CARBENDAZIM JMPR 1973 IDENTITY Chemical names Methyl-2-benzimidazole carbamate Methyl benzimidazole-2-ylcarbamate 2-(methoxy-carbamoyl)-benzimidazole 2-(methoxycarbonylamino)benzimidazole Carbomethoxyaminobenzimidazole Synonyms Bavisitin(R), MBC, MCAB, BCM, Hoe 17411, Drosal Structural formulaOther information on identity and properties Molecular weight: 191.2 State: light grey powder Melting point: 307-312°C (decomposition) Vapour pressure: 0.1 × 10-6 mmHg (20°C) Solubility: Soluble in acetic acid and dimethyl-formamide Water, pH 4: 28 ppm Water, pH 7: 8 ppm Water, pH 8: 7 ppm Hexane: 0.5 ppm Benzene: 36 ppm Methylenechloride: 68 ppm Ethanol: 300 ppm Acetone: 300 ppm Chloroform: 100 ppm Stability: Stable in acidic and alkaline solutions at room temperature and when exposed to light. Stable in storage at 35-50°C Purity of technical product: Better than 98% EVALUATION FOR ACCEPTABLE DAILY INTAKE Biochemical aspects Methyl-2-benzimidazole carbamate has been proposed as an intermediate in the degradation of thiophanate and benomyl in plants. The quantitative aspects of this conversion have not been fully reported although it appears that, while carbendazim is a major metabolite, there may only be limited conversion of the two parent molecules (Douch, 1973). Sims et al. (1969) found only carbendazim but not benomyl four weeks after treatment of cotton. In aqueous solution benomyl and thiophanate methyl were reported to convert rapidly to carbendazim (Clemons and Sisler, 1969; Buchenauer and Edgington, 1973). In pea plant treated with benomyl, only carbendazim was recovered as a plant residue (Siegel and Zabbia, 1972). In aqueous solution on glass following irradiation by ultra-violet or sunlight, conversion of both thiophanate and thiophanate methyl to ethyl-2-benzimidazole carbamate and carbendazim was effected. There are no data available on the metabolism of carbendazim in either mammals or plants. Metabolism of benomyl in mammals also results in the occurrence of 5-hydroxy carbendazim and other products (Douch, 1973; Gardiner et al., 1968). This might arise directly from benomyl by oxidation and hydrolysis or by hydrolysis of benomyl to carbendazim followed by oxidation. Carbendazim is the major metabolite of benomyl in plants. A minor metabolite from benomyl is believed to be 2-amino benzimidazole. The probable metabolic pathway of carbendazim based upon data derived from thiophanate and benomyl conversion is suggested as follows:
Clemons and Sisler (1971) have suggested that carbendazim appears to interfere with DNA synthesis or some closely related process such as nuclear or cell division in fungi. RNA and protein synthesis were not affected. Hammerschlag (1973) indicated an effect of carbendazim on mitosis, DNA synthesis and cytokinesis in two fungi species. Certain differences in effects of benomyl and carbendazim were attributed to the occurrence of butylisocyanate, a potential metabolite of benomyl. TOXICOLOGICAL STUDIES Special studies on mutagenicity Mouse. Groups of mice (20 male mice per group) were used in a dominant lethal study where one group was administered a dose of 1280 mg/kg carbendazim by i.p. injection and three other groups served as controls (Hofmann and Peh, 1973). One group was a solvent control, one an unhandled control and one a positive control. Each male mouse was mated with three females for seven days over a period of eight weeks. The females were sacrificed at day 18 following introduction to the males and various reproduction parameters examined, including implantation, total number of live and dead fetuses, and resorption sites. There were no apparent effects as a result of MBC administration to males except a slight growth depression during week 1. During the same week, the mutagenic index was higher in the treated group than in the untreated controls, although not different from that in the solvent controls. The effect was considered to be within the normal variation. A positive control (Trenimon, 