• Applied Biological Chemistry
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• v.27 no.2
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• pp.64-72
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• 1984

Alachlor, 2-chloro-2, '6'-diethyl-N-(methoxymethyl) acetanilide, which had been incubated in the flooded paddy soils yielded 1-formyl-2,3-dihydro-7-ethylindole, 2,6-diethylaniline, 2,6-diethylacetanilide, 2,6-diethyl-N-(methoxymethyl) acetanilide, 2-hydroxy-2, '6'-diethyl-N-(methoxymethyl) acetanilide, and three unidentifiable compounds as its degradation products. The water-soluble products of Alachlor in soil suspensions increased with incubation periods and similar results were obtained from the incubation of Rhizoctonia solani, as verified by use of the ring $-^{14}C-$labeled Alachlor. Streptomyces lavendulae Ru 3340-8 produced 2-hydroxy-2, '6'-diethyl-N-(methoxymethyl) acetanilide as the major degradation product as much as 25%, whereas Bacillus brevis IFO 3331, Bacillus cruciviae, and Pseudomonas putida did not produce it.

• Environmental Analysis Health and Toxicology
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• v.16 no.3
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• pp.133-137
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• 2001

Acetanilide is a High Production Volume Chemical, which is produced about 2,300 tons/year in Korea as of 1998 survey. Most is used as an intermediate for synthesis of pharmaceuticals and dyes and the chemical is one of seven chemicals of which human and environmental risks are being assessed by National Institute of Environmental Research under the frame of OECD SIDS program. The chemical is water soluble (4 g/1 at 20$\^{C}$) and readily biodegradable (68.7％). Partition coefficiency (Log Pow) is 1.16 at 23$\^{C}$ so that the chemical has a low potential for bioaccumulation. The acute toxicities of algae, daphnia and fish are not high. The 72 hr-EｂC50 of algae is 13.5 mg/1,48 hr-EC50 of daphnia is over 100 mg/1 and 96 hr-LC50 of Oryzias latipes is over 100mg/1. Regarding the exposure, levels in air, water, soil or sediment have not been monitored or estimated so that risk evaluation of acetanilide was not possible. In this study, distribution of the chemical among environmental media was estimated using EQC model based on the chemical-physical properties. In Level I and IIof which the chemical are hypothesized in equilibrium and no transfer through the media, more than 98％ of acetanilide are estimated to be distributed in water. However, in Level Ⅲ of which non-equilibrium and intermedia transfer could be occurred, the chemical is estimated to distributed to soil as 51.8％ and water as 47.8％ as of total amount.

• YAKHAK HOEJI
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• v.32 no.5
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• pp.295-303
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• 1988

For microbial production of acetaminophen, a popular analgesic-antipyretic from aniline, we screened various fungi and bacteria. And we succeeded to some extents in acetaminophen production by successful protoplast fusion between S. lividans and S. globisporus and also between S. rimosus and S. aureofaciens. However, more fertile results might be brought via performing the cloning of acetanilide p-hydroxylation genes of Streptomyces in yeast. This study was initiated to determine whether the acetanilide p-hydroxylase of Streptomyces is cytochrome P-450 species or non-heme iron protein species. The p-hydroxylationactivity on acetanilide in S. aureofaciens ATCC 10762 was found to be unstable on exposing to the air. However, 100,000xg supernatant of the cell free extracts which were prepared in $N_2$ atmosphere showed the p-hydroxylation activity. Characteristic absorption peak of cytochrome P-450 after reduction with dithionite and addition of CO was not observed in the region of 450nm. Moreover, metyrapone and 2, 6-dichloroindophenol did not affect this enzyme activity, but sodium azide, sodium cyanide, cupric sulfate, cadmium chloride, ${\alpha}$, ${\alpha}'-dipyridyl$, and o-phenanthroline reduced p-hydroxylase activity considerably. S. fradiae NRRL 2702 was shown to have strong p-hydroxylation activity in intact cells. This activity disappeared in its cell free extracts. In its 100,000xg supernatant, however, characteristic absorption peak of cytochrome P-450 after reduction with dithionite and addition of CO was observed at 446nm. Thus, the results herein presented suggest that acetanilide p-hydroxylase of Streptomyces aureofaciens is not related to cytochrome P-450 and may include non-heme iron protein for its activity. However, it is not clear whether acetanilide p-hydroxylase in S. fradiae belongs to the same category of S. aureofaciens.

