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PubMed2003

General fugacity-based model to predict the environmental fate of multiple chemical species.

A general multimedia environmental fate model is presented that is capable of simulating the fate of up to four interconverting chemical species. It is an extension of the existing equilibrium criterion (EQC) fugacity model, which is limited to single-species assessments. It is suggested that multispecies chemical assessments are warranted when a degradation product of a released chemical is either more toxic or more persistent than the parent chemical or where there is cycling between species, as occurs with association, disassociation, or ionization. The model is illustratively applied to three chemicals, namely chlorpyrifos, pentachlorophenol, and perfluorooctane sulfonate, for which multispecies assessments are advisable. The model results compare favorably with field data for chlorpyrifos and pentachlorophenol, while the perfluorooctane sulfonate simulation is more speculative due to uncertainty in input parameters and the paucity of field data to validate the predictions. The model thus provides a tool for assessing the environmental fate and behavior of a group of chemicals that hitherto have not been addressed by evaluative models such as EQC.

Alkanesulfonic Acids↗
PubMed1985

Major role of hepatic sulfotransferase activity in the metabolic activation, DNA adduct formation, and carcinogenicity of 1'-hydroxy-2',3'-dehydroestragole in infant male C57BL/6J x C3H/HeJ F1 mice.

1'-Hydroxy-2',3'-dehydroestragole is a synthetic acetylenic analogue of 1'-hydroxyestragole, the proximate carcinogenic metabolite of the naturally occurring hepatocarcinogen estragole (1-allyl-4-methoxybenzene). This analogue is considerably more potent than 1'-hydroxyestragole as an hepatocarcinogen in mice. 1'-Acetoxy-2',3'-dehydroestragole reacted readily with deoxyguanosine or deoxyguanosine 5'-monophosphate at neutrality to form two adducts. Adduct I, isolated and characterized after dephosphorylation of the deoxyguanosine 5'-monophosphate product, was a 1:1 mixture of two diastereomers of N2-(2',3'-dehydroestragol-1'-yl)deoxyguanosine. Adduct II was shown to be N-7-(2',3'-dehydroestragol-1'-yl)guanine. The reaction of deoxyadenosine with 1'-acetoxy-2',3'-dehydroestragole at neutrality produced Adducts III and IV. Adduct IV was characterized as N6-(2',3'-dehydroestragol-1'-yl)deoxyadenosine. Administration of [1'-3H]-1'-hydroxy-2',3'-dehydroestragole to male preweanling C57BL/6J x C3H/HeJ F1 (hereafter called B6C3F1) mice resulted in extensive covalent binding to hepatic DNA, RNA, and protein. On hydrolysis of the DNA to nucleosides, a single major adduct accounted for greater than 85% of the DNA-bound 3H. This adduct comigrated with Adduct I in two high performance liquid chromatography systems, had a pH partition profile identical to that of Adduct I, and was present as a mixture of diastereomers in a ratio of 2:1. The identity of the DNA adduct formed in vivo with Adduct I from the reaction of 1'-acetoxydehydroestragole indicated that a reactive ester was a major metabolic precursor in vivo. There was no significant loss of Adduct I from the hepatic DNA by 21 days after a single injection of a carcinogenic dose of 1'-hydroxy-2',3'-dehydroestragole. Adducts II, III, and IV were not detected in significant amounts in the hepatic DNA isolated by a phenol extraction method or by a more rapid hydroxylapatite method. Cytosolic sulfotransferase activity was demonstrated for 1-hydroxy-2',3'-dehydroestragole in mouse liver, and inhibition of this activity by greater than 95% was found on addition of 10 microM pentachlorophenol. The administration of pentachlorophenol (0.04 mumol/g body weight) 45 min prior to a single dose of 1'-hydroxy-2',3'-dehydroestragole (0.04 mumol/g body weight) in 12-day-old male B6C3F1 mice greatly inhibited (87-97%) the covalent binding of 1'-hydroxy-2',3'-dehydroestragole to hepatic macromolecules and the formation of hepatomas at 10 months.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗
PubMed1978

Side reactions in peptide synthesis. IX. Suppression of the formation of aminosuccinyl peptides with additives.

