect any tetra- or octa-chlorodibenzo-p-dioxin have proved negative, within a detection limit of 0.05 ppm (Griffith and Thomas, 1972). From many additional samples analysed (CXPR, 1973) it is indicated that production procedures which favour a minimum content of MB, may give rise to increased amounts of pentachlorobenzene. Thus, three samples containing less than 0.1% HCE, contained up to 3.6% pentachlorobenzene. Use pattern While no significantly different use patterns have been described, some additional information on already established uses has been received. Residues resulting from supervised trials Kuchar et al. (1973) have supplied further data on residues found after field trials, setting out the analytical findings individually for quintozenep pentachlorobenzene and hexachlorobenzene (HCB), as well as for the metabolites pentachloroaniline (PCA) and methyl pentachlorophenyl sulfide (MPCPS). This information is summarized in Table 1 reporting the maximum residues only. The results indicate that total residues resulting from approved uses largely conform to the temporary residue limits recommended by the 1969 meeting, the exception being peanut kernels for which the composite residues following recommended use patterns suggest 2 ppm as a more realistic level. From information presented by the Netherland delegation to the sixth session of the Codex Committee on Pesticide Residues and later directly to the Joint Meeting, it has become evident that there exists an established and definite need for quintozene to control prevailing fungi complexes of Botrytis and Sclerotinia species which in some countries has justified a yearly preplanting soil treatment of 3 g a.i. per m2. Results from supervised trials (see Table 2) demonstrate that such registered use regularly gives residues in lettuce heads, which, however, only occasionally exceed 3 ppm. Results of analysis show that quintozene is not evenly distributed in the harvested crop. A three to four fold higher concentration is found in the outer leaves of individual heads than in the remaining inner parts. This leads to the conclusion that a major part of the residues results from vapour transfer from the soil under closed glasshouse conditions rather than by way of absorption through the roots. Fate of residues In plants The above residue data confirms a slight systemic uptake from soil into plants. Residues of impurities in the technical product (i.e. HCB and PCB) and the metabolites formed in soil and/or plants (i.e. PCA and MPCPS) usually comprise the greater part of total residues. A significant increase of PCB relative to HCB compared to the ratios in technical quintozene is noted simultaneously with the formation of PCA and MPCPS. TABLE 1. RESIDUES OF QUINTOZENE, METABOLITES AND IMPURITIES IN VARIOUS CROPS Crop Application Quintozone PCB HCB PCA NPCPS rate Beans, Lima 0.5-1.5 lb/ 0.029 n.d. n.d. 0.014 n.d. acre Beans, Snap 2 lb/acre n.d. n.d. n.d. n.d. n.d. Cabbage 15 lb/acre 0.004 n.d. 0.001 n.d. 0.015 Peanuts 10 lb/acre 0.015-0.269 0.002-0.148 0.012-0.278 0.028-0.324 n.d.-0.42 Peanut hulls 10 lb/acre 0.51-0.98 0.04-0.109 0.03-0.310 0.34-0.90 0.03-0.27 Peas 1.5 lb/acre 0.007 n.d. n.d. n.d. n.d. Potatoes 25 lb/acre 0.004 0.044 0.008 0.025 0.013 Potatoes, 25 lb/acre 0.002 0.040 0.007 0.020 0.008 peeled Potatoes, 25 lb/acre 0.026 0.080 0.018 0.066 0.057 peel only Potatoes 50 lb/acre 0.024 0.059 0.014 0.031 0.033 TABLE 2. QUINTOZENE RESIDUES IN GLASSHOUSE LETTUCEa (Treatment: 3 g a.i./m2, before planting) 13 Weeks after planting: 9 10.5 12 (Harvest) Exp. 1 Weight of lettuce head (g) 5.4-5.7 13.8-15.2 36.2-39.6 75.8-92.6 Quintozen (ppm) 2.3-2.7 1.7-2.2 1.7-3.5 2.0-2.7 Exp. 2 Weight of lettuce head (g) 17.8-17.9 37.0-37.2 85.3-92.7 162.5-168.2 Quintozene (ppm) 2.2-2.7 2.5-3.2 1.0-2.9 1.2-2.2 a Each figure represents average of four replicates. Data corrected for non-treated controls. A definite uptake of quintozene and derivatives by both potatoes and carrots grown in treated soils is demonstrated in the first year of a two-year study by Beck and Hansen (1973b), the results of which is summarized in Table 3. A second-year residual uptake is further evident in carrots (a total of 0.59 ppm), but not detectable in potatoes. The sum of impurities and metabolites constituted up