• Environmental Analysis Health and Toxicology
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• v.16 no.3
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• pp.139-142
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• 2001

Acetanilide is a High Production Volume Chemical, which is produced about 2,300 tons/year in Korea as of 1998 survey. Most is used as an intermediate for synthesis of pharmaceuticals and dyes, and the chemical is one of seven chemicals of which human and environmental risk are being assessed by National Institute of Environmental Research under the frame of OECD SIDS program. The Atmospheric Oxidation Program for Microsoft Windows (AOPWIN) is used to estimates the rate constant for the atmospheric, gas－phase reaction between photochemically produced hydroxyl radicals and organic chemicals. It is also used to estimates the rate constant for the gas－phase reaction between ozone and olefinic/acetylenic compounds. The rate constants estimated by the program are then used to calculate atmospheric half－lives for organic compounds based upon average atmospheric concentrations of hydroxyl radicals and ozone. AOPWIN requires only a chemical structure to make these predictions. Structures are entered into AOPWIN by SMILES (Simplified Molecular Input Line Entry System) notations. In this study, one of environmental fate/distribution of the chemical elements, photodegradation of acetanilide was estimated using AOPWIN model based on SMILES notation and chemical name data.

• Journal of The Korean Society of Clinical Toxicology
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• v.9 no.2
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• pp.49-55
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• 2011

Purpose: Acetanilide has been in widespread use as an amide herbicide compound. However, available data regarding acute human poisoning is scarce. The aim of this study was to analyze the clinical characteristics of acetanilide poisoning in order to identify the risk factors associated with severity. Methods: We conducted a retrospective observational study encompassing the period January 2005 to December 2010, including adult ED patients suffering from acetanilide intoxication. Toxicological history, symptoms observed, clinical signs of toxicity, and laboratory test results were collected for each patient. The patients were classified into two groups for analysis, according their poisoning severity score (PSS). Resulting clinical data and prognostic variables were compared between mild-to-moderate poisoning (PSS 1/2 grades), and severe poisonings and fatalities (PSS 3/4 grades). Results: There were a total of 37 patients, including 26 alachlor, 6 s-metolachlor, 4 mefenacet, and 1 butachlor cases. The majority of patients (81.1%) were assigned PSS 1/2 grades. Changes in mental status and observation of adverse neurologic symptoms were more common in the PSS 3/4 group. The median ingested volume of amide herbicide compound was 250 ml (IQR 200-300 ml) in the PSS 3/4 group, and 80 ml (IQR 50-138 ml) in the PSS 1/2 group. Also, the median GCS observed in the PSS 3/4 group was 13 (IQR 10-14), which was markedly low as compared to a median GCS of 15 in the PSS 1/2 group. Overall mortality rate was 5.4%, and profound cardiogenic shock was observed prior to death in all fatalities. Conclusion: When compared to previous reports, acute acetanilide poisoning resulted in relatively moderate severity. The presence of neurologic manifestations, hypotension, lower GCS score, and larger ingested volumes was associated with more serious effects and mortalities.

• Toxicological Research
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• v.18 no.1
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• pp.13-22
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• 2002

In Korea, 2,320 tonnes of acetanilide were mostly wed as intermediates for synthesis in phar-maceuticals or additives in synthesizing hydrogen peroxide, varnishes, polymers and rubber. Only small amount of 120 kg were wed as a stabilizer for hydrogen peroxide solution for hair colouring agents in 1998. Readily available environmental or human exposure data do not exist in Korea at the present time. However, potential human exposures from drinking water, food, ambient water and in work places are expected to be negligible because this chemical is produced in the closed system in only one company in Korea and the processing factory is equipped with local ventilation and air filtering system. Acetanilide could be distributed mainly to water based on EQC model. This substance is readily biodegradable and its bioaccumulation is low. Acute toxicity of acetanilide is low since the L $D_{50}$ of oral exposure in rats is 1,959 mg/kg bw. The chemical is not irritating to skin, but slightly irritating to the eyes of rabbits. horn repeated dose toxicity, the adverse effects in rats were red pulp hyperplasia of spleen, bone marrow hyperplasia of femur and decreased hemoglobin, hematocrit and mean corpuscular hemoglobin concentration. The LOAEL for repeated dose toxicity in rats was 22 mg/kg/day for both sexes. Acetanilide is not considered to be genotoxic. In a reproductive/developmental toxicity study, no treatment-related changes in precoital time and rate of copulation, impregnation, pregnancy were shown in all treated groups. The NOAELs for reproduction and developmental toxicity (off-spring toxicity) are considered to be 200 mg/kg bw/day and 67 mg/kg bw/day, respectively. Ecotoxicity data has been generated in a limited number of aquatic species of algae (72 hr- $E_{b}$ $C_{50}$; 13.5 mg/l), daphnid (48hr-E $C_{50}$ > 100 mg/l) and fish (Oryzias latipes, 96hr-L $C_{50}$; 100 mg/l). Form the acute toxicity values, the predicted no effect concentration (PNEC) of 0.135 mg/1 was derived win an assessment factor of 100. On the basis of these data, acetanilide was suggested as currently of low priority for further post-SIDS work in OECD.in OECD.D.