The base-catalyzed ring closure of beta-benzylaspartyl peptides was efficiently suppressed by the addition of phenols (with electron-withdrawing substituents) to the reaction mixtures. From a series of compounds tested, 2,4-dinitrophenol and pentachlorophenol were the most effective. No direct relationship was found between the acidity of the additives and their ability to suppress the formation of aminosuccinyl peptides. The applicability of 2,4-dinitrophenol and pentachlorophenol in practical syntheses was also examined.

Acylation↗
PubMed2006

Use of multivariate analysis for optimization of separation parameters and prediction of migration time, resolution, and resolution per unit time in micellar electrokinetic chromatography.

The optimization of separation parameters in chromatography for better separation and resolution of analytes continues to be a labor intensive procedure usually performed by a trial and error method. A multivariate analysis in the form of multilinear regression (MLR) is used to optimize separation parameters and predict the migration behavior, resolution, and resolution per unit time of achiral (4-chlorophenol, pentachlorophenol, clonazepam, and diazepam) and chiral (1,1'-binaphthyl 2,2'-dihydrogen phosphate (BNP), and 1,1'-bi-2-naphthol (BOH)) compounds in MEKC. Separations of achiral and chiral analytes were performed using an achiral (poly(sodium N-undecylenic sulfate)) molecular micelle and chiral (poly(sodium N-undecanoyl-L-leucylvalinate) or poly(sodium N-undecanoyl-L-isoleucylvalinate)) molecular micelle, respectively, at various operating temperatures, applied voltages, pH values, and molecular micelle concentrations in the BGE. The separation parameters were subsequently used as input variables for MLR models. The models were validated with independent samples. The root-mean-square percent relative error (RMS%RE) is used as a figure of merit for characterizing the performance of the migration time, resolution, and resolution per unit time models. The RMS%RE obtained for predicted migrated times, resolutions, and resolution per unit time of 4-chlorophenol, pentachlorophenol, clonazepam, diazepam, BNP, and BOH ranged between 8 and 19%. The same experimental procedure was used to optimize the separation parameters of six other chiral analytes of different compound class. The predicted migration times, resolutions, and resolution per unit time of the chiral as well as the achiral analytes compare favorably with the experimental migration times and resolutions, indicating versatility and wide applicability of the technique in MEKC.

Chromatography, Micellar Electrokinetic Capillary↗
PubMed1991

[Residues of organochlorine pesticides, PCB's and chlorophenols in fish from commercial ponds and fish hatcheries from the waters in the area of Frankfurt (Oder)].

Fishes from fish-hatcheries, lakes and the river Oder in the area of the former district Frankfurt (Oder) were analysed for organochlorine pesticides (HCB, aldrin, HCH-isomeres, DDD, DDE, DDT, endrin, toxaphen and dieldrin), polychlorinated biphenyles and penta- and tetrachlorophenole. A clean up-procedure using acidic digestion mixture has been compared with a column-extraction-procedure followed by column chromatography on aluminia. Furthermore the simultaneous determination of the organochlorine pesticides, PCB's and chlorophenoles by acidic silicagel-extraction is described. The identification and quantification was realized by packed-column and capillary-gaschromatography including electron-capture-detection. The investigations show, that the permissible levels were only reached up to 2 to 10% with exception of toxaphen and pentachlorophenole. Average 50% of the toxaphen- and pentachlorophenole-values were found near the tolerance levels settled for these substances. The application of both substances in the area of the former German Democratic Republic until today can be regarded as a reason for this. The results of our investigations are comparable to last publications on fish contamination in the area of the previous Federal Republic of Germany.

Animals↗
PubMed1994

Biotests using unicellular algae and ciliates for predicting long-term effects of toxicants.

Test systems for predicting long-term effects with the freshwater algae Chlamydomonas reinhardi and Scenedesmus subspicatus and the ciliate Tetrahymena pyriformis were evaluated with respect to the following reference chemicals: atrazine, bromacil, diuron, methyl parathion, lindane, 3,4-dichloroaniline, pentachlorophenol, cadmium, copper, and the volatile 1,2-dichloropropane. In growth-inhibition tests under static conditions the algae revealed a higher sensitivity to the toxicants than the ciliate except for lindane and methyl parathion. Comparison of the impairment of photosynthetic efficiency (EPR, NOEC 24 hr) with the inhibition of growth (NOEC 72 hr) of S. subspicatus revealed a higher sensitivity of the EPR parameter for inhibitors of the photosynthesis. A flowthrough system was developed for long-term tests and testing of volatile and instable substances. Under flowthrough conditions C. reinhardi was more susceptible to the chemicals than under static test conditions, except for pentachlorophenol. Due to the high volatility, 1,2-dichloropropane was only tested in the flowthrough system. The data obtained from these toxicity tests provide information about effects on organisms representing different levels of the aquatic food web, possessing differences in sensitivity against toxicants. The presented flowthrough system allows the testing of volatile and instable chemicals, problematic in static test systems, and the EPR parameter is suitable for the early characterization of chemicals acting as specific inhibitors of the photosynthetic electron transport chain.

