Differential Routes of Metabolism of Imidazolinones: Basis for Soybean ( Glycine max) Selectivity
Imazaquin and imazethapyr are soybean-selective herbicides. The major factor for the selectivity of these imidazolinone herbicides is the ability of soybeans to rapidly metabolize the herbicides to inactive compounds. Metabolites of these herbicides were isolated and characterized by synthesis and m...
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| Veröffentlicht in: | Pesticide biochemistry and physiology 1993-06, Vol.46 (2), p.120-130 |
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| container_title | Pesticide biochemistry and physiology |
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| creator | Tecle, B. Dacunha, A. Shaner, D.L. |
| description | Imazaquin and imazethapyr are soybean-selective herbicides. The major factor for the selectivity of these imidazolinone herbicides is the ability of soybeans to rapidly metabolize the herbicides to inactive compounds. Metabolites of these herbicides were isolated and characterized by synthesis and mass spectrometry. The metabolic pathway of imazaquin involved the cyclization of the imidazolinyl nitrogen and the carboxyl group followed by rapid degradation to one major and three minor metabolites. Imazethapyr, on the other hand, is hydroxylated at the 5-ethyl substituent of the pyridine ring followed by O-glucosylation. The differential routes of metabolism of these two imidazolinone herbicides in soybean are typical examples of oxidation, ring cleavage, and conjugation metabolic reactions in the herbicide detoxification mechanisms. |
| doi_str_mv | 10.1006/pest.1993.1043 |
| format | Article |
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The major factor for the selectivity of these imidazolinone herbicides is the ability of soybeans to rapidly metabolize the herbicides to inactive compounds. Metabolites of these herbicides were isolated and characterized by synthesis and mass spectrometry. The metabolic pathway of imazaquin involved the cyclization of the imidazolinyl nitrogen and the carboxyl group followed by rapid degradation to one major and three minor metabolites. Imazethapyr, on the other hand, is hydroxylated at the 5-ethyl substituent of the pyridine ring followed by O-glucosylation. The differential routes of metabolism of these two imidazolinone herbicides in soybean are typical examples of oxidation, ring cleavage, and conjugation metabolic reactions in the herbicide detoxification mechanisms.</description><identifier>ISSN: 0048-3575</identifier><identifier>EISSN: 1095-9939</identifier><identifier>DOI: 10.1006/pest.1993.1043</identifier><identifier>CODEN: PCBPBS</identifier><language>eng</language><publisher>San Diego, CA: Elsevier Inc</publisher><subject>Agronomy. Soil science and plant productions ; Biological and medical sciences ; Chemical control ; DESINTOXICACION ; DETOXIFICATION ; Fundamental and applied biological sciences. Psychology ; GLYCINE MAX ; HERBICIDAS ; HERBICIDE ; METABOLISME ; METABOLISMO ; METABOLITE ; METABOLITOS ; Parasitic plants. Weeds ; Phytopathology. Animal pests. 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The major factor for the selectivity of these imidazolinone herbicides is the ability of soybeans to rapidly metabolize the herbicides to inactive compounds. Metabolites of these herbicides were isolated and characterized by synthesis and mass spectrometry. The metabolic pathway of imazaquin involved the cyclization of the imidazolinyl nitrogen and the carboxyl group followed by rapid degradation to one major and three minor metabolites. Imazethapyr, on the other hand, is hydroxylated at the 5-ethyl substituent of the pyridine ring followed by O-glucosylation. The differential routes of metabolism of these two imidazolinone herbicides in soybean are typical examples of oxidation, ring cleavage, and conjugation metabolic reactions in the herbicide detoxification mechanisms.