Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors
Protox inhibitors are applied as foliar sprays, thus causing very rapid cellular collapse and desiccation of many troublesome weeds in the presence of light. In many respects, they appear to be ideal herbicides, because they act rapidly and do not harm mammals under normal conditions. The main limit...
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| Veröffentlicht in: | Pest management science 2004-12, Vol.60 (12), p.1178-1188 |
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| creator | Meazza, Giovanni Bettarini, Franco Porta, Piero La Piccardi, Paolo Signorini, Ernesto Portoso, Domenico Fornara, Luca |
| description | Protox inhibitors are applied as foliar sprays, thus causing very rapid cellular collapse and desiccation of many troublesome weeds in the presence of light. In many respects, they appear to be ideal herbicides, because they act rapidly and do not harm mammals under normal conditions. The main limitation to their widespread adoption is that few crops are naturally resistant to them. Crop tolerance has mainly been pursued with the synthesis of the cyclic imide classes containing 5‐ and 6‐membered heterocycles, including pyrazole, pyridazine, 1,2,4‐triazine, triazolinone and trifluoromethyluracil derivatives. Because of their structural novelties and biological performance, active investigations on heterocyclic protox inhibitors have been carried out in our laboratories and we have found 3‐arylpyrroles to be a new class of light‐activated, membrane‐disrupting herbicides. They are active on both grass and broadleaf weeds at low rates. The synthesis and structure–activity relationships are presented. Copyright © 2004 Society of Chemical Industry |
| doi_str_mv | 10.1002/ps.923 |
| format | Article |
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In many respects, they appear to be ideal herbicides, because they act rapidly and do not harm mammals under normal conditions. The main limitation to their widespread adoption is that few crops are naturally resistant to them. Crop tolerance has mainly been pursued with the synthesis of the cyclic imide classes containing 5‐ and 6‐membered heterocycles, including pyrazole, pyridazine, 1,2,4‐triazine, triazolinone and trifluoromethyluracil derivatives. Because of their structural novelties and biological performance, active investigations on heterocyclic protox inhibitors have been carried out in our laboratories and we have found 3‐arylpyrroles to be a new class of light‐activated, membrane‐disrupting herbicides. They are active on both grass and broadleaf weeds at low rates. The synthesis and structure–activity relationships are presented. Copyright © 2004 Society of Chemical Industry</description><identifier>ISSN: 1526-498X</identifier><identifier>EISSN: 1526-4998</identifier><identifier>DOI: 10.1002/ps.923</identifier><identifier>PMID: 15578598</identifier><identifier>CODEN: PMSCFC</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>arylpyrroles ; Biological and medical sciences ; Chemical control ; Crops ; Enzymes ; Fundamental and applied biological sciences. Psychology ; Galium aparine ; herbicide ; Herbicides ; Herbicides - chemical synthesis ; Herbicides - pharmacology ; Molecular Structure ; Oxidoreductases Acting on CH-CH Group Donors - antagonists & inhibitors ; Parasitic plants. Weeds ; Phytopathology. Animal pests. Plant and forest protection ; Plants, Edible ; Protoporphyrinogen Oxidase ; protox inhibitor ; Pyrroles - chemical synthesis ; Pyrroles - pharmacology ; Weeds</subject><ispartof>Pest management science, 2004-12, Vol.60 (12), p.1178-1188</ispartof><rights>2004 Society of Chemical Industry</rights><rights>2005 INIST-CNRS</rights><rights>2004 Society of Chemical Industry.</rights><rights>Copyright John Wiley and Sons, Limited Dec 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4703-a01abe8237c83974e340401211d11756c0b00b20fedaa6499d6b5b9f6bc5662b3</citedby><cites>FETCH-LOGICAL-c4703-a01abe8237c83974e340401211d11756c0b00b20fedaa6499d6b5b9f6bc5662b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fps.923$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fps.923$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16302152$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15578598$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Meazza, Giovanni</creatorcontrib><creatorcontrib>Bettarini, Franco</creatorcontrib><creatorcontrib>Porta, Piero La</creatorcontrib><creatorcontrib>Piccardi, Paolo</creatorcontrib><creatorcontrib>Signorini, Ernesto</creatorcontrib><creatorcontrib>Portoso, Domenico</creatorcontrib><creatorcontrib>Fornara, Luca</creatorcontrib><title>Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors</title><title>Pest management science</title><addtitle>Pest. Manag. Sci</addtitle><description>Protox inhibitors are applied as foliar sprays, thus causing very rapid cellular collapse