Animals↗
PubMed1994

Toxic effects of pollutants on the mineralization of chloroform in river sediments.

The influence of pollutants on the formation of 14CO2 from 3 micrograms/liter labeled chloroform was studied in anaerobic Dutch river sediments. All incubations were performed under anaerobic conditions. Addition of toxicants to sediment microcosms showed logistic dose-effect curves. The concentration giving 10% inhibition of the chloroform mineralization rate (IC10) was derived from these dose-effect curves. The IC10 values of added cadmium, chloropyrifos, benzene, mercury, or 1,2-dichloroethane were 1300, 1300, 140, 90, and 0.07 mg/kg dry sediment, respectively. Mud samples taken at different dates from the same site indicated a significantly different sensitivity to added pentachlorophenol and zinc. The IC10 of added pentachlorophenol was 150 mg/kg in one and 15 mg/kg in another sample. Chloroform-mineralizing bacteria are very sensitive to addition of zinc. The IC10 of added zinc was 700 mg/kg for one sample and 11 mg/kg for another sample of the sediment which contained a background concentration of 800 mg Zn/kg. Therefore, a partial inhibition of the mineralization of chloroform by the high concentrations of zinc present in Dutch river sediments cannot be excluded. The high concentration of zinc might cause persistence of otherwise biodegradable pollutants in Dutch sediments.

Anaerobiosis↗
PubMed1995

Estimation of selected phenols in drinking water with in situ acetylation and study on the DNA damaging properties of polychlorinated phenols.

Gas chromatography/mass spectrometry with selected-ion monitoring (GC/MS-SIM) method were used to analyze 23 selected phenols in natural and drinking waters by an in situ acetylation technique. This method was suitable for determining phenol concentrations at the ng/L level because of less background interference and better recoveries. The application range for all these phenols was from 0.01 or 0.04 to 10 micrograms/L, using a 800 ml water sample. The levels of trace phenols in four Taiwan water treatment plants were in the range of 12-312 ng/L. The polychlorinated phenols, namely 2,4,6-trichlorophenol, 2,3,4,6-tetrachlorophenol, and pentachlorophenol, were evaluated for their ability to induce deoxyribonucleic acid (DNA) damage using a DNA precipitation assay employing mouse embryonic fibroblast cells (C3H10T1/2) with or without a liver microsomal activation system. These agents exhibited a weak positive response when microsomal activation enzymes were present in this assay. When the tetrachlorohydroquinone, a toxic metabolite of pentachlorophenol, was measured by the same method without the activation system, a significant and dose-dependent DNA damage was found. This result indicates that in the evaluation of the carcinogenic potential of these agents, their corresponding metabolites should be taken into consideration. DNA strand breakage caused by these active metabolites may play an important role in the tumorigenetic process of polychlorinated phenols.

3T3 Cells↗
PubMedDate not supplied

Behavioral indicators of sublethal toxicity in rainbow trout.

Four measures of behavior--spontaneous swimming activity, swimming capacity, feeding behavior, and vulnerability to predation--were assessed as indicators of sublethal toxicity in rainbow trout (Oncorhynchus mykiss) in 96-hr exposures to sublethal concentrations of six agricultural chemicals: carbaryl, chlordane, dimethylamine salt of 2,4-dichlorophenoxyacetic acid (2,4-DMA), tributyl phosphorotrithioate (DEF), methyl parathion, and pentachlorophenol. After exposures, behavioral changes consistently demonstrated sublethal toxicity, but effects on specific behaviors varied with contaminants and their concentrations were altered by the water quality criterion concentration for chlordane (2 micrograms/L), and at a concentration of DEF (5 micrograms/L) that had previously been shown to inhibit growth and survival after a 90-day exposure. Feeding behavior was inhibited most by exposure to DEF, 2,4-DMA, and methyl parathion. Vulnerability to predation was heightened most by exposure to carbaryl and pentachlorophenol. Although all chemicals inhibited spontaneous swimming activity, only carbaryl, DEF, and 2,4-DMA influenced swimming capacity.