towards 507 of total residues in those studies with PCA and MPCPS as the major components. TABLE 3. TWO-YEAR STUDY OF QUINTOZENE UPTAKE IN CARROTS AND POTATOES (from Beck & Hansen, 1973b) Date of Residues in ppm Treatment Harvest Quintozene Tecnazene PCB HCB PCA MPCPS Carrots (60 kg a.i./ha per treatment) May 1970 September 1970 1.00 n.d. 0.02 0.03 n.d. n.d. May 1970 September 1971 0.45 0.02 0.09 0.03 0.06 0.04 May 1970 + May 1971 September 1971 2.02 0.06 0.07 0.07 0.11 0.07 Potatoes (60 kg a.i./ha per treatment) May 1970 October 1970 0.20 0.01 0.02 0.03 0.03 0.04 May 1970 September 1971 n.d. n.d. n.d. n.d. n.d. n.d. May 1970 + May 1971 September 1971 0.20 0.01 0.03 0.04 0.05 0.05 In animals Results of experimental feeding of residual quintozene to rats, dogs and cows have been published (Borzelleca, 1971). No quintozene could be found in tissues in these studies; neither could quintozene be identified in milk from cows receiving 0.1-10 ppm in rations. Pentachloroaniline and methyl pentachlorophenyl sulfide were found in tissues as metabolites of quintozene. The studies confirmed an apparent lack of metabolism of hexachlorobenzene and pentachlorobenzene which were stored in tissues in concentrations reflecting the level of these impurities in the technical quintozene. Results from the feeding of cows at the 1 ppm and 10 ppm level are summarized in Table 4. Only HCB (and PCD at the 10 ppm level) residues was noticeable in the milk. In soil The apparent high persistence of quintozene in soils has been confirmed by Beck and Hansen (1973a) through laboratory experiments, supplemented by a soil sampling programme from potato fields which had been treated intermittently through the proceeding 5 to 11 years. An average half-life of 14 months was calculated from 22 field samples. Quintozene losses from three California soils (fine sandy loam, and clay soil and peaty mulch) are described by Wang and Broadbent (1972) as following first-order reactions with halflives from 4.7-9.6 months. These authors further find evidence that volatilization is of major significance in accounting for the losses of the compound. The possibility of losses of quintozone to the atmosphere from soil under field conditions is also described by Caseley (1968). Degradation of quintozene in soils through microbial and/or chemical processes is further confirmed as important. Chako et al. (1966) found that eight soil fungi and eight actinomycetes, grown in nutrient media, degraded PCNB. Streptomyces aureofaciens reduced the largest quantity of PCNB, producing pentachloroaniline (PCA). Nakanishi and Oku (1969) and Kaufmann, (1970) also demonstrated in addition to PCA, methylthiopentachlorobenzene (MPCPS) as a microbially produced metabolite. In the laboratory experiments by Beck and Hansen (1973a) evidence was given that not only PCA and MPCPS, but also pentachlorobenzene (PCB) could be produced from quintozene in soils. From the above-mentioned soil sampling programme (Beck and Hansen (1973a)) average content of quintozene plus impurities and metabolites was found as shown in Table 5. The highest individual level was a total of 28.8 ppm found in a field which had been treated three times within five years with 30-60 kg a.i./ha, the last time one year before sampling. TABLE 4. RESIDUES IN COW TISSUES AND MILK AFTER FEEDING QUINTOZENEa AT THE RATE OF 1 ppm AND 10 ppm IN THE RATION For 12 weeks 8 weeks Fat (abdom.) Sk. Muse. Liver Kidney Milk PCNB 1 ppm n.d. n.d. n.d. n.d. n.d. 10 ppm n.d. n.d. 0.031 n.d. n.d. TABLE 4. (cont'd) For 12 weeks 8 weeks Fat (abdom.) Sk. Muse. Liver Kidney Milk PCA 1 ppm 0.005 n.d. n.d. n.d. n.d. 10 ppm 0.499 0.018 n.d. 0.043 0.006 MPCPS 1 ppm 0.017 n.d. n.d. n.d. n.d. 10 ppm n.d. n.d. n.d. 0.020 n.d. PCB 1 ppm n.d. n.d. n.d. n.d. n.d. 10 ppm 0.001 n.d. n.d. n.d. n.d. HCB 1 ppm 0.046 0.008 n.d. 0.001 0.003 10 ppm 0.618 0.015 n.d. 0.005 0.015 a Composition of technical Qintozene: PCNB: 97.8%, HCB: 1.8%, PCB: <0.1% and TCNB: 0.4% TABLE 5. RESIDUES OF QUINTOZENE AND RELATED COMPOUNDS IN SOIL PROM 22 PREVIOUSLY TREATED FIELDS Treated 1-5 times Treated 1-4 times until 3 years before until 1 or 2 years sampling before sampling Average (range) -ppm Average (range) - ppm Quintozene (PCNB) 5.44 ppm (0.01-12.8) 8,41 ppm (1.47-25.3) Tecnazene (TCNB) 0.09 ppm (n.d-0.18) 0.12 ppm (0.03-0.28) PCB 0.37 ppm (0.003-0.84) 0.32 ppm (0.16-0.77) HCB 0.35 ppm (n.d.