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Kanji Ishikawa,* Itsuki OKUDA ** and Shozo KUWATSUKA

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Kanji Ishikawa,* Itsuki OKUDA ** and Shozo KUWATSUKA Agr. Biol. Chem., 37 (1), 165•`173, 1973 Metabolism of Benthiocarb (4-Chlorobenzyl N ,N- Diethylthiolcarbamate) in Mice•õ Kanji IsHIKAwA,*Itsuki OKUDA** and Shozo KUWATSUKA Faculty of Agriculture, Nagoya University , Nagoya, Aichi-ken *Life Science Research Institute , Kumiai Chemical Ind. Co., Ltd., Kikugawa-cho, Shizuoka-ken **Shimizu Factory , Kunnai Chemical Ind. Co., Ltd., Shibukawa, Shimizu, Shizuoka-ken Received July 19, 1972 Benthiocarb labeled at benzyl methylene group with carbon-14 was synthesized and studied on the distribution, excretion and metabolism in white mice. Benthiocarb was rapidly translocated into organs after oral administration. Radioactive substances were also rapidly eliminated mainly into urine, slightly into feces and little into expiration. Major metabolites in urine were identified as 4-chlorohippuric and 4-chlorobenzoic acids, and small amounts of glucuronides of the latter acid and 4-chlorobenzyl alcohol were detected. Benthio carb was degraded in liver homogenates, in which the microsomal fraction showed the largest activity, and the degradation was accelerated by reduced NADP as the cofactor for the reac tion. N-Desethylbenthiocarb, bis(4-chlorobenzyl) mono- and di-sulfides, and 4-chlorobenzoic acid were identified in the incubation mixture of the liver homogenates. The main metabolic pathway in mice seemed to be as follows; parent benthiocarb and/or the N-desethylbentiocarb were hydrolyzed, and the produced 4-chlorobenzylmercaptan presumed to be oxidized finally to 4-chlorobenzoic acid, which then conjugated with glycine to produce 4-chlorohippuric acid. Benthiocarb, 4-chlorobenzyl N,N-diethyl- 4-Chlorobenzyl chloride was reacted with sodium thiolcarbamate, is a pre-emergence herbicide N,N-diethylthiolcarbamate to produce 14C-benthiocarb, which was purified till 99% in the radio-purity by thin (Saturn, trade name of Kumiai Chemical Ind. layer chromatography. Its specific activity was 8.27 Co., Ltd.), which has been used in recent few mCi/mmole. years to control weeds mainly in paddy fields, especially grasses such as barnyardgrass. Its Thiolcarbamates. Thiolcarbamates, listed in Table low toxicity to mice or rats was informed I, were synthesized by the following two methods: previously.1) However, the information of Method A2) the metabolism in animals has not been ob RR•LNH+ClOCSCH2C6H4X_??_ tained yet. On this account, 14C-benthiocarb RR•LNCOSCH2C6H4X+base-HCl Method B3) was synthesized and its metabolism in mice RR•LNH+COS+NaOH •¨ RR•¨NCOSNa+H2O was studied in vivo and in vitro. RR•LNCOSNa+ClCH2C6H4X •¨ RR•LNCOSCH2C6H4X+LNaCl Carbonyl sulfide was evolved from ammonium CHEMICALS AND METHODS thiocvanate.4) Labeled benthiocarb. 14C-Benthiocarb labeled at 4-Chlorobenzyl N,N-dietlrylcarbamate, by 118•` benzyl-methylene group was synthesized from 4- 126•Ž/mmHg with refractive index of 1.5177, was chlorobenzoic acid labeled at carboxyl group as the synthesized by the following reactions.5) starting substance and supplied by Daiichi Pure Chemi (C2H5)2NCOH+SO2Cl2 •¨ cals Co., Ltd. 14C-4-Chlorobenzoic acid was chlori (C2H5)2NCOCl+SO2+HCl nated with sulfonyl chloride into the acid chloride, (C2H5)2NCOCl+HOCH2C6H4Cl _??_ which was then reduced to 4-chlorobenzyl alcohol with (C2H5)2NCOOCH2C6H4Cl+pyridine-HCl lithium alminum hydride. The alcohol was converted 4-Chlorobenzyl N,N-diethyldithiocarbamate was syn into 4-chlorobenzyl chloride with sulfonyl chloride. thesized by following reactions.6) Pale-yellow liquid, boiled at 166•`167•Ž/0.05 mmHg with refractive •õ Studies on the Metabolism of Benthiocarb. Part I. index of 1.6234, was obtained. 166 K. ISHIKAWA, I. OKADA and S. KUWATSUKA TABLE I SYNTHETIC THIOLCARBAMATES (C2H5)2NH+CS2+NaOH •¨ tures (•Ž): column oven 190, inlet block 220 and (C2H5)2NCSSNa+H2O detector 240. Gas chromatographic column: 3 mm (C2H5)2NCSSNa+ClCH2C6H4Cl •¨ (i.d.) •~200cm spiral stainless column containing 3% (C2H5)2NCSSCH2C6H4Cl silicone SE-30 on 60•`80 mesh acid-washed Chrome Bis(4-chlorobenzyl) di-sulfide was synthesized )by sorb W pretreated with 0.3% polyethyleneglycol 20M. Marcker's method.7) Internal standard substance: benzyl N,N-diisopropyl Na2S.9H2O+S •¨ Na2S2 - dithiocarbamate. Na2S2+2ClCH2C6H4Cl _??_ For the detection of bis (4-chlorobenzyl) mono- and ClC6H4CH2SSCH2C6H4Cl di-sulfide, Microtek MT-220 gas chromatograph equipped with FPD 200AT flame photometric detector Needles from ethanol melted at 59•Ž. Bis(4-chlorobenzyl) sulfide was synthesized by with a sulfur filter (394 mƒÊ) and a 1mV recorder was used under the following condition. Gas flow Marcker's method.7) Na2S+2ClCH2C6H4Cl _??