Animals↗
PubMed1977

Disturbance of microsomal detoxication mechanisms in liver by chlorophenol pesticides.

The pesticide pentachlorophenol known as an uncoupler of mitochondrial oxidative phosphorylation was shown to disturb liver microsomal detoxication functions by a selective inhibition of the terminal oxygenation enzyme P-450. At lower concentrations the flavin moiety of this enzyme chain is not inhibited but rather is stimulated, whereby a qualitative shift in detoxication of aromatic amines from C-oxygenation to N-oxygenation is obtained. The effects were due to the pentachlorophenol itself and not to a metabolite. Similar effects of varying strength were also obtained with other chlorophenol pesticides; 2,4,di-, 2,4,6,-tri and 2,3,4,6-tetrachlorophenol, di- and hexachlorophen, tri- and nonachloro-2-hydroxydiphenyl ethers. The relevance of these findings to the possible synergistic influence of chlorophenols on the carcinogenic effects of polyaromatic amines and hydrocarbons is discussed.

Aniline Compounds↗
PubMed1990

Interaction of chlorinated phenols with thyroxine binding sites of human transthyretin, albumin and thyroid binding globulin.

Previous results (Brouwer and van den Berg, Toxicol. Appl. Pharmacol., 85 (1986) 301) indicated preferential binding of a hydroxylated metabolite of tetrachlorobiphenyl to transthyretin (TTR) a carrier of thyroxine (T4). In the present study it was investigated whether the T4 binding site of TTR could be occupied specifically by hydroxylated chlorinated aromatic compounds using chlorinated phenol congeners as model compounds in a competition assay with [125I]T4. Chlorinated aromatics such as 2,3-dichlorobenzene and 3,4,3',4'-tetrachlorobiphenyl, and phenols such as 4-hydroxybiphenyl and phenol were inefficient competitors. All chlorinated phenols tested were competitors for the T4 binding site of TTR. The ranking in competition was pentachlorophenol (PCP) greater than trichlorophenols greater than dichlorophenols greater than monochlorophenols. Structures with chlorine in both ortho positions to the hydroxyl group were more efficient competitors. The relative affinity of binding of pentachlorophenol (PCP) to TTR was about twice that of T4. Scatchard analysis showed that PCP mainly decreased the affinity constant K11 while the binding capacity R1 was not altered, indicating a competitive type of inhibition. PCP was also able to compete with T4 sites on albumin with a relative affinity of 0.25. T4 binding to thyroid binding globulin (TBG) was much less affected by interference of PCP (relative affinity 0.001). The results indicate a specific interaction of chlorophenols with the T4 binding site of TTR.

Binding Sites↗
PubMed1991

Accumulation and depuration of chlorinated phenolics in the freshwater mussel (Anodonta anatina L.).

Uptake from ambient water and the depuration of five chlorinated phenolics, two chloroguaiacols (3,4,5-tri- and tetrachloroguaiacol), and three chlorophenols (2,4,6-tri-, 2,3,4,6-tetra-, and pentachlorophenol) were studied in the duck mussel (Anodonta anatina). Groups of animals were exposed at four acclimiation temperatures (3, 8, 13, 18 degrees C) to four chlorophenolic concentrations (total 6-56 micrograms/liter). The depuration was monitored for 72 hr. For the analysis of individual chlorophenolics by the GC/ECD technique, the soft tissue of mussels was homogenized, spiked with internal standard, acetylated, and extracted with n-hexane. The bioconcentration factors (BCF) (concn. in animal wet wt./concn. in water) were determined for mussel soft tissue. The highest BCF was found for pentachlorophenol (81-461) and the lowest for trichlorophenol (14-125). Neither water temperature nor exposure concentration affected the BCFs. The compounds studied were depurated rapidly and their depuration half-lives (T1/2) in soft tissue were generally less than 24 hr.