</description><subject>Agronomy. Soil science and plant productions</subject><subject>Biological and medical sciences</subject><subject>Chemical control</subject><subject>DESINTOXICACION</subject><subject>DETOXIFICATION</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>GLYCINE MAX</subject><subject>HERBICIDAS</subject><subject>HERBICIDE</subject><subject>METABOLISME</subject><subject>METABOLISMO</subject><subject>METABOLITE</subject><subject>METABOLITOS</subject><subject>Parasitic plants. Weeds</subject><subject>Phytopathology. Animal pests. Plant and forest protection</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>1993</creationdate><recordtype>article</recordtype><recordid>eNp1kL1PwzAQxS0EEqWwMjB5YIAhxa6T2maD8lWpCInS2bo4Z2SUxpUdKspfT6IiNqbT03vvTvcj5JSzEWdscrXG1I641qKTudgjA850kXVa75MBY7nKRCGLQ3KU0gdjTOdMDwjceecwYtN6qOlr-Gwx0eDoM7ZQhtqnVa9mK1_Bdyeb0GC6preQfKIuRLoI2xKhoRf0sd5a3yBdwdclXWCNtvUb326PyYGDOuHJ7xyS5cP92_Qpm788zqY388wKkbfZBFwJlZVQyolwjI1VpZRwsqoYV1ZplQuuBY5FWUgHVqpxibnDUqMsOKuUGJLRbq-NIaWIzqyjX0HcGs5MD8j0gEwPyPSAusL5rrCGZKF2ERrr018rl1op3cfOdjEHwcB77CLLhc65LiTvTLUzsfts4zGaZD02FisfOwCmCv6_8z9LS4LW</recordid><startdate>19930601</startdate><enddate>19930601</enddate><creator>Tecle, B.</creator><creator>Dacunha, A.</creator><creator>Shaner, D.L.</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19930601</creationdate><title>Differential Routes of Metabolism of Imidazolinones: Basis for Soybean ( Glycine max) Selectivity</title><author>Tecle, B. ; Dacunha, A. ; Shaner, D.L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c334t-6afbadc7ab763f0028d883f7dd018c89843193e23b57fac782be4feb9e7510d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Biological and medical sciences</topic><topic>Chemical control</topic><topic>DESINTOXICACION</topic><topic>DETOXIFICATION</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>GLYCINE MAX</topic><topic>HERBICIDAS</topic><topic>HERBICIDE</topic><topic>METABOLISME</topic><topic>METABOLISMO</topic><topic>METABOLITE</topic><topic>METABOLITOS</topic><topic>Parasitic plants. Weeds</topic><topic>Phytopathology. Animal pests. Plant and forest protection</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>Tecle, B.</creatorcontrib><creatorcontrib>Dacunha, A.</creatorcontrib><creatorcontrib>Shaner, D.L.</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Pesticide biochemistry and physiology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tecle, B.</au><au>Dacunha, A.</au><au>Shaner, D.L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Differential Routes of Metabolism of Imidazolinones: Basis for Soybean ( Glycine max) Selectivity</atitle><jtitle>Pesticide biochemistry and physiology</jtitle><date>1993-06-01</date><risdate>1993</risdate><volume>46</volume><issue>2</issue><spage>120</spage><epage>130</epage><pages>120-130</pages><issn>0048-3575</issn><eissn>1095-9939</eissn><coden>PCBPBS</coden><abstract>Imazaquin and imazethapyr are soybean-selective herbicides. The major factor for the selectivity of these imidazolinone herbicides is the ability of soybeans to rapidly metabolize the herbicides to inactive compounds. Metabolites of these herbicides were isolated and characterized by synthesis and mass spectrometry. The metabolic pathway of imazaquin involved the cyclization of the imidazolinyl nitrogen and the carboxyl group followed by rapid degradation to one major and three minor metabolites. Imazethapyr, on the other hand, is hydroxylated at the 5-ethyl substituent of the pyridine ring followed by O-glucosylation. The differential routes of metabolism of these two imidazolinone herbicides in soybean are typical examples of oxidation, ring cleavage, and conjugation metabolic reactions in the herbicide detoxification mechanisms.</abstract><cop>San Diego, CA</cop><pub>Elsevier Inc</pub><doi>10.1006/pest.1993.1043</doi><tpages>11</tpages></addata></record> |
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| ispartof | Pesticide biochemistry and physiology, 1993-06, Vol.46 (2), p.120-130 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Agronomy. Soil science and plant productions Biological and medical sciences Chemical control DESINTOXICACION DETOXIFICATION Fundamental and applied biological sciences. Psychology GLYCINE MAX HERBICIDAS HERBICIDE METABOLISME METABOLISMO METABOLITE METABOLITOS Parasitic plants. Weeds Phytopathology. Animal pests. Plant and forest protection VIA BIOQUIMICA DEL METABOLISMO VOIE BIOCHIMIQUE DU METABOLISME Weeds |
| title | Differential Routes of Metabolism of Imidazolinones: Basis for Soybean ( Glycine max) Selectivity |
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