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1

Bockers, Margret, Christiane Rivero, Brigitte Thiede, Thomas Jankowski, and Burkhard Schmidt. "Uptake, Translocation, and Metabolism of 3,4-Dichloroaniline in Soybean and Wheat Plants." Zeitschrift für Naturforschung C 49, no. 11-12 (1994): 719–26. http://dx.doi.org/10.1515/znc-1994-11-1205.

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The roots of 13-day-old soybean ( Glycine max L.) and 7-day-old wheat ( Triticum aestivum L.) hydroponic plants were exposed to [14C]-3,4-dichloroaniline (1.0 and 0.4 mg/1 (6.2 and 2.5 μᴍ) , respectively) and harvested after 48/120 h (soybean) and 72 h (wheat). Both species metabolized the xenobiotic almost quantitatively to N-(β-D-glucopyranosyl)-3,4-dichloroaniline, N-malonyl-3,4-dichloroaniline, 6′-O-malonyl-N-(β-D-glucopyranosyl)-3,4-dichloroaniline and non-extractable residues. In the soybean experiments 58.8 (48 h) and 54.6% (120 h) of the applied radioactivity were found in the nutrient
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2

Gareis, Christine, Christiane Rivero, Ingolf Schuphan, and Burkhard Schmidt. "Plant Metabolism Of Xenobiotics. Comparison Of The Metabolism Of 3.4-Dichloroaniline In Soybean Excised Leaves And Soybean Cell Suspension Cultures." Zeitschrift für Naturforschung C 47, no. 11-12 (1992): 823–29. http://dx.doi.org/10.1515/znc-1992-11-1207.

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Excised leaves and cell suspension cultures of soybean (Glycine max L.) were incubated with [UL-14C]-3,4-dichloroaniline. The compound was almost completely metabolized after 48 h in both systems; it was apparent that the major detoxification pathways present in the excised leaves were also present in the cultured cells. Besides considerable amounts of insoluble residues, the N-glucosyl and the N-malonyl conjugates of 3,4-dichloroaniline, and a yet unknown metabolite was formed in the excised leaves; tentatively the latter was identified with the 6′-O-malonylester of N-glucosyl-3,4-dichloroani
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3

Tatsumi, K., S. Wada, H. Ichikawa, S. Y. Liu, and Jean-Marc Bollag. "Cross-Coupling of a Chloroaniline and Phenolic Acids Catalyzed by a Fungal Enzyme." Water Science and Technology 26, no. 9-11 (1992): 2157–60. http://dx.doi.org/10.2166/wst.1992.0685.

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The reaction between 3,4-dichloroaniline and vanillic, syringic and protocatechuic acids was investigated in the presence of a laccase isolated from the fungus Rhizoctoniapraticola. The aniline alone was not oxidized by the laccase, but if incubated with the phenolic acids and the laccase, cross-linking took place. Particularly the protocatechuic acid and syringic acid reacted with 3,4-dichloroaniline, and cross-linked dimers were isolated as main products.
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4

Sosak-Świderska, Bożena, Danuta Tyrawska, and Barbara Maślikowska. "Microalgal ecotoxicity test with 3,4 - dichloroaniline." Chemosphere 37, no. 14-15 (1998): 2975–82. http://dx.doi.org/10.1016/s0045-6535(98)00338-5.

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5

Ha, Duc Danh. "Investigation of the biodegradation of chloroaniline by Acinetobecter baumannii strain GFJ1." Science and Technology Development Journal 19, no. 4 (2016): 153–59. http://dx.doi.org/10.32508/stdj.v19i4.686.