Animals↗
PubMed1991

Acute toxicity tests using rotifers. IV. Effects of cyst age, temperature, and salinity on the sensitivity of Brachionus calyciflorus.

Several aspects of the response to toxicants using a standardized toxicity test with the freshwater rotifer Brachionus calyciflorus are described. Test animals are obtained by hatching cysts which produce animals of similar age and physiological condition. The acute toxicity of 28 compounds is described with 24-hr LC50's. The LC50's span five orders of magnitude, from silver at 0.008 mg.liter-1 to benzene at more than 1000 mg.liter-1. Control mortality in 84 tests averaged 2% with a standard deviation of 3%, indicating very consistent test sensitivity. Only once in 84 trials did a test fail because of excessive control mortality, yielding a failure rate of 1.2%. Cyst age from 0 to 18 months had no effect on the sensitivity of neonates to reference toxicants. Both high and low temperatures increased rotifer sensitivity to reference toxicants. Copper sensitivity was greater at 10, 25, and 30 degrees C compared with results at 20 degrees C. Likewise, sodium pentachlorophenol toxicity was greater at 10 and 30 degrees C compared with results at 20 degrees C. Survivorship curves at 25 degrees C of neonates under control conditions indicated that mortality begins at about 30 hr. This places a practical limit on toxicant exposure for the assay of 24 hr. B. calyciflorus cysts hatch at salinities up to 5 ppt and acute toxicity tests using pentachlorophenol at this salinity yielded LC50's about one-half those of standard freshwater. B. calyciflorus is preferred over Brachionus plicatilis for toxicity tests in salinities up to 5 ppt because it is consistently more sensitive.

Animals↗
PubMed1992

Comparison of sublethal and lethal criteria for nine different chemicals in standardized toxicity tests using the earthworm Eisenia andrei.

In this study, the effects of nine different chemicals on the survival, growth, and reproduction of the earthworm species Eisenia andrei were determined using a recently developed method. Earthworms were exposed for 3 weeks to the test chemicals in an artificial soil substrate. Additional data on the acute toxicity of these chemicals were derived from the literature. For some chemicals, cocoon production was the most sensitive parameter (cadmium, chromium, paraquat, fentin, benomyl, phenmedipham), while for others cocoon hatchability was most sensitive (pentachlorophenol, parathion, carbendazim). In the case of parathion, growth of the worms seemed to be even more sensitive than reproduction. As an overall parameter for the effect on earthworm reproduction, the total number of juveniles produced per worm appeared to be a useful parameter. Differences between (acute) LC50 values and the lowest NOEC value for effects on growth and reproduction were different for each chemical. Difference was greatest for cadmium (a factor of greater than 100) and smallest for fentin, benomyl, and pentachlorophenol (a factor of 5-6).

Animals↗
PubMed1985

The transformation of chlorophenols by lactoperoxidase.

The lactoperoxidase-catalyzed transformations of penta-,2,3,4,6-tetra-, 2,4,6-tri-, 2,4-di- and 4-monochlorophenol were followed spectrophotometrically. Apparent stoichiometries of chlorophenol:H2O2 ranged from 1:1 for the tri- and tetrachlorophenol at pH7 to 5:2 for pentachlorophenol at pH 4. The initial velocity (v0) was only slightly influenced by changes in [H2O2] greater then 5 microns. v0 responded to [chlorophenol] according to the empirical expression v0=[lactoperoxidase] . (k1[chlorophenol] + k2[chlorophenol]2). The constant k1 was trichlorophenol, respectively, at pH 7. With the di- and monochlorophenol the solution soon became opaque, and the reaction ceased. The results show that more than one reaction occurs. Some comparisons were also made with horseradish peroxidase A and C. Cetyltrimethylammonium bromide prevented opaqueness, but was shown to be a substrate for lactoperoxidase. Assuming an average concentration of 0.1 microns for H2O2 and pentachlorophenol in man, the metabolic rate becomes 30 ng/h per g of peroxidase-containing tissue, possibly with deposition of the products.

Animals↗
PubMed1986

Metabolism of hexachlorobenzene (HCB) in the isolated perfused rat liver.

