• Applied Biological Chemistry
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• v.26 no.1
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• pp.53-57
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• 1983

Butachlor incubated for certain periods of time under the simulated, rather aerobic, rice-paddy conditions of two different soils exhibited two major degradation products. 2,6-diethyl-N-(butoxymethyl) acetanilide and a new product C in all cases, and a relativly small amount of another new product D named tentatively as 8-ethyl-2-hydroxy-N-(butoxymethyl)-3,4-dihydroquinoline in some cases. The supposedly microbial degradation seemed to proceed with incubation periods to some extent. An anaerobic incubation in the previous investigation showed 2,6-diethyl-N-(butoxymethyl) acetanilide as the major product, whereas the new product C with m/z 291 turned out to be the major one in the present condition. Structural elucidation of the products was done based on the fragmentation patterns of the given mass spectra and a possible pathway for their formation was postulated.

• Applied Biological Chemistry
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• v.29 no.2
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• pp.182-189
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• 1986

Alachlor, 2-chloro-2',6'-diethyl-N-(methoxymethyl) acetanilide produced four major degradation products, when incubated under an upland soil condition for 80 days. They include 8-ethyl-2-hydroxy-N-(methoxymethyl)-1,2,3,4-tetrahydroquinoline (m/z 221), N-hydroxyacetyl-2,3-dihydro-7-ethylindole (m/z 205), 2-hydroxy-2',6'-diethyl-N-(methoxymethyl) acetanilide (m/z 251), and 9-ethyl-1,5-dihydrol-(methoxymethyl)-5-methyl-4,1-benzoxazepin-2 (3H)-one (m/z 249). The products turned out to be a little different from those obtained under the flooded paddy soil condition used in the previous paper. The plausible pathways for the degradation were proposed.

• Archives of Pharmacal Research
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• v.15 no.3
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• pp.215-219
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• 1992

S. fradiae exhibited the highest acetanilide p-hydroxylation activity among the Streptomyces spp. screened. Studies with inhibitors (metyrapone, 2. 6-dichloroindophenol, $\alpha,\alpha'$-dipyridyl, o-phenanthroline) and an absorption peak after CO treatment suggested that S. fradiae hydroxylase activity was due to cytochrome p-450. This hydroxylase activity was increased to ten times in the cell extract containing 0.5 mM sodium azide. Furthermore, the sedimentary activity in $105,000\times{g}$ centrifugal forces and solubilization of the activity with Triton-X 100 implied that this enzyme was membrane bound monooxygenase. pH Optimum of the enzyme was 6.5 in membrane bound state.

• Archives of Pharmacal Research
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• v.15 no.1
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• pp.35-40
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• 1992

S. fradiae showed the highest acetanilide p-hydroxylation activity in the tested strains. And S. fradiae was well characterized genetically, especially with respect to tylosin production. Two mutants, which lost hydroxylation, were isolated in 140 regenerated colonies from protoplasts. In restriction enzyme digesion of total DNAs, isolation of giant linear plasmid DNA and determination of antibiotic resistances to chloramphenicol, tylosin, hygromycin B and mitomycin C, any differences among mutants and a wild type strain were not detected. These facts suggest that lesion on 6, 000 Kb chromosomal DNA was responsible for the lack of p-hydroxylation activity induced by protoplast formation and regeneration.

• YAKHAK HOEJI
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• v.33 no.3
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• pp.156-160
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• 1989

A gas-chromatographic determination method of thiamin which use a quantitative cleavage of thiamin to 4-methyl-5-(2-hydroxyethyl)thiazol [I] and solvent extraction of the analyte prior to GC injection was modified. A column chromatographic procedure using a reversed phase, high capacity solid phase cartridge was applied to the clean-up of the analyte. Thiazol derivative[I] was quantitatively recovered upon the column method. Acetanilide, an internal standard, has a good recovery through the analytical procedure. The method has analytical precision of 2% or less in the coefficient of variation.

• Applied Biological Chemistry
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• v.25 no.2
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• pp.83-92
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• 1982

In an anaerobic incubation of uniformly ring-labeled $^{14}C-butachlor$ in two Korean soils for 3 months, very little $^{14}CO_2$ and volatile products were measured. In soil A, 77.52 and 45.36% of the sterile and viable soil radioactivity, respectively, were methanol-extractable and the rest were adsorbed in soil; whereas in soil B, 58.85 and 37.23%, respectively, were methanol-extractable and the rest remained in soil. The adsorption of $^{14}C-butachlor$ depends on the characteristics of the soils. The major metabolite was 2,6-diethyl-N-(butoxymethyl) acetanilide. 2,6-Diethylaniline and 2,6-diethylacetanilide turned out to be the minor metabolites on GLC-MS.