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Chloroanilines are toxic aromatic compounds which cause environmental pollution, especially water problems, which harmfully affect human and aquatic species. Acinetobecter baumannii strain GFJ1 isolated from soil in Thailand was the first bacterial strain that could utilize several monochloroaniline, dichloroaniline and trichloroanilines as sources of carbon and nitrogen for growth. Among these compounds, GFJ1 degraded 4-chloroaniline and 3,4-chloroaniline with higher rates than others. The analysis of aerobic utilization profile via resting cells showed that the degradation kinetics followed
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6

Song, J., J. Park, H. Chun, S. Yoon, and W. Kim. "3,4-Dichloroaniline induces hepatic steatosis in zebrafish." Toxicology Letters 258 (September 2016): S67. http://dx.doi.org/10.1016/j.toxlet.2016.06.1326.

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7

Yao, Xie-Feng, Fazlurrahman Khan, Rinku Pandey, et al. "Degradation of dichloroaniline isomers by a newly isolated strain, Bacillus megaterium IMT21." Microbiology 157, no. 3 (2011): 721–26. http://dx.doi.org/10.1099/mic.0.045393-0.

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An efficient 3,4-dichloroaniline (3,4-DCA)-mineralizing bacterium has been isolated from enrichment cultures originating from a soil sample with a history of repeated exposure to diuron, a major metabolite of which is 3,4-DCA. This bacterium, Bacillus megaterium IMT21, also mineralized 2,3-, 2,4-, 2,5- and 3,5-DCA as sole sources of carbon and energy. These five DCA isomers were degraded via two different routes. 2,3-, 2,4- and 2,5-DCA were degraded via previously unknown dichloroaminophenol metabolites, whereas 3,4- and 3,5-DCA were degraded via dichloroacetanilide.
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8

Kremer, Stefan, and Olov Sterner. "Metabolism of 3,4-Dichloroaniline by the BasidiomyceteFiloboletusSpecies TA9054." Journal of Agricultural and Food Chemistry 44, no. 4 (1996): 1155–59. http://dx.doi.org/10.1021/jf950539u.

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9

Beyerle‐Pfnür, R., G. Burkhardt, A. Peither, and J. ‐P Lay. "Chronic ecotoxicity of 3,4 dichloroaniline to freshwater ecosystems." Toxicological & Environmental Chemistry 31, no. 1 (1991): 367–73. http://dx.doi.org/10.1080/02772249109357710.

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10

Park, Ji-Seon, Jeongah Song, Jong-Su Park, et al. "3,4-Dichloroaniline promotes fatty liver in zebrafish larvae." Molecular & Cellular Toxicology 16, no. 2 (2020): 159–65. http://dx.doi.org/10.1007/s13273-019-00066-5.

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11

Sasikala, V., D. Sajan, Lynnette Joseph, Badiadka Narayana, and Balladka K. Sarojini. "Spectroscopic and non-linear optical studies of two novel optical limiters from dichloroaniline family crystals: 3,4-Dichloroaniline and 3,5-dichloroaniline." Optics & Laser Technology 96 (November 2017): 23–42. http://dx.doi.org/10.1016/j.optlastec.2017.04.029.

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12

Huang, Deying, Zhengfang Wang, Jianhua Zhang, Jingwei Feng, Zheng Zheng, and Jibiao Zhang. "Gamma radiolytic degradation of 3,4-dichloroaniline in aqueous solution." Separation and Purification Technology 170 (October 2016): 264–71. http://dx.doi.org/10.1016/j.seppur.2016.06.052.

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13

van der Meer, C., C. Teunissen, and Th F. M. Boog. "Toxicity of sodium chromate and 3,4-dichloroaniline to crustaceans." Bulletin of Environmental Contamination and Toxicology 40, no. 2 (1988): 204–11. http://dx.doi.org/10.1007/bf01881040.

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14

Hoeven, Nelly van der. "Effect of 3,4-dichloroaniline and metavanadate on Daphnia populations." Ecotoxicology and Environmental Safety 20, no. 1 (1990): 53–70. http://dx.doi.org/10.1016/0147-6513(90)90046-8.

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15

Schmitz, A., and R. Nagel. "Influence of 3,4-Dichloroaniline (3,4-DCA) on Benthic Invertebrates in Indoor Experimental Streams." Ecotoxicology and Environmental Safety 30, no. 1 (1995): 63–71. http://dx.doi.org/10.1006/eesa.1995.1007.