The metabolism of HCB in the isolated perfused rat liver was studied by administration of [14C]HCB diluted with unlabelled HCB at a total dose of 0.1 mg HCB/ml perfusate. Metabolites in bile, perfusate and liver were studied by GLC-mass spectrometry. Histological examination of the livers showed that no hepatic necrosis had developed, although there was a slight increase in ASAT and ALAT in the perfusate and about 50% decrease in hepatic glutathione. About 0.15% of administered radioactivity was recovered in the bile within 2 hr. In the bile, HCB together with the metabolites pentachlorothiophenol and pentachlorophenol, were identified and accounted for about 20% of the radioactivity excreted. In addition, eleven metabolites with 4 or 5 chlorines were isolated. In the perfusate and in the liver, unchanged HCB was responsible for most of the radioactivity. Traces of pentachlorothiophenol and pentachlorophenol were identified in the perfusate and the liver, respectively.

Animals↗
PubMed2006

Levels of chlorinated compounds (CPs, PCPPs, PCDEs, PCDFs and PCDDs) in soils at contaminated sawmill sites in Sweden.

Soil samples from five contaminated sawmill sites in Sweden were characterized with respect to chlorophenols (CP), chlorinated phenoxy phenols (PCPP, hydroxylated chlorinated diphenyl ethers), chlorinated diphenyl ethers (PCDE), chlorinated dibenzofurans (PCDF) and chlorinated dibenzo-p-dioxins (PCDD). The composition of chlorinated compounds in the soil samples was compared to the composition of two preservatives commonly used in the Scandinavian wood impregnation industry: the 2,3,4,6-tetrachlorophenol preservative called Ky-5 and the pentachlorophenol preservative Dowicide G. The levels of CPs in the soil samples ranged from 0.1 to 4500 mgkg-1 d.w., PCPPs from <0.15 to 940 mgkg-1 d.w., PCDEs from <38 to 6800 microgkg-1 d.w., PCDFs from 7.4 to 18000 microgkg-1 d.w. and PCDDs from 9.9 to 35000 microgkg-1 d.w. The resulting WHO-TEQ of PCDD/Fs in the soil samples ranged from 0.14 to 3000 microgkg-1 d.w. Despite a wide range of concentrations the congener compositions were similar within tetrachlorophenate and pentachlorophenate contaminated soils respectively. The contamination at each sawmill site may be linked to the use of either a tetrachlorphenol preservative, e.g. Ky-5, or a pentachlorophenol preservative, e.g. Dowicide G. Best-fit calculations were used to compare the chlorinated phenol contents of the preservatives to those of the soil samples. This revealed a positive correlation between the hydrophobicity (logKow) of contaminants and the ratio of their levels in soil to preservatives. The relative abundance of the chlorinated compounds varied greatly between the five sites studied, suggesting that their transport parameters differ substantially.

Benzofurans↗
PubMed2005

Membrane-assisted solvent extraction of seven phenols combined with large volume injection-gas chromatography-mass spectrometric detection.

Membrane-assisted solvent extraction (MASE) was applied for the determination of seven phenols (phenol, 2-chlorophenol, 2,4-dimethylphenol, 2,4-dichlorophenol, 4-chloro-3-methylphenol, 2,4,6-trichlorophenol and pentachlorophenol) with log Kow (octanol-water-partition-coefficient) between 1.46 (phenol) and 5.12 (pentachlorophenol) in water. The extraction solvents cyclohexane, ethyl acetate and chloroform were tested and ethyl acetate proved to be the best choice. The optimisation of extraction conditions showed the necessity of adding 5 g of sodium chloride to each aqueous sample to give a saturated solution (333 g/L). The pH-value of the sample was adjusted to 2 in order to convert all compounds into their neutral form. An extraction time of 60 min was found to be optimal. Under these conditions the recovery of phenol, the most polar compound, was 11%. The recoveries of the other analytes ranged between 42% (2-chlorophenol) and 98% (2,4-dichlorophenol). Calibration was performed using large volume injection (100 microL injection volume). At optimised conditions the limits of detection were between 0.01 and 0.6 microg/L and the relative standard deviation (n = 3) was on average about 10%. After the method optimisation with reagent water membrane-assisted solvent extraction was applied to two contaminated ground water samples from the region of Bitterfeld in Saxony-Anhalt, Germany. The results demonstrate the good applicability of membrane-assisted solvent extraction for polar analytes like phenols, without the necessity of derivatisation or a difficult and time-consuming sample preparation.

Automation↗