_ (ml/min): nitrogen (carrier gas) 75, hydrogen 55, oxygen 15 and air 50. Temperatures (•Ž): column ClC6H4CH2SCH2C6H4Cl oven 240, inlet block 260 and detector 165. Gas 4-Chlorohippuric acid was synthesized by the follow chromatographic column: 3mm (i.d.) •~100cm U- ing reactions.8) shaped glass column containing 10% Polyester FF on H2NCH2COOH+ClC6H4COCl+2NaOH •¨ 60-80 mesh acid-washed Chromosorb W. Chart ClC6H4CONHCH2COONa+NaCl+2H2O speed: 2mm/min. The incubation mixtures for the ClC6H4CONHCH2OONa+HCl •¨ determination of sulfide-metabolites consisted of ClC6H4NHCH2OOH+NaCl ten-fold amounts of each components compared with White scaly crystals from ethanol melted at 143•Ž. the above-described experiments, because the only 4-chlorobenzyl alcohol, 4-chlorobenzaldehyde, 4- small amounts of sulfide-metabolites were detected in chlorobenzoic acid, 4-hydroxybenzyl alcohol, 4-hydroxyb- the incubation mixtures. They were extracted with enzoic acid, nicotinamide, and (ƒÀ-ghicuronidase were equal amounts of ether three times. Ether extracts obtained from Tokyo Kasei Kogyo Co., Ltd., and were combined and dried with small amounts of reduced NAD and reduced NADP from Sigma Chemical anhydrous sodium sulfate. After ether was evaporated Co., respectively. mildly, one ml of acetone was added to dissolve the Gas chromatographic determination.9) Unlabeled residue. FiveƒÊ1 of the acetone solution was injected benthiocarb in in vitro experiments was determined by to the gas chromatograph. the following procedures. The ether solutions, ex tracted from the incubation mixtures, were collected Thin-layer chromatography . Chloroform or ether and dried with small amounts of anhydrous sodium extracts, obtained from in vivo and in vitro experiments, sulfate. After 1ml of the internal standard solution were concentrated and dissolved in one ml of ether. (50 ppm in n-hexane) was added, the solutions were An aliquot of the ether solution was spotted on a thin filtered and concentrated. An aliquot of the con layer plate of silicagel HF254 (E . Merck), 0.25mm of centrated solutions was injected into a gas chromato thickness, and one Id of 5% acetone solution of the graph conditioned to determine benthiocarb. Hitachi reference compounds , listed in Table II, was overlapped 063 gas chromatograph equipped with dual flame ioni on the spot. Then the plate was developed with each zation detector and a one mV recorder was used under of the following solvent systems to the distance of the following conditions. Gas flow (ml/min): nitrogen 13cm by the ascending method and airdried well. (carrier gas) 40, hydrogen 35 and air 260. Tempera The spots of the reference compounds were detected Metabolism of Benthiocarb in Mice 167 under irradiation of ultra-violet light (254mƒÊ) and 30mg of ƒÀ-glucuronidase were added to the solution, the radioactive ones were detected by X-ray radio the mixture was incubated at 37.5•Ž for 24hr.12) It autogram. Solvent systems: n-hexane, benzene, was acidified and extracted with ether in the same way n-hexane-diisopropyl ether-chloroform-acetic acid as above. An aliquot of each ether extract was put (10:10:10:1), benzene-ethanol-acetic acid (40:1:2) into a counting vial. Another aliquot was concentrated and n-hexane-diisopropyl ether-diethylamine (20:20:1). and chromatographed on a thin layer plate. Each metabolite on the plate marked by the radioauto Mice treated with labeled benthiocarb were housed gram was collected with silicagel into a counting vial in metabolic cages, and sacrificed at intervals by and the radioactivity was measured. decapitation. The brain, blood, heart, kidney and liver were dissected out as rapidly as possible into cold Measurement of the radioactivity. Ten ml of potassium chloride solution (0.9%). They were toluene or dioxane liquid scintillator were added into washed with the solution and homogenized with ten a counting vial containing a sample and mixed to fold weight of the potassium chloride solution in a dissolve the radioactive substances. The radioactivity Potter-Elvehjem homogenizer with Teflon pestle under was determined by liquid scintillation counting. cooling with ice. The homogenates were extracted Toluene liquid scintillator, consisted of 1.32g of 2,5- with chloroform three times. The residues were diphenyloxazole, 160ml of toluene and 80ml of acidified to pH 1.0 with 10% trichloroacetic acid and ethyleneglycol monomethylether, was used for the again extracted three times with chloroform. An measurement of the trapping solutions in the in vivo aliquot of each two chloroform solutions and residual experiments, and dioxane system, containing 6g of homogenates was pipetted into a counting vial to 2,5-diphenyloxazole, 0.27g of 1,4-bis[2-(5-phenyl- measure the radioactivity. oxazolyl)] benzene and 112g of naphthalene in one liter of dioxane, for the measurement of other samples, Metabolism in liver homogenates. Male dd-strain mice, abstained from food overnight,
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