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16

Ibrahim, Musa Adamu, Syaizwan Zahmir Zulkifli, Mohammad Noor Amal Azmai, Ferdaus Mohamat-Yusuff, and Ahmad Ismail. "Reproductive Toxicity of 3,4-dichloroaniline (3,4-DCA) on Javanese Medaka (Oryziasjavanicus, Bleeker 1854)." Animals 11, no. 3 (2021): 798. http://dx.doi.org/10.3390/ani11030798.

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Compound 3,4-dichloroaniline (3,4-DCA) is a metabolite of several urea herbicides and intermediate chemical of several industrial products. Moreover, 3,4-DCA has been frequently detected in aquatic ecosystems around the world. This aniline is more toxic than the parent chemicals, and it affects non-target organisms. This study evaluated a 21-day reproductive response of an emerging aquatic vertebrate model, Javanese medaka (Oryzias javanicus), exposed to 3,4-DCA. Fecundity and gonads histopathology were observed. The spawning rate and fertilisation reduced significantly in the highest exposed-
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17

Tatsumi, K., S. Y. Liu, and J. M. Bollag. "Enzyme-Catalyzed Complex Formation of Chlorinated Anilines with Humic Substances." Water Science and Technology 25, no. 11 (1992): 57–60. http://dx.doi.org/10.2166/wst.1992.0273.

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The reactions between 4-chloroaniline or 3,4-dichloroaniline and various phenolic humus constituents were investigated in the presence of a laccase isolated from the fungus Rhizoctoniapraticola. The anilines were not oxidized when incubated with laccase; however, if phenolic acids were included in the reaction mixture, cross-linking occurred.
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18

Ibrahim, Musa Adamu, Syaizwan Zahmir Zulkifli, Mohammad Noor Amal Azmai, Ferdaus Mohamat-Yusuff, and Ahmad Ismail. "Embryonic toxicity of 3,4-dichloroaniline (3,4-DCA) on Javanese medaka (Oryzias javanicus Bleeker, 1854)." Toxicology Reports 7 (2020): 1039–45. http://dx.doi.org/10.1016/j.toxrep.2020.08.011.

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19

Donato, A. M., L. Silveira, L. Guilhermino, A. M. V. M. Soares, A. P. Carvalho, and M. C. Lopes. "Toxicity of 3,4-dichloroaniline to male wistar rats blood cells." Pharmacological Research 31 (January 1995): 144. http://dx.doi.org/10.1016/1043-6618(95)86834-8.

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20

Tahir, Muhammad Nawaz, Hazoor Ahmad Shad, Abdul Rauf, and Abdul Haleem Khan. "Crystal structure of 3-{(E)-[(3,4-dichlorophenyl)imino]methyl}benzene-1,2-diol." Acta Crystallographica Section E Crystallographic Communications 71, no. 2 (2015): o137—o138. http://dx.doi.org/10.1107/s2056989015001401.

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In the title Schiff base, C13H9Cl2NO2, which arose from the condensation of 3,4-dichloroaniline with 2,3-dihydroxybenzaldehyde, the dihedral angle between the aromatic rings is 44.74 (13)°. Intramolecular O—H...O and O—H...N hydrogen bonds closeS(5) andS(6) rings, respectively. In the crystal, inversion dimers linked by pairs of O—H...O hydrogen bonds generateR22(10) loops. A weak C—H...π interaction is also observed.
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21

Schiwy, Sabrina, Ann-Kathrin Herber, Henner Hollert, and Markus Brinkmann. "New Insights into the Toxicokinetics of 3,4-Dichloroaniline in Early Life Stages of Zebrafish (Danio rerio)." Toxics 8, no. 1 (2020): 16. http://dx.doi.org/10.3390/toxics8010016.