• Toxicological Research
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• v.23 no.4
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• pp.391-403
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• 2007

The study was conducted to assess the repeated dose and reproduction and developmental toxicities of acetanilide, an intermediate for drug production, as a part of OECD Screening Information Data Set (SIDS) program. The test agent was administered by gavage at dose levels of 0, 22, 67, 200 and 600 mg/kg to Sprague-Dawley rats (12/group/sex) during pre-mating and mating period for males(up to 30 days) and females and pregnancy and early lactation period for females (up to 39-50 days). At 22 mg/kg, decreases in HGB, HCT (males) and MCHC (females), hyperplasia of spleen red pulp, hyperplasia of femur bone marrow (both sexes) were observed. At 67 mg/kg, salivation (males), reduced food consumption (both sexes), decreases in RBC, HGB, HCT and MCHC (males), increases in MCV (males) and spleen weight (males), hyperplasia of spleen red pulp and femur bone marrow (both sexes) were observed. At 200 mg/kg, decreases in locomotor activity and salivation (both sexes), reduced food consumption (both sexes), decreases in RBC, HGB, HCT and increases in MCV, MCH, BUN, T-BIL (males), enlargement of spleen (both sexes), increased weight of spleen (males), hyperplasia of spleen red pulp and femur bone marrow and extramedullary hematopoiesis of liver (both sexes), atrophy of thymus and corpus luteum hyperplasia of ovary (females) were observed. At 600 mg/kg, decreases in locomotor activity, cyanosis (both sexes), reddish tear, and salivation (males), mortality (4 out of 12 females), decreased body weight (females), reduced food consumption (both sexes), decreases in RBC, HGB, HCT and MCHC and increases in WBC, MCV, MCH, reticulocyte, neutrophil, lymphocyte, monocyte, AST, ALT, BUN, T-BIL, ALB, Ca and A/G ratio (males), enlargement of spleen, increased weights of spleen (both sexes), liver (males), kidney and ovary, decreased weights of thymus (females), hyperplasia of spleen red pulp, hyperplasia of femur bone marrow and extramedullary hematopoiesis of liver (both sexes), and atrophy of thymus and corpus luteum hyperplasia of ovary (females) were observed. Regarding the reproduction and development toxicities, there were no treatment-related changes in precoital time, mating index, fertility index and pregnancy index at all doses tested. At 22 and 67 mg/kg, there were no adverse effects on all the parameters observed. At 200 mg/ kg, decreased body weight of pups (day 4 p.p.) were observed. At 600 mg/kg, decreased body weight of pups (day 0 and 4 p.p.) and viability index (day 4 p.p.), increased incidence of newborns dead or with abnormal clinical signs were observed. The results suggest that the NOAELs for general toxicity are < 22 mg/kg, LOAELs are 22 mg/kg and the NOAELs for reproductive toxicity are 67 mg/kg.

• Bulletin of the Korean Chemical Society
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• v.23 no.10
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• pp.1359-1360
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• 2002

• Applied Biological Chemistry
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• v.20 no.3
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• pp.310-316
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• 1977

The adsorption of 2-Chloro-4-(ethylamino)-6-(isopropylamino)-s-trazine (Atrazine) and 2-Chloro-2' 6' diethyl-N(methoxymethyl)acetanilide(Alachlor) by 21 Korean surface soils is studied and discussed in relation to some properties of soils. 1. Adsorption of Atrazine was correlated posisively with content of clay and organic matter, but negatively with extractable potassium content and sand content. 2. Adsorption of Alachlor was correlated positively with organic matter, caly content and CEC, but negatively with sand content 3. Isothermal adsorpsion of Alachlor was confirmed to the Freundlich eguation.

• Bulletin of the Korean Chemical Society
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• v.23 no.9
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• pp.1208-1254
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• 2002

Photoreaction of N-(o-halophenyl)acetamide in basic acetonitrile produces an intramolecular substituted product, 2-methylbenzoxazole in addition to reduced product, acetanilide, whereas photoreaction of N-(o-halobenzyl) acetamide affords a reduced product, N-benzylacetamide only. On the basis of preparative reaction, kinetics, and UV/vis absorption behavior, an electrophilic aromatic substitution of aryl halide with oxygen of its amide bond are proposed.