-0.53) 0.41 ppm (0.17-0.94) PCA 2.11 ppm (0.01-4.10) 1.28 pp. (0.28-3.31) MPCPS 0.38 ppm (n.d.-1.07) 0.29 ppm (0.03-0.73) (From Beck and Hansen, 1973a) Residues in food commodities in commerce Quintozene analyses have been included in regular market sample programmes for pesticide residues in two Scandinavian countries (Voldum-Clausen, 1973; Westöö and Norén, 1973). In the one country during the years 1969 to 1972 quintozene was found in 48% of carrots, 49% of potatoes and 43% of lettuce in a total of 454 samples. In the other country 34%, 46% and 14% of the samples of lettuce, parsley and carrots were found positive respectively. These programmes comprised food items of both domestic and foreign origin. In the case of the domestic products, quintozene residues in potatoes, parsley and lettuce are the result of intentional applications, whereas residues in carrots are presumed to be unintentional, resulting from uptakes from previously treated soils (Beck and Hansen, 1973a and 1973b). Quintozene residues in lettuce were similarly reported by the Netherland delegation to the sixth session of the Codex Comittee on Pesticide Residues, 1972. Surveys in that country had indicated that the frequency of positive samples was significantly higher during the season of glasshouse growing (61% positive from January to April) than during summer months (32.5% positive from May to June) (CCPR, 1972). Residue levels in these three surveys were generally below 3 ppm with the exception of only a few individual lettuce samples. Methods of residue analysis Gas-chromatographic methods which allow the determination of quintozene and its individual impurities and metabolites have been described by several authors (Kilgore and White, 1970; Collins et al., 1972; Beck and Hansen, 1973 and Kuchar et al., 1969). The method described by the latter authors determine PCNB, PCB, HCB and PCA in animal tissues, blood, bile and urine with a determination limit of 0.005 ppm for each of the compounds and with average recoveries ranging from 84 to 1077. For MPCPS it was established that recoveries of 87-105% were obtained at the 0.1 ppm level. Their method uses extraction with acetonitrile and partitioning into hexane followed by GLC with electron capture detector. Baker and Flaherty (1972) have adapted an earlier multiresidue method for chlorinated pesticides (de Faubert Maunder et al. (1964)) for the determination of quintozene in tomatoes, lettuces and bananas, as representative products on which quintozene may be used. It consists of extraction with hexane, partitioning with dimethylformamide and column chromatographic clean-up on alumina. Quantitative determination using electron capture gas-chromatography may be supplemented by a confirmatory chemical test for quintozene based on reduction to PCA, which is then determined by GLC. This method shows recoveries of 83-94% at the 0.005-0.1 ppm level in tomatoes, 75-103% for 0.01-5.0 ppm in bananas and 90-108% for 0.01-5.0 ppm in lettuce. National tolerances Some national tolerances reported in 1969 (FAO/WHO, 1970) have been changed and new tolerances have been established. The following is a list of national tolerances available to the Meeting. Federal Republic Lettuce 0.3 ppm of Germany Oil Seeds 0.03 ppm Cabbage 0.02 ppm Bananas, without peel) Other vegetable foods) 0.01 ppm Netherlands and Fruits and vegetables, Belgium except potatoes 1.0 ppm Leafy Vegetables 3.0 ppm United States of Cotton-seed 0.1 ppm as negl. America residue Others Originally on "no residue basic". At present under review German Democratic Potatoes 5.0 ppm Republic Potatoes, peeled 0.5 ppm Cabbage 0.3 ppm Switzerland Lettuce, wheat 1.0 ppm Cereal products, 0.1 ppm flour, bakery products, etc. Appraisal Since the evaluation of quintozene in 1969 further information has become available on several of the questions which were raised. More detailed information has been received on technical quintozene and its impurities. Depending on the production procedure varying amounts of impurities may be formed. Dominant are hexachlorobenzene (levels ranging from (< 0.1 to 10.8%), pentachlorobenzene (from (< 0.1 to 3.6%) and tetrachloronitrobenzenes (from 0.3 to 3.8%). Additional data on quintozene residues (including metabolites and impurities) derived from supervised trials indicate that residue levels largely conform to the temporary tolerance levels recommended by the 1969 Joint Meeting, the exception being peanut kernels on which the composite residues of parent compound, metabolites and impurities following recommended use patterns are such as to require a limit of 2 ppm. Results of studies carried out on the use of quintozene for the control of fungal complexes of Botrytis and Selerotinia in lettuce grown in glasshouses were evaluated. A yearly proplanting soil treatment of 3 g a.i./m2 as registered in some countries was found in extensive supervised trials to give rise to residues which only occasionally exceed 3 ppm. This established use pattern is reflected in published data on residues found in lettuce moving in commerce indicating that up to 43% of samples of commercial lettuce may carry quintozene residues, the frequency being considerably higher in the winter season than during summer when lettuce is mainly grown in the open air. Market sample surveys in European countries further show that residues of quintozene (including impurities and metabolites) may be present in up to 50% of root vegetables (carrots and potatoes) examined. The residues in potatoes result from deliberate soil applications during the growth of the crop whereas residues in carrots originate from growing the crop in soils previously treated for another crop. Further studies of the persistence of quintozene in soils were presented to the Meeting. Half-life values of from 4.7 to 9.6 months were found in three Californian soils, whereas an average of 14 months was required to give 50% degradation under more temperate Scandinavian conditions. Results of experiments where quintozene was fed to rats, dogs and cows have been published. These studies confirmed an apparent lack of metabolism of hexachlorobenzene and pentachlorobenzene which were stored in tissues in concentrations reflecting the level of these impurities in the technical quintozene. Excretion with the milk was noticeable in the case of HCB. Analytical methods for the determination of quintozene and individual impurities and metabolites based on GLC-technique and suitable for regulatory purposes are now available. RECOMMENDATIONS FOR TOLERANCES, TEMPORARY TOLERANCES OR PRACTICAL RESIDUE LIMITS Recognizing that the major problem resulting from the use of quintozene is the presence of persistent and intractable residues of impurities, especially hexachlorobenzene, in the technical product it is recommended that every effort should be made to encourage manufacturers to reduce the amount of these impurities to the minimum. The temporary tolerances recommended in 1969 have been confirmed. New data justifies revision of the tolerances for lettuce and peanuts and the following recommendations are made. Tolerance Lettuce 3 ppm Peanuts (kernels) 2 ppm It should be noted that the limits for quintozene residues in all commodities include not only quintozene but the following impurities and metabolites: hexachlorobenzene; pentachloroaniline; methyl pentachlorophenylsulfide pentachlorobenzene. FURTHER WORK OR INFORMATION Required before 1975 1. Carcinogenicity studies in two species of animal. 2. Short-term studies to elucidate the difference in the teratogenic activity in rats and mice. 3. Studies to explain the effects on the liver and bone marrow of dogs. 4. Comparison in rats and mice of the absorption, distribution, and excretion of quintozene, its metabolites and any contaminants present in significant concentrations in the technical product. 5. Further studies on the toxicity of metabolites. 6. Studies to show the nature and levels of residues in meat, milk, and eggs following the feeding of quintozene residues in animal feeds. REFERENCES Baker, P.B. and Flaherty, B. (1972) Fungicide residues. Part I. The detection, identification and determination of residues of quintozene in tomatoes, lettuces and bananas by gas chromatography. 