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In the fish embryo toxicity (FET) test with zebrafish (Danio rerio) embryos, 3,4-dichloroaniline (3,4-DCA) is often employed as a positive control substance. Previous studies have characterized bioconcentration and transformation of 3,4-DCA in this test under flow-through conditions. However, the dynamic changes of chemical concentrations in exposure media and embryos were not studied systematically under the commonly used semi-static exposure conditions in multiwell plates. To overcome these limitations, we conducted semi-static exposures experiments where embryolarval zebrafish were exposed
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22

Carvalho, G., R. Marques, A. R. Lopes, et al. "Biological treatment of propanil and 3,4-dichloroaniline: Kinetic and microbiological characterisation." Water Research 44, no. 17 (2010): 4980–91. http://dx.doi.org/10.1016/j.watres.2010.08.006.

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23

Guilhermino, Lúcia, Amadeu M. V. M. Soares, Arsélio P. Carvalho, and M. Celeste Lopes. "Acute effects of 3,4-dichloroaniline on blood of male wistar rats." Chemosphere 37, no. 4 (1998): 619–32. http://dx.doi.org/10.1016/s0045-6535(98)00087-3.

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24

Sandermann, H., T. J. Musick, and P. W. Aschbacher. "Animal bioavailability of a 3,4-dichloroaniline-lignin metabolite fraction from wheat." Journal of Agricultural and Food Chemistry 40, no. 10 (1992): 2001–7. http://dx.doi.org/10.1021/jf00022a053.

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25

Roehrs, Rafael, Miguel Roehrs, Sérgio L. de O. Machado, and Renato Zanella. "Biodegradation of Herbicide Propanil and Its Subproduct 3,4-Dichloroaniline in Water." CLEAN - Soil, Air, Water 40, no. 9 (2012): 958–64. http://dx.doi.org/10.1002/clen.201100693.

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26

Milan, Marco, Francesco Vidotto, Serenella Piano, Michèle Negre, and Aldo Ferrero. "Dissipation of Propanil and 3,4 Dichloroaniline in Three Different Rice Management Systems." Journal of Environmental Quality 41, no. 5 (2012): 1487–96. http://dx.doi.org/10.2134/jeq2012.0175.

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27

Li, Wei-min, Da-qiang Yin, Yan Zhou, Shuang-qing Hu, and Lian-sheng Wang. "3,4-Dichloroaniline-induced oxidative stress in liver of crucian carp (Carassius auratus)." Ecotoxicology and Environmental Safety 56, no. 2 (2003): 251–55. http://dx.doi.org/10.1016/s0147-6513(02)00117-3.

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28

ZHANG, Bo, and Sen LIN. "Effects of 3,4-Dichloroaniline on Testicle Enzymes as Biological Markers in Rats." Biomedical and Environmental Sciences 22, no. 1 (2009): 40–43. http://dx.doi.org/10.1016/s0895-3988(09)60020-9.

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29

Roehrs, Rafael, Miguel Roehrs, Sérgio L. de O. Machado, and Renato Zanella. "Erratum: Biodegradation of Herbicide Propanil and Its Subproduct 3,4-Dichloroaniline in Water." CLEAN - Soil, Air, Water 40, no. 10 (2012): 1210. http://dx.doi.org/10.1002/clen.201290013.

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30

Rose, Rebecca M., Michael St J. Warne, and Richard P. Lim. "Sensitivity of offspring to chronic 3,4-dichloroaniline exposure varies with maternal exposure." Ecotoxicology and Environmental Safety 58, no. 3 (2004): 405–12. http://dx.doi.org/10.1016/j.ecoenv.2003.09.006.

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31

El-Fantroussi, Said. "Enrichment and Molecular Characterization of a Bacterial Culture That Degrades Methoxy-Methyl Urea Herbicides and Their Aniline Derivatives." Applied and Environmental Microbiology 66, no. 12 (2000): 5110–15. http://dx.doi.org/10.1128/aem.66.12.5110-5115.2000.