• Environmental Analysis Health and Toxicology
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• v.15 no.1_2
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• pp.19-29
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• 2000

Acetanilide may be released into the environment through air and wastewater from its production and use sites as an intermediate in the synthesis of pharmaceuticals and dyes. Acetanilide is biodegraded rapidly under aerobic conditions and decomposed by indirect photolysis in the presence of OH radicals. An estimated bioconcentration factor of 4.5 suggests that bioaccumulation in aquatic organisms is low. Ecotoxicological data on acetanilide exist on acute toxicity to fishes of 4 species only. According to the EUSES system, the lowest PNEC (Predicted no effect concentration) in fishes is 0.01 mg/1 and PEC (Predicted environmental concentration) for surface water on a regional scale is 9.1$\times$10$\^$－5/mg/l as the worst case. RCR (Risk characterization ratio) of acetanilide for surface water on a regional scale was estimated as 9.1$\times$10-3, which is safe enough for fishes, RCR on a local basis slightly exceeds the value 1 in water and sediment; that is, 1.3 and 1.6, respectively, which suggests the existence of ecotoxicological risk at the vicinity of the manufacturing site. For the refinement of environmental risk assessment on acetanilide, more data should be collected regarding prolonged fish toxicity, acute toxicity toward daphnia and algae. It is, therefore, recommended that acetanilide should be a candidate for further work to supplement the lacking data until it is proved to be safe in the ecotoxicological aspects.

• Korean Journal of Environmental Agriculture
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• v.3 no.1
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• pp.1-9
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• 1984

Two of the degradation products of alachlor in soil. product 1, 2,6-diethyl-N-(methoxymethyl) acetanilide and product 2,2-hydroxy-2',6'-diethyl-(methoxymethyl) acetanilide were synthesized from alachlor reacting with 3N-hydrochloric acid in the presence of zinc powder at room temperature and a saturated sodium bicarbonate solution at $90^{\circ}C$ for 78 hr, respectively. At the concentrations of both $5{\times}10^{-4}M\;and\;1{\times}10^{-3}M$, product 2 exhibited almost the same phytotoxicity to rice seedlings, in particular, as alachlor, whereas product 1 lost its phytotoxic effectiveness. It seems that substitution of chlorine atom by hydroxyl group did not affect the phytotoxicity of alachlor, whereas substitution by hydrogen atom did.

• Environmental Analysis Health and Toxicology
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• v.16 no.4
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• pp.223-226
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• 2001

Acetanilide is a High Production Volume Chemical, which is produced about 2,300 tons/year in Korea as of 1998 survey. Most is used as an intermediate for synthesis of pharmaceuticals and dyes. The chemical is one of seven chemicals, which are under the frame of OECD SIDS program sponsored by National Institute of Environmental Research of Korea. Regarding the information on the environmental fate. bioconcentration is one of important factor to estimate the environmental tranfer. However, measurement of bioconcentration needs high expense and time. For this reason, OECD recommends to use BCFWIN model to estimate bioconcentration of organic chemicals, BCFWIN estimates the bioconcentration factor (BCF) of an organic compound using the log octanol-water partition coefficient (Kow) of the compound. Structures are entered into BCFWIN through SMITES (Simplified Molecular Input Line Entry System) notations. The BCFWIN method classifies a compound as either ionic or non-ionic. ionic compounds include carboxylic acids, sulfonic acids and salts of sulfonic acids, and charged nitrogen compounds (nitrogen with a + 5 valence such as quaternary ammonium compounds). All other compounds are classified as non-ionic. In this study, bioaccumulation of acetanilide was estimated using BCFWIN model based on SMIIES notation, chemical name data and partition coefficient as one of environmental fate/distribution of the chemical elements.

• Environmental Analysis Health and Toxicology
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• v.15 no.1_2
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• pp.31-37
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• 2000

Acetanilide may be released into the environment through air and wastewater from its production and use sites and exposed to human. Acetanilide is known to produce an analgesic effect and may pose adverse effects on human health by overly exposure. According to the EUSES system, acetanilide showed a high MOS (Margin of safety) value exceeding 6$\times$10$^4$ on a regional exposure, which is safe enough for public health. Whereas the lowest MOS value in dermal exposure was estimated as 3$\times$10$^{-4}$ on a local basis (workplace), the risk could be partly counteracted by taking preventive measures such as using mask and globes and good ventilation in the work places. Acetanilide may pose a potential risk for workers by dust inhalation. For the sake of health protection in the work places, additional data should be accumulated with respect to repeated dose toxicity, reproduction toxicity and developmental toxicity, etc. It is, therefore, recommended that acetanilide should be a candidate for further work to supplement the lacking data until it is proved to be safe in the occupational health aspects.