Parameters Influencing Biotransformation Rates of Phenylurea Herbicides by Soil Microorganisms
The biotransformation of phenylurea herbicides and some of their most prominent degradates by different soil microorganisms was investigated. Most soil fungi, but only some soil bacteria, were able to reduce the herbicide concentration in the culture medium. Biotransformation rates of the compounds...
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Veröffentlicht in: | Pesticide biochemistry and physiology 1998-07, Vol.60 (2), p.71-82 |
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description | The biotransformation of phenylurea herbicides and some of their most prominent degradates by different soil microorganisms was investigated. Most soil fungi, but only some soil bacteria, were able to reduce the herbicide concentration in the culture medium. Biotransformation rates of the compounds were different. Identification of the products demonstrated that N-demethylation was the most common initial biotransformation step. Cleavage of the urea bridge was only observed by bacteria. Sorption of the compounds to the mycelium or cells was different among the microorganisms investigated, but studies with14C-labeled compounds revealed that the herbicides were not bound to any organic material such as cell walls or membranes. Mineralization of the phenyl ring did not occur. None of the microorganisms were able to use the herbicides as the sole carbon source, indicating that biotransformation was a cometabolic process. In some cases, the different biotransformation rates correlated with the lipophilicity of the compounds. Herbicides with high octanol-water partition coefficients were then transformed faster than compounds with a high water solubility. Some microorganisms, however, showed rapid biotransformation of certain, but different, herbicides. This indicates either additional biotransformation pathways or substrate specificities. |
doi_str_mv | 10.1006/pest.1998.2324 |
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Most soil fungi, but only some soil bacteria, were able to reduce the herbicide concentration in the culture medium. Biotransformation rates of the compounds were different. Identification of the products demonstrated that N-demethylation was the most common initial biotransformation step. Cleavage of the urea bridge was only observed by bacteria. Sorption of the compounds to the mycelium or cells was different among the microorganisms investigated, but studies with14C-labeled compounds revealed that the herbicides were not bound to any organic material such as cell walls or membranes. Mineralization of the phenyl ring did not occur. None of the microorganisms were able to use the herbicides as the sole carbon source, indicating that biotransformation was a cometabolic process. In some cases, the different biotransformation rates correlated with the lipophilicity of the compounds. Herbicides with high octanol-water partition coefficients were then transformed faster than compounds with a high water solubility. Some microorganisms, however, showed rapid biotransformation of certain, but different, herbicides. This indicates either additional biotransformation pathways or substrate specificities.</description><identifier>ISSN: 0048-3575</identifier><identifier>EISSN: 1095-9939</identifier><identifier>DOI: 10.1006/pest.1998.2324</identifier><identifier>CODEN: PCBPBS</identifier><language>eng</language><publisher>San Diego, CA: Elsevier Inc</publisher><subject>Agronomy. Soil science and plant productions ; Animal, plant and microbial ecology ; Applied ecology ; BACTERIA ; BIOCHEMICAL PATHWAYS ; BIODEGRADACION ; BIODEGRADATION ; Biological and medical sciences ; biotransformation ; CHAMPIGNON DU SOL ; Chemical control ; Ecotoxicology, biological effects of pollution ; FLORA DEL SUELO ; FLORE DU SOL ; Fundamental and applied biological sciences. Psychology ; General agronomy. Plant production ; HERBICIDAS ; HERBICIDE ; HERBICIDES ; HONGOS DEL SUELO ; LIPOPHILICITY ; METABOLISM ; METABOLISME ; METABOLISMO ; MICROBIAL DEGRADATION ; microorganisms ; OCTANOL-WATER PARTITION COEFFICIENTS ; Parasitic plants. Weeds ; phenylurea ; phenylureas ; Phytopathology. Animal pests. Plant and forest protection ; SOIL FLORA ; SOIL FUNGI ; STRUCTURE ACTIVITY RELATIONSHIPS ; structure-reactivity relationships ; Terrestrial environment, soil, air ; Use of agricultural and forest wastes. Biomass use, bioconversion ; VIA BIOQUIMICA DEL METABOLISMO ; VOIE BIOCHIMIQUE DU METABOLISME ; Weeds</subject><ispartof>Pesticide biochemistry and physiology, 1998-07, Vol.60 (2), p.71-82</ispartof><rights>1998 Academic Press</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-dadfecfba81104ea16716820db33cf0bb74bc372ceb1fff9c2acf78cfeec78f73</citedby><cites>FETCH-LOGICAL-c368t-dadfecfba81104ea16716820db33cf0bb74bc372ceb1fff9c2acf78cfeec78f73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0048357598923240$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2434476$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Berger, Bernhard M.