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ABSTRACT Soil treated with linuron for more than 10 years showed high biodegradation activity towards methoxy-methyl urea herbicides. Untreated control soil samples taken from the same location did not express any linuron degradation activity, even after 40 days of incubation. Hence, the occurrence in the field of a microbiota having the capacity to degrade a specific herbicide was related to the long-term treatment of the soil. The enrichment culture isolated from treated soil showed specific degradation activity towards methoxy-methyl urea herbicides, such as linuron and metobromuron, while
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32

Premalatha, R., and N. Santhi. "Ultrasonic Assisted Synthesis, Acoustical Property and Antibacterial Activity of some Schiff Bases." International Letters of Chemistry, Physics and Astronomy 33 (May 2014): 53–64. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.33.53.

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An efficient, simple clean synthesis of Schiff bases of some 4-nitroaniline/ 2,4-dinitroaniline/ 3,4-dichloroaniline / 4-methoxy-3-nitro aniline with 3-bromo-4-fluorobenzaldehyde were done by an ultrasound irradiation method. The major advantages of ultra-sonication are short reaction time, operational simplicity, high yield, easy workup and environment friendly procedure. The isolated compounds obtained by ultrasound irradiation method were characterized by UV, IR and NMR spectral data. These acoustical parameters were determined. Furthermore their antibacterial activities are screened agains
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33

Cocaign, Angélique, Linh-Chi Bui, Philippe Silar, et al. "Biotransformation of Trichoderma spp. and Their Tolerance to Aromatic Amines, a Major Class of Pollutants." Applied and Environmental Microbiology 79, no. 15 (2013): 4719–26. http://dx.doi.org/10.1128/aem.00989-13.

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ABSTRACTTrichodermaspp. are cosmopolitan soil fungi that are highly resistant to many toxic compounds. Here, we show thatTrichoderma virensandT. reeseiare tolerant to aromatic amines (AA), a major class of pollutants including the highly toxic pesticide residue 3,4-dichloroaniline (3,4-DCA). In a previous study, we provided proof-of-concept remediation experiments in which another soil fungus,Podospora anserina, detoxifies 3,4-DCA through its arylamineN-acetyltransferase (NAT), a xenobiotic-metabolizing enzyme that enables acetyl coenzyme A-dependent detoxification of AA. To assess whether the
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34

SHAN, Guoqiang, Mengqi YU, Shengsong YU, and Lingyan ZHU. "Analysis of perfluorooctanoic acid by high performance liquid chromatography with 3,4-dichloroaniline derivatization." Chinese Journal of Chromatography 32, no. 9 (2014): 942. http://dx.doi.org/10.3724/sp.j.1123.2014.05028.

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35

Feng, Jingwei, Runlong Liu, Pei Chen, et al. "Degradation of aqueous 3,4-dichloroaniline by a novel dielectric barrier discharge plasma reactor." Environmental Science and Pollution Research 22, no. 6 (2014): 4447–59. http://dx.doi.org/10.1007/s11356-014-3690-1.

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36

Marques, Ricardo, Adrian Oehmen, Gilda Carvalho, and Maria A. M. Reis. "Modelling the biodegradation kinetics of the herbicide propanil and its metabolite 3,4-dichloroaniline." Environmental Science and Pollution Research 22, no. 9 (2014): 6687–95. http://dx.doi.org/10.1007/s11356-014-3870-z.

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37

Lao, Si-Houy, Caroline Loutre, Melissa Brazier, et al. "3,4-Dichloroaniline is detoxified and exported via different pathways in Arabidopsis and soybean." Phytochemistry 63, no. 6 (2003): 653–61. http://dx.doi.org/10.1016/s0031-9422(03)00289-9.

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38

Girling, A. E., L. Tattersfield, G. C. Mitchell, et al. "Derivation of Predicted No-Effect Concentrations for Lindane, 3,4-Dichloroaniline, Atrazine, and Copper." Ecotoxicology and Environmental Safety 46, no. 2 (2000): 148–62. http://dx.doi.org/10.1006/eesa.1999.1901.