2,3,5-triethyleneimino benzoquinone-1,4) showed definitive effects especially during the first three weeks of the experiment. Methyl-benzimidazole carbamate does not appear to be mutagenic to mice as evidenced by this dominant lethal study (Hofmann and Pen, 1973). Acute toxicity Dermal injection of 0.01% (2 µg) to rabbits caused slight reddening around the injection site (Scholz and Weigand, 1972). There were no effects noted following five daily dermal applications of 500 mg to unbroken skin of rabbits. Application of 10 mg to the conjunctival sac of rabbits caused a transient reddening. No such effects were noted with 5 mg. Species Sex Route LD50 Reference (mg/kg) Rat M & F oral > 15 000 Hofmann, 1971, 1972c; Scholz and Weigand, 1973a M oral > 15 000 Scholz and Weigand, 1972b Species Sex Route LD50 Reference (mg/kg) F oral 14 000 Scholz and Weigand, 1972b M i.p. 7 230 Scholz and Weigand, 1972a F i.p. 715 000 Scholz and Weigand, 1972a Mouse M & F i.p. > 5 000 Scholz and Weigand, 1972a; Hofmann and Peh, 1973 Dog M & F oral > 8 000 Zeller and Kirsch, 1971a; Scholz and Weigand, 1972a Rabbit M & F oral > 8 000 Zeller and Kirsch, 1971b Japanese M oral 10 996 Scholz and Weigand, 1973b quail (sesamol) 15 595 Scholz and Weigand, 1973b (starke-schleim) F 5 826 Scholz and Weigand, 1973b (sesamol) 9 813 Scholz and Weigand, 1973b (starke-schleim) Short-term studies Rat. Groups of rats (10 males per group) were administered carbendazim orally for two weeks (by gavage) at dosage levels of 0, 10, 20, 30 and 40 mg/kg per day. The object of the study was to assess toxicity with special reference to the effect on bone marrow and the male reproduction system. One hour before sacrifice, each animal was injected with tritiated thymidine. At the conclusion of the study, the following tissues were removed, organ weights were recorded and organ to body weight ratios were calculated: adrenal glands, brain, heart, kidney, liver, pituitary gland, spleen, testes and thyroid gland. Microscopic examination was perfumed on the bone marrow and testes of all rats from the control and high-dose group. Microscopic radio-autography was used to determine bone marrow mitosis. Bone marrow was dissected, fixed and processed in paraffin wax. Sections were mounted on microscope slides and exposed to Kodak stripping film. After 20 days, the slides were developed, fixed and counted as well as examined following staining with haematoxylin. There were no effects noted in behaviour, mortality, food consumption and body weight gain. On gross examination of tissues, it was observed that the absolute and relative liver weight of rats at the 40 mg/kg dosage was higher than the controls. A decrease in relative testes weight, although significant, did not appear to be dose related and did not appear to be significant in this study, especially as there were no histological abnormalities observed in testes. Bone marrow examinations in both control and treated animals were within normal limits and showed no significant abnormalities either histologically or on radio-autography of the bone marrow cells. This study indicates that a dosage level of 30 mg/kg per day administered orally for two weeks would be a no-effect level with an effect noted at 40 mg/kg per day with regard to liver to body weight ratio (Hunter et al., 1973a). Groups of Sprague-Dawley strain rats (10 male and 10 female per group) were fed carbendazim in the diet at dosage levels of 0, 2000, 4000 and 8000 ppm for 28 days. Haematological examination, clinical chemistry and urinalyses were performed at three weeks of testing. Gross and microscopic examination of tissues and organs was Performed at the end of the feeding study. Food consumption and growth were depressed at 4000 and 8000 ppm. Urinalysis and blood chemistry were not affected by the treatment, while a tendency was noted at 8000 ppm of an increase in haemoglobin concentration and white and red blood cell counts. Gross Pathology appeared normal and at histopathological examination degeneration of testicular tissue was found at 4000 and 8000 ppm. Also spermatogenesis and oogenesis were affected at these feeding levels. Some changes were found in the weights of different organs relative to body or heart weight. of most significance was the increase in absolute and relative liver weight, which was also found in the lowest dosage group, 2000 ppm in the diet. No changes relative to the controls were found at histological examination of livers from the dosed groups (Hofmann and Kitsch, 1972). Groups of Sprague-Dawley albino rats (30 male and 30 female rats per group) were fed carbendazim at dose levels of 0, 50, 150, 450 and 1350 ppm in the diet for 13 weeks. At the conclusion of this study, 10 males and 10 females from each group were maintained on a control diet for a recovery period of six weeks. Food consumption and behavioural changes were examined daily and body weights weekly. Urine analysis, haematological and blood chemistry investigations were carried out periodically. Gross and microscopic examinations of tissues and organs were performed at the end of the study. Food intake in females receiving 1350 ppm was slightly depressed during recovery phase. Body weight gains in all groups at any dose level remained closely comparable to controls. Growth, urine analysis, blood chemistry and haematological findings were within the normal range except females receiving 1350 ppm who exhibited depression of total serum proteins. Relative liver weight in males and females was significantly increased at 1350 ppm. Absolute liver weight was elevated significantly at 1300 ppm in females. In rats allowed a recovery period of six weeks, no treatment-related differences in relative or absolute liver weight was observed. Gross and microscopic examinations of tissues and organs did not show any consistent finding at any dose level (Hunter et al., 1973b). Groups of rats (20 male and 20 female rats per group) were fed carbendazim at dose levels of 0, 80, 400, 2000 and 10 000 ppm in the diet for 93 days. Food consumption and behaviour were examined daily and body weight gain was measured weekly. Haematological examinations, blood chemistry and urinalyses were perfumed at 0, 45 and 92 days. At the conclusion of the study, half of the animals were sacrificed and the remaining animals were maintained on normal feed for two weeks after which they were sacrificed. Gross and microscopic examinations were made on tissues and organs. A minor reduction in growth occurred at 10 000 ppm and mortality was noted at this level. There was no effect on food consumption at any dose level. There were no effects on behaviour, and haematological and urinalyses values were normal. Blood chemistry was normal except that, at the conclusion of the study, there appeared to be a slight increase of uric acid in the blood at 10 000 ppm in both males and females. Gross examination of the tissues and organs of females sacrificed immediately at the conclusion of the feeding study indicated an increase in the absolute liver weight. The absolute liver weight of males was increased at the two highest dose levels only. There was a slight increase in liver to body weight ratio in females sacrificed 12 days after the feedings study ended. This was not reflected in males. The increase in absolute liver weight observed in females at 80 ppm which did not begin to occur until 2000 ppm in males appears to be the most sensitive parameter noted in the study. As this effect was not observed to influence the liver to body weight ratio, except at dietary concentrations of 400 ppm and above, the no-effect level in rats was 80 ppm. Gross pathology was not consistently different from the controls at any dose level. At histological examination no lesions were demonstrated to be a result of feeding carbendazim at levels including 10 000 ppm. No histological changes of the liver tissue were found (Scholz et al., 1973). Dog. Groups of dogs (three male and three female beagle dogs per group) were fed carbendazim in the diet at dose levels of 0, 500, 1500 and 4500 ppm for three months. Haematological examinations, blood chemistry and urinalyses were performed at 0, 6 and 12 weeks. There were no signs of poisoning observed in the study and animals showed no differences in behavioural response. A reduction in body weight was observed at 4500 ppm. Clinical chemistry and haematological values were normal. An increase in absolute and relative liver weight in males was noted at 4500 ppm and in females at 1500 ppm. The relative weight of adrenals was slightly increased in males at 1500 ppm. The heart weight was significantly reduced in females at 4500 ppm. Histological examination of the liver in the 4500 ppm dose group revealed perivenous infiltrates and zones of asymmetric proliferation in the periportal areas or in the liver parenchyma with liver cell regeneration and local hyperaemia. These changes together with signs of broncho pneumonia were considered to be of infectious origin and not related to the carbendazim treatment. No other tissues showed any adverse histological effects. A slight and not significant effect on the liver weight of female dogs of the level 500 ppm of carbendazim in the diet is considered marginal, but cannot be completely dismissed on the basis of examination of three animals (Kirsch et al., 1973). Long-term studies None available. Comments Carbendazim, methyl 2-benzimidazole carbamate, is a fungicide of low acute toxicity. Its fate in animals is not known and needs to be clarified. Limited studies on mice and rats have indicated no mutagenic potential or adverse effect on the male sex organs although high levels resulted in testicular damage. Data is not available on the effect of carbendazim on reproduction or on its teratogenic potential. In short-term studies in the rat and the dog an increase in the liver weight was the most significant Pinding. This effect was marginal at 80 ppm in the rat and at 500 ppm in the dog and was substantial at 400 ppm and at 1500 ppm in the rat and dog respectively. No histological changes were seen in the liver. Because of the observed effect on the liver and as no long-term or reproduction studies were available, an acceptable daily intake for man was not established. RESIDUES IN FOOD AND THEIR EVALUATION Use pattern Carbendazim, or MBC, was introduced as a commercial fungicide in 1972 and has through 1972-1973 obtained registration and approval for specified pre-harvest treatments in a number of countries in temperate, subtropical and tropical regions (see Table 1). It is available as wettable powder formulations or as dispersions containing 60 and 20% active ingredient, respectively. Carbendazim is generally recognized as the chemical entity, which is mainly responsible for the fungitoxic activity of some other systemic benzimidazole fungicides, including benomyl and thiophanate-methyl. From these, MBC is formed as the major metabolite in and on plant material. Accordingly, the antifungal effects of carbendazim are described as practically similar to the two mentioned chemicals, i.e. it is a broad-spectrum, systemic fungicide which is active against moulds, rots and blight. It is claimed effective against apple scab, powdery mildew, botrytis and Penicillim induced decay of citrus fruits. TABLE 1. INFORMATION ON REGISTERED AND APPROVED USES OF CARBENDAZIM (SEPTEMBER 1973) Countries in which Registered for following crops registered Australia stone fruit, strawberries, apples, pears, peanuts, cucumbers Austria apples, cucumbers, grapes, lettuce Colombia bananas, coffee, rice Costa Rica tropical crops, grapes, vegetables, ornamentals, hops El Salvador coffee, vegetables, cotton England apples, blackcurrants, beans, gooseberries, tomatoes, cucumbers, ornamentals, bulbs, grapes Ecuador bananas, rice France grapes, cereals, fruit Guatemala coffee, vegetables, cotton Holland bulbs Morocco bananas, pineapples New Zealand apples, citrus, roses, stone fruit Spain stone fruit, ornamentals, vegetables, pome fruit South Africa cotton, tobacco, vegetables Switzerland strawberries Uruguay vegetables, grapes, sugar beet, fruit Residues resulting from supervised trials Carbendazim residue data from pre-and post-harvest uses in different countries covering a range of single or repeated applications on fruits and vegetables has been presented by the manufacturers (Hoechst, 1973). A summarized list of residue ranges extracted from these data are presented in Table 2. Generally, most sprayings and dipping procedures tend to leave residues, the level of which is primarily governed by the applied dosages (concentration of active ingredient and number of treatments). The decrease in carbendazim residue levels with time seems consistent with a normal growth dilution effect following application, while chemical and/or physical losses seem to be of lesser importance, justifying the classification of carbendazim as a relatively persistent fungicide. Relatively stable deposits of carbendazim remain after the dipping of apples, citrus and bananas. In these fruits the residues are mostly concentrated on the peels. Citrus fruits, however, regularly show MBC residues penetrating into the edible inner parts of fruit in concentration ranges up to about one tenth of the corresponding peel concentrations. Fate of residues Plant material Gorbach et al. (1973) showed that MBC after foliar application to cucumber plants under greenhouse conditions mostly remained on the leaf surfaces. Only about 10% penetrated into the plant tissue. A translocation to other parts of the plant thereafter was hardly detectable (about 0.1% of the applied amount), but the dominant route of transportation was with the transpiration stream, i.e. towards the leaf edges. Solel and Edgington (1973) and others showed that plant penetration after foliar applications and movement through the cuticle is less for MBC than for bonomyl. They found, however, a definite translocation (1.11-1.68% of the applied amount) of MBC to roots, stems and shoots, when the application rates were 5-10 times higher than those used in normal practice (Solel et al., 1973). They suggest that a downstream movement in treated plants is insignificant at lower concentrations. MBC is more readily absorbed into plants through the roots (Gorbach et al., 1973). Seven days after adding 14C-carbendazim to a hydroponic-culture of cucumber plants up to 16 ppm was found in the plant material. Of these, 95% were present as MBC. The remaining 5% of radio-active material behaved like a single substance on TLC, concluded to be 2-aminobenzimidazole (2-AB). TABLE 2. RESIDUES OF CARBENDAZIM IN VARIOUS CROPS FROM PRE- AND POST-HARVEST TREATMENTS Application MBC-residues (ppm) Crop Country Rate Frequency Range (number) Apples 50-60 g/100 l Dipping 1.1-2.4 (27) Germany 100-500 g/ha 4-11 × 0.3-1.9 (53) Germany 600-900 g/ha 7-11 × 0.2-2.1 (27) Germany 1200-2400 g/ha 9-15 × 1.6-8.4 (36) Germany 490 g/ha 3 2.2-3.6 (12) Netherlands 825 /h. 3 2.1-4.9 (12) Netherlands Bananas 5-20 g/100 l Dipping Int.: n.d.-0.2 (8) Ivory Coast Peel: 0.5-2.0 (8) Ivory Coast 15-50 g/100 1 Storage Int.: n.d.-0.2 (35) Costa Rica Spray Peel: 0.1-0.9 (35) Costa Rica Barley 300-500 g/100 kg Seed n.d.-n.d. (10) Germany treatment Celery 450-1200 g/ha 7 × n.d-2.0 (12) England Cherries 3-4 g/tree 2 × n.d.-0.14 (6) Germany Coffee 660-1380 g/h. 1-7 n.d.-n.d. (5) Kenya (raw beans) Cucumber 250-500 g/ha. 2 × n.d.-0.35 (28) Gernany Gherkins 1000 g/ha 1 × 0.3-1.5 (8) Netherlands (under glass) Dwarf beans 450-1200 g/ha. 1 n.d-0.1 (6) England Gooseberries 720-900 g/ha. 4 1.6-2.2 (5) England Grapes 100-1120 g/ha. 4-10 0.3-9.3 (57) Germany Lemon 250 g/1100 l Dipping Int: 0.1-0.2 (13) Israel TABLE 2. (Cont'd.) Application MBC-residues (ppm) Crop Country Rate Frequency Range (number) Peel: 4.3-12.7 (13) Israel Mandarins 25-75 g/100 l Dipping Int: 0.2-1.2 (16) Spain Peel: 2.1-10.5 (16) Spain Oranges 23-75 g/100 l Dipping Int: n.d-1.4 (27) Spain Peel. 0.2-3.7 (27) Spain 250 g/100 l Dipping Int.: 0.1-0.7 (24) Israel Peel: 4.0-16.0 (24) Israel 600 g/ha 1 × Int: n.d. (2) South Africa Peel: n.d. (2) South Africa Peaches 400 g/h. 4 0.2-1.1 (12) Germany Strawberries 375 g/ha. 4-7 × n.d.-18a (32) Netherlands 600-2160 g/h. 2-3 × n.d.-1.2b (30) Germany Sugar beets 90-180 g/ha 2-3 Leaves: 0.1-4.8 (12) Germany Beets: n.d. (12) Germany Tomatoes 0.026-0.053 g/plant 4-8 × 0.5-1.4c (22) Netherlands 600-660 g/ha Winter wheat 125-480 g/ha 1 × Straw (0-14 days): 3.4 (16) Germany Straw (21-136 days): <0.1 (16) Germany Grains: n.d. (4) Germary Melons 0.01 g/plant 3 × Int.: n.d. Netherlands Peel: 0.6-0.8 (3) Netherlands Mushroom 6 kg/ha 1 × 0.5 (1) Netherlands a Sampled at 0-14 days after last application. b Sampled at 9-39 days after last application. c Surface residues only. Interior: not detectable. n.d. - not detected = < 40.05 ppm. Carbendazim treatment of sugar beets by spraying gives significant deposits of MBC on the leaves, but uptake of active material by the beet roots is not detectable (Anon., 1973). Animal tissues Studies of the metabolic degradation of MBC after direct feeding to animals has not been Presented, but by analogy to the available evidence on metabolism of benomyl it is anticipated that hydroxylation may take place to produce 5-hydroxymethyl-2-benzimidazolecarbamate, followed by urinary excretion as glucuronide or sulfate conjugates (Gorbach, 1973). Soil Carbendazim is a relatively stable compound and it is known to show some persistence in soil (Gorbach, 1973). Only data on low dosage treatments (90-180 g/ha) of sugar beets in the soil are presently available and these indicate no detectable residues (i.e. <0.01 ppm). Methods of residue analysis So far the most reliable analytical methods for the determination of benomyl are based on the conversion to MBC and eventual saponification to 2-aminobenzimidazole (Pease and Gardiner, 1969; Pease and Holt, 1971). These methods can easily be adapted for the determination of MBC. Details of U.V.-spectrophotometric methods used by the manufacturers of MBC have been presented (BASF, 1972; Gorbach, 1972). MBC is extracted from the slightly alkaline sample material with ethyl acetate. The ethyl acetate solution is extracted into 1 N sulfuric or hydrochloric acid and again transferred into ethyl acetate after pH adjustment. This procedure is repeated and MBC is finally partitioned into 1 N acid solution for spectrophotometric measurement at 281 nm. The detection limit of the method is given as 0.05 ppm and recoveries are 70-80% for various crops containing 0.1-0.5 ppm MBC. National tolerances According to the information available to the meeting, the following tolerances for carbendazim have been established: Australia Apples and pears 2 ppm Cucumbers 0.5 ppm Peanut kernels 0.1 ppm Federal Republic Citrus fruit 10 ppm of Germany Grapes 3.0 ppm (MBC residues Berries 2.0 ppm calculated as Vegetables (except cucumbers), benomyl) bananas, citrus fruits (without peel), stone fruit 1.0 ppm Cucumbers, cereals 0.5 ppm Bananas (without peel) 0.2 ppm Other plant produce 0.1 ppm Netherlands Fruit and vegetables 2 ppm Raw cereals (provisional) 0.5 ppm Appraisal Carbendazim is recognized as one of the major fungitoxic principles of the systemic benzimidazole fungicides, benmyi and thiophanate-methyl. Marketed as a fungicide on its own merits, it has obtained official registration in various countries and it is claimed to be effective in combating several fungal diseases, including apple scab, mildew and botrytis, and is applied both pre-harvest and post-harvest. A fair amount of data on residue in crops following approved foliar applications and dipping procedures has been made available to the Joint Meeting. Data were derived from supervised trials. Some studies involved excessive rates resulting in residue levels higher than would be likely following good agricultural practice. The residue levels reported generally reflect the dosages applied and the decline of residue levels mostly follows the pattern which characterizes growth dilution. Carbendazim is a chemically stable and relatively persistent fungicide which only metabolizes to a limited extent in plants and in soil. The only detected metabolite is 2-aminobenzimidazole, which constitutes less than 5% of the total residues in leaves. Although direct experimental data is lacking, carbendazim is expected to show relatively high persistence in soils. It is readily absorbed through the root systems of plants and, accordingly, there may be a possibility of unintentional uptake into subsequent crops. Data, on the other hand, that indicates that carbendazim may not reach through the soils into groundwater has been made available to the meeting. By analogy to other benzimidazole compounds, carbendazim may be anticipated to metabolize in the animal into hydroxylated analogues which may appear in meat and milk products. Analytical methods which may be adapted for regulatory purposes are available. RECOMMENDATIONS As no ADI could be established, no tolerances are recommended. Following officially acceptable use in various countries, residues of carbendazim can occur in the following commodities up to the levels indicated. The guideline levels indicated below are not likely to be exceeded when following good agricultural practice, including pre-harvest and postharvest treatments where applicable. For the underlined commodities, individual adjustments of recommendations have been made in order to accommodate good agricultural practices for such alternative systemic fungicides of which MBC is recognized and identified as the major metabolic and/or chemical entity (i.e. benomyl and thiophanatemethyl). Guideline levels ppm Citrus fruit (whole), peaches, cherries, grapes 10 Apples, pears, strawberries, tomatoes, lettuce, gooseberries 5 Gherkins, beans (dwarf), celery, plums 2 Mushrooms, bananas (whole) 1 Cucumbers, melons, bananas (pulp) 0.5 Raw cereals, sugar beet, coffee beans (raw) 0.11 Sugar beet tops 5 FURTHER WORK OR INFORMATION Required (before an acceptable daily intake can be estimated) 1. Long-term studies to investigate chronic toxicity and carcinogenicity. 2. Reproduction and teratogenicity studies. 3. Metabolism and distribution studies in several animal species. 4. Elucidation of the effect on the liver in female rats and dogs. 5. Information on the nature and level of residues in meat, milk, and eggs, after feeding animals on crops or feedstuffs treated with carbendazim. 1 At or about the limit of determination Desirable 1. Further studies to define the apparent "high-level" effects on male reproductive organs. 2. Information on the possible uptake from soils into subsequent crops. 3. Information on residues in food in commerce. REFERENCES Anonymous (1973) Evaluation of carbomethoxyaminobenzimidazole for the 1973 meeting of the Working Party of Experts on Pesticide Residues, 21 November - 5 December 1973, Geneva. Documents submitted by Farbewerke Hoechst AG and BASF Aktiengesellschaft (Unpublished) BASF Aktiengesellschaft (1972) Landwirtschaftliche Versuchsstation 1972 Limbürgerhof. Spektralphotometrische Bestimmung von BCM. Dated August 1972 (Unpublished) Buchenauerp H, Edgington, L.V. and Grossmann, F. (1973) Photochemical transformation of thiophanate-methyl and thiophanate to alkyl benzimidazole-2-yl carbamates. Pest. Sci. 4: 343-348 Clemons, G.P. and Sisler, H.D. (1969) Formation of a fungitoxic derivative from Benlate. Phytopath. 59: 705 Clemons, G.P. and Sisler, H.D. (1971) Localization of the site of action of a fungitoxic benomyl derivative. Pest Biochem. and Physiol. 1: 32-43 Douch, P.G.C. (1973) The metabolism of benomyl fungicide in mammals. Xenobiotica, 3(6): 367-380 Gardiner, J.A, Brantley, R.K. and Sherman, H. (1968) Isolation and identification of a metabolite of methyl 1-(butylcarboyl)-2-benzimidazole carbamate in rat urine. J. Agr. Food Chem. 16: 1050-1052 Gorbach, S. (1972) Analysenmethode zur Beatimmung von 2-Carbomethoxy aminobenzimidazole in Pflanzlichen Material. Paper presented by Farbewerke Hoechst AG (Unpublished) Gorbach, S. (1973) Ubersicht das Abbauverhaltens von Carbendazim (BCM) in Tier und Pflanze (Stand August 1973). Summary report presented by Farbowerke Hoechst AG (Unpublished) Gorbach, S, Thier, W. and SchuIze, E,F. (1973) Untersuchungen zum Rüchstandsverhalten und Metabolismus von Hoe 17411 OF-2-14C an Gurkenpflanzen unter Gewächshaus bedingungen. Forschungsbericht No. 221/73 submitted by Farbewerke Hoechst AG (Unpublished) Hammerschlag, R.S. (1973) Benomyl and methyl-2-benzimidazole carbamate (MBO: Biochemical, cytological and chemical aspects of toxicity to Ustilago maydis and Saccharomyces cerevesiae. Diss. Abstracts Int. 33(11): 5092B (Reviewed in Abstract in Health Aspect of Pesticides No. 73-2456) Hofmann, H. Th. (1971) Acute oral toxicity of methyl-2-benzimidazole carbamate to the rat. Unpublished report submitted by BASF AG Hofmann, H. (1972) Bericht uber die Prufung der akuten oralen oxizitdt von 2-(methoxy-carbamoyl)-benzimidazole an der Ratte. Unpublished report submitted by BASF AG Hofmann, H. Th. and Kirsch, P. (1972) Bericht uber die Prufung von 2-(methoxy-carbamoyl)-benzimidazole im 28-tage-futterungsversuch an der Ratte. Unpublished report submitted by BASF AG Hofmann, H. Th. and Peh, J. (1973) Bericht uber die Prufung von MCB (2-(methoxy-carbamoyl)-benzimidazole) auf mutagene Wirkung nach intraperitonealer applikation an der mannlichen Mans. Unpublished report submitted by BASF AG Hunter, B., Batham, F. and Newman, A.J. (1973a) BCM oral toxicity to rats. Daily administration for 2 weeks. Unpublished report from Huntingdon Research Centre submitted by BASF AG Hunter, B. Benson, H.G., Street, A.E., Heywood, R. and Newman, A.J. (1973b) BCM toxicity to rats during dietary administration for 13 weeks followed by a recovery period of 6 weeks. Unpublished report by Huntingdon Research Centre submitted by BASF AG Kirsch, P., Koob, K. Freisberg, K.O. and Birnsteil, H. (1973) Bericht über die Prufung der subchronischen - Toxizität von 2-(methoxy-carbamoyl)-benzimidazole (MCB) fur beagle-Hune bei oraler verabreichung. Unpublished report submitted by BASF AG Pease, H.L. and Gardiner, J. A. (1969) Fluorimetric and colorimetric procedures for determining residues of benomyl. J. Agr. Food Chem. 17, 267 Pease, H.L. and Holt, R.F. (1971) Improved method for determining benomyl residues. J. Assoc. Off. Agric. Chem. 54: 1399 Scholz, Schultes, D. and Bahr, Bericht (1973) über einen subchromischen Futterungs-versuch (93 tags) von HOE 17411 OF Techn. Wirkstoff. Unpublished report submitted by Farbewerke Hoechst AG Scholz, and Weigand, (1972a) W 17411 = 2-carbomethoxyamino benzimidazole toxikologischePrufung. 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(1973) Uptake and translocation of benomyl and carbendazim (methyl benzimidazole-2-yl carbamate) in the symplast. Pest. Sci. 4: 713 Solel, Z. and Edgington, L.V. (1973) Transcuticular movement of 1973 fungicides. Phytopathology, 63: 505 Zeller, H.,and Kirsch, P. (1971a) Acute oral toxicity of methyl-2-benzimidazole carbamate to the dog. Unpublished report submitted by BASF AG Zeller, H. and Kirsch, P. (1971b) Acute oral toxicity of methyl-2-benzimidazole carbamate to the rabbit. Unpublished report submitted by BASF AG
See Also: Toxicological Abbreviations Carbendazim (EHC 149, 1993) Carbendazim (HSG 82, 1993) Carbendazim (ICSC) Carbendazim (Pesticide residues in food: 1976 evaluations) Carbendazim (Pesticide residues in food: 1977 evaluations) Carbendazim (Pesticide residues in food: 1978 evaluations) Carbendazim (Pesticide residues in food: 1983 evaluations) Carbendazim (Pesticide residues in food: 1985 evaluations Part II Toxicology) Carbendazim (Pesticide residues in food: 1995 evaluations Part II Toxicological & Environmental) Carbendazim (Pesticide residues in food: 1995 evaluations Part II Toxicological & Environmental) Carbendazim (JMPR Evaluations 2005 Part II Toxicological)