</creatorcontrib><title>Parameters Influencing Biotransformation Rates of Phenylurea Herbicides by Soil Microorganisms</title><title>Pesticide biochemistry and physiology</title><description>The biotransformation of phenylurea herbicides and some of their most prominent degradates by different soil microorganisms was investigated. Most soil fungi, but only some soil bacteria, were able to reduce the herbicide concentration in the culture medium. Biotransformation rates of the compounds were different. Identification of the products demonstrated that N-demethylation was the most common initial biotransformation step. Cleavage of the urea bridge was only observed by bacteria. Sorption of the compounds to the mycelium or cells was different among the microorganisms investigated, but studies with14C-labeled compounds revealed that the herbicides were not bound to any organic material such as cell walls or membranes. Mineralization of the phenyl ring did not occur. None of the microorganisms were able to use the herbicides as the sole carbon source, indicating that biotransformation was a cometabolic process. In some cases, the different biotransformation rates correlated with the lipophilicity of the compounds. Herbicides with high octanol-water partition coefficients were then transformed faster than compounds with a high water solubility. Some microorganisms, however, showed rapid biotransformation of certain, but different, herbicides. This indicates either additional biotransformation pathways or substrate specificities.</description><subject>Agronomy. Soil science and plant productions</subject><subject>Animal, plant and microbial ecology</subject><subject>Applied ecology</subject><subject>BACTERIA</subject><subject>BIOCHEMICAL PATHWAYS</subject><subject>BIODEGRADACION</subject><subject>BIODEGRADATION</subject><subject>Biological and medical sciences</subject><subject>biotransformation</subject><subject>CHAMPIGNON DU SOL</subject><subject>Chemical control</subject><subject>Ecotoxicology, biological effects of pollution</subject><subject>FLORA DEL SUELO</subject><subject>FLORE DU SOL</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General agronomy. Plant production</subject><subject>HERBICIDAS</subject><subject>HERBICIDE</subject><subject>HERBICIDES</subject><subject>HONGOS DEL SUELO</subject><subject>LIPOPHILICITY</subject><subject>METABOLISM</subject><subject>METABOLISME</subject><subject>METABOLISMO</subject><subject>MICROBIAL DEGRADATION</subject><subject>microorganisms</subject><subject>OCTANOL-WATER PARTITION COEFFICIENTS</subject><subject>Parasitic plants. Weeds</subject><subject>phenylurea</subject><subject>phenylureas</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>SOIL FLORA</subject><subject>SOIL FUNGI</subject><subject>STRUCTURE ACTIVITY RELATIONSHIPS</subject><subject>structure-reactivity relationships</subject><subject>Terrestrial environment, soil, air</subject><subject>Use of agricultural and forest wastes. Biomass use, bioconversion</subject><subject>VIA BIOQUIMICA DEL METABOLISMO</subject><subject>VOIE BIOCHIMIQUE DU METABOLISME</subject><subject>Weeds</subject><issn>0048-3575</issn><issn>1095-9939</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><recordid>eNp1kM9P3DAQha0KpC4_rr1VygH1lsWOs7F9pIgCEghUyhVrMhkvRkm8tbOV9r_H0aLeOM3hfe9p9DH2TfCl4Lw531CalsIYvaxkVX9hC8HNqjRGmgO24LzWpVyp1Vd2lNIb59zU3CzYyyNEGGiimIrb0fVbGtGP6-KnD1OEMbkQB5h8GIvfMFEqgiseX2nc9dtIUNxQbD36LgftrngKvi_uPcYQ4hpGn4Z0wg4d9IlOP-4xe_519efyprx7uL69vLgrUTZ6KjvoHKFrQQvBawLRKNHoinetlOh426q6RakqpFY45wxWgE5pdESotFPymP3Y725i-LvNIuzgE1Lfw0hhm6xQK10JMYPLPZi_TCmSs5voB4g7K7idNdpZo5012lljLpx9LENC6F2Wgj79b2WirlWTse97zEGwsI4ZeX7KK4ZzYYTMud7nlC388xRtQp9dU-cj4WS74D_74B33SJKy</recordid><startdate>19980701</startdate><enddate>19980701</enddate><creator>Berger, Bernhard M.