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39

Zhu, Bin, Tianqiang Liu, Xuegang Hu, and Gaoxue Wang. "Developmental toxicity of 3,4-dichloroaniline on rare minnow (Gobiocypris rarus) embryos and larvae." Chemosphere 90, no. 3 (2013): 1132–39. http://dx.doi.org/10.1016/j.chemosphere.2012.09.021.

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40

Crossland, N. O. "A review of the fate and toxicity of 3,4-dichloroaniline in aquatic environments." Chemosphere 21, no. 12 (1990): 1489–97. http://dx.doi.org/10.1016/0045-6535(90)90054-w.

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41

Bauchinger, M., U. Kulka, and E. Schmid. "Cytogenetic effects of 3,4-dichloroaniline in human lymphocytes and V79 Chinese hamster cells." Mutation Research Letters 226, no. 3 (1989): 197–202. http://dx.doi.org/10.1016/0165-7992(89)90020-1.

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42

Willberg, D. M., P. S. Lang, R. H. Höchemer, A. Kratel, and M. R. Hoffmann. "Degradation of 4-Chlorophenol, 3,4-Dichloroaniline, and 2,4,6-Trinitrotoluene in an Electrohydraulic Discharge Reactor." Environmental Science & Technology 30, no. 8 (1996): 2526–34. http://dx.doi.org/10.1021/es950850s.

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43

Schäfers, Christoph, and Roland Nagel. "Consequences of 3,4-dichloroaniline to guppy populations (Poecilia reticulata): computer simulation and experimental validation." Science of The Total Environment 134 (January 1993): 1471–78. http://dx.doi.org/10.1016/s0048-9697(05)80152-4.

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44

Goewie, Chérie E., and Elbert A. Hogendoorn. "Liquid chromatographic determination of the herbicide diuron and its metabolite 3,4‐dichloroaniline in asparagus." Food Additives & Contaminants 2, no. 3 (1985): 217–20. http://dx.doi.org/10.1080/02652038509373546.

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45

PASTORELLI, ROBERTA, GIOVANNI CATENACCI, MARCO GUANCI, et al. "3,4 Dichloroaniline-haemoglobin adducts in humans: preliminary data on agricultural workers exposed to propanil." Biomarkers 3, no. 3 (1998): 227–33. http://dx.doi.org/10.1080/135475098231246.

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46

Pieper, Dietmar Helmut, Reinhard Winkler, and Heinrich Sandermann. "Formation of a Toxic Dimerization Product of 3,4-Dichloroaniline by Lignin Peroxidase fromPhanerochaete chrysosporium." Angewandte Chemie International Edition in English 31, no. 1 (1992): 68–70. http://dx.doi.org/10.1002/anie.199200681.

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47

Hertl, Johannes, and Roland Nagel. "Bioconcentration and metabolism of 3,4-dichloroaniline in different life stages of guppy and zebrafish." Chemosphere 27, no. 11 (1993): 2225–34. http://dx.doi.org/10.1016/0045-6535(93)90134-q.

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48

Ensenbachl, Uwe, Renate Hryk, and Roland Nagel. "Kinetics of 3,4-dichloroaniline in several fish species exposed to different types of water." Chemosphere 32, no. 8 (1996): 1643–54. http://dx.doi.org/10.1016/0045-6535(96)00074-4.

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49

Elendt, B. P. "Influence of water composition on the chronic toxicity of 3,4-dichloroaniline to Daphnia magna." Water Research 24, no. 9 (1990): 1169–72. http://dx.doi.org/10.1016/0043-1354(90)90181-5.

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50

Morgado, J. M., and A. M. V. M. Soares. "Activity of pyruvate kinase and malate dehydrogenase in Daphnia magna under 3,4-dichloroaniline stress." Archives of Environmental Contamination and Toxicology 29, no. 1 (1995): 94–96. http://dx.doi.org/10.1007/bf00213092.

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