97: 378 Beck, J. and Hansen, K.E. (1973a) The degradation of quintozene, pentachlorobenzene, hexachlorobenzene and pentachloroaniline in soil. Paper submitted for publication in Pesticide Science Beck, J. and Hansen, K.E. (1973b) Uptake in carrots and potatoes of quintozene, related impurities and metabolites from soil. Information from National Food Institute and Government Plant Pathology Institute, Copenhagen (Unpublished) Borzelleca, J.F., Larson, P.B., Crawford, E.M. Honnigar, G.R., Kuchar, E.J. and Klein, H.H. (1971) Toxicol. and Appl. Pharm. 18. 522-534 Caseley, J.C. (1968) The loss of three chloronitrobenzene fungicides from the soil. Bulletin Envir. Contam. & Toxicol. 3: 180 CCPR. (1972) Comments from the Netherland delegation to the 6th meeting of Codex Committee on Pesticide Residues. Document no. 9023 CCPR. (1973) Reply from Netherland delegation to question B(11), Residues of quintozene in lettuce and potatoes (par. 124, ALINORM 72/24A, ref. CL 1972/30, Febr. 1973) Chako, C.I, Lockwood, J.L. and Zabik, M. (1966) Chlorinated hydrocarbon pesticides: degradation by microbes. Science, 154; 893 Collins, G.B., Holmes, D.C. and Wallon, M. (1972) Identification of hexachlorobenzene residues by gas-liquid chromatography. J. chromatography, 69: 198 Courtney, D. (1973) Paper presented to Society of Toxicology, New York Crosby, D.G. and Hamadmad, N. (1971) The photoreduction of pentachlorobenzenes. J. Agr. Food Chem. 19: 1171 FAO/WHO. (1970) 1969 evaluations of some pesticide residues in 1970 food FAO/PL: 1969/M/17/1. WHO/FOOD ADE./70.38 de Faubert Maunder, M.J., Egan, H., Godley, E.W., Hammond, E.V., Roburn, J. and Thomson, J. (1964) Clean-up of animal fats and dairy products for the analysis of chlorinated pesticide residues. Analyst, 89: 168 Griffith, W. P. and Thomas, R.J. (1972) 1,2,3,4,6,7,8,9-octachloro- dibenzo-p-dioxin in pentachloronitrobenzene. Report CASR-3-72 of February 28, 1972 from Chemicals Division, Central Analytical Department, Olin Corporation (Unpublished) Jordan, R.L. and Borzelleca, J.P. (1973) Teratogenic studies with pentachloronitrobenzene in rats. Paper presented to the Society of Toxicology, New York Kaufman, D.D. (1970) Pesticide Metabolism, pages 73-85. In: pesticides in the soil: Ecology, degradation and movement. International symposium on pesticides in the soil. Feb. 1970. Michigan State University. East Lansing Kilgore, W.W. and White, E.R. (1970) Gas chromatographic separations of mixed chlorinated fungicides. Journ. Chromatographic Science, 8: 166 Kuchar, E.J., Geenty, F.O., Griffith, W.P. and Thomas, R.J. (1969) Analytical studies of metabolism of terraclor in beagle dogs, rats, and plants. J. Agric. Food Chem. 17: 1237 Kuchar, E.J., Griffith, W.P. and others. (1973) Residues of terraclor, impurities and metabolites in various crops (1969-72). Report CASR-2-73 of January 8 1973 submitted by the Olin Corporation (Unpublished) Nakanishi, T. and Oku, H. (1969) Metabolism and accumulation of pentachloronitrobenzene by phytopathogenic fungi in relation to selective toxicity. Phytopathology 59: 1761 Olin Mathieson Corporation. (1973) Various analytical investigations concerning terraclor and quintozene from various sources. Tabulated information submitted by the Olin Corporation (Unpublished) Searle, C.E. (1966) Tumour initiatory activity of some chloromononitrobenzene and other compounds. Cancer Research 26: 12-17 St. John, L.E., Ammering, J.W., Wagner, D.G., Warner, R.G. and Lisk, D.J. (1965) Fate of 4,6-Dinitro-2-isobutylphenol, 2-chloro-4,6-Bis- (Ethylamino)-S-Triazine and Pentachloronitrobenzene in the Dairy Cow. J. Dairy Sci. 48: 502-503 Voldum-Clausen, K. (1973) Pesticide residues in Danish food, 1969- 1972. Publication no. 20, July 1973 from National Food Institute, Soborg, Denmark Wang, C.H. and Broadbent, F.E. (1972) Kinetics of losses of PCNB and DCNA in three California soils. Soil Set. Soc. Amer. Proc. 36: 742 Westöö, G. and Norén, K. (1973) Residues of organochlorine pesticides and certain organophosphorus pesticides in fruits, berries, vegetables, and roots, 1968 June 1972. Vår Foda 25: Suppl. 1, 6 (Stockholm)
See Also: Toxicological Abbreviations Quintozene (EHC 41, 1984) Quintozene (HSG 23, 1989) Quintozene (ICSC) Quintozene (FAO/PL:1969/M/17/1) Quintozene (WHO Pesticide Residues Series 4) Quintozene (WHO Pesticide Residues Series 5) Quintozene (Pesticide residues in food: 1977 evaluations) Quintozene (Pesticide residues in food: 1995 evaluations Part II Toxicological & Environmental)