</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>19980701</creationdate><title>Parameters Influencing Biotransformation Rates of Phenylurea Herbicides by Soil Microorganisms</title><author>Berger, Bernhard M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-dadfecfba81104ea16716820db33cf0bb74bc372ceb1fff9c2acf78cfeec78f73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Animal, plant and microbial ecology</topic><topic>Applied ecology</topic><topic>BACTERIA</topic><topic>BIOCHEMICAL PATHWAYS</topic><topic>BIODEGRADACION</topic><topic>BIODEGRADATION</topic><topic>Biological and medical sciences</topic><topic>biotransformation</topic><topic>CHAMPIGNON DU SOL</topic><topic>Chemical control</topic><topic>Ecotoxicology, biological effects of pollution</topic><topic>FLORA DEL SUELO</topic><topic>FLORE DU SOL</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General agronomy. Plant production</topic><topic>HERBICIDAS</topic><topic>HERBICIDE</topic><topic>HERBICIDES</topic><topic>HONGOS DEL SUELO</topic><topic>LIPOPHILICITY</topic><topic>METABOLISM</topic><topic>METABOLISME</topic><topic>METABOLISMO</topic><topic>MICROBIAL DEGRADATION</topic><topic>microorganisms</topic><topic>OCTANOL-WATER PARTITION COEFFICIENTS</topic><topic>Parasitic plants. Weeds</topic><topic>phenylurea</topic><topic>phenylureas</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>SOIL FLORA</topic><topic>SOIL FUNGI</topic><topic>STRUCTURE ACTIVITY RELATIONSHIPS</topic><topic>structure-reactivity relationships</topic><topic>Terrestrial environment, soil, air</topic><topic>Use of agricultural and forest wastes. Biomass use, bioconversion</topic><topic>VIA BIOQUIMICA DEL METABOLISMO</topic><topic>VOIE BIOCHIMIQUE DU METABOLISME</topic><topic>Weeds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Berger, Bernhard M.</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Pesticide biochemistry and physiology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Berger, Bernhard M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Parameters Influencing Biotransformation Rates of Phenylurea Herbicides by Soil Microorganisms</atitle><jtitle>Pesticide biochemistry and physiology</jtitle><date>1998-07-01</date><risdate>1998</risdate><volume>60</volume><issue>2</issue><spage>71</spage><epage>82</epage><pages>71-82</pages><issn>0048-3575</issn><eissn>1095-9939</eissn><coden>PCBPBS</coden><abstract>The biotransformation of phenylurea herbicides and some of their most prominent degradates by different soil microorganisms was investigated. Most soil fungi, but only some soil bacteria, were able to reduce the herbicide concentration in the culture medium. Biotransformation rates of the compounds were different. Identification of the products demonstrated that N-demethylation was the most common initial biotransformation step. Cleavage of the urea bridge was only observed by bacteria. Sorption of the compounds to the mycelium or cells was different among the microorganisms investigated, but studies with14C-labeled compounds revealed that the herbicides were not bound to any organic material such as cell walls or membranes. Mineralization of the phenyl ring did not occur. None of the microorganisms were able to use the herbicides as the sole carbon source, indicating that biotransformation was a cometabolic process. In some cases, the different biotransformation rates correlated with the lipophilicity of the compounds. 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subjects | Agronomy. Soil science and plant productions Animal, plant and microbial ecology Applied ecology BACTERIA BIOCHEMICAL PATHWAYS BIODEGRADACION BIODEGRADATION Biological and medical sciences biotransformation CHAMPIGNON DU SOL Chemical control Ecotoxicology, biological effects of pollution FLORA DEL SUELO FLORE DU SOL Fundamental and applied biological sciences. Psychology General agronomy. Plant production HERBICIDAS HERBICIDE HERBICIDES HONGOS DEL SUELO LIPOPHILICITY METABOLISM METABOLISME METABOLISMO MICROBIAL DEGRADATION microorganisms OCTANOL-WATER PARTITION COEFFICIENTS Parasitic plants. Weeds phenylurea phenylureas Phytopathology. Animal pests. Plant and forest protection SOIL FLORA SOIL FUNGI STRUCTURE ACTIVITY RELATIONSHIPS structure-reactivity relationships Terrestrial environment, soil, air Use of agricultural and forest wastes. Biomass use, bioconversion VIA BIOQUIMICA DEL METABOLISMO VOIE BIOCHIMIQUE DU METABOLISME Weeds |
title | Parameters Influencing Biotransformation Rates of Phenylurea Herbicides by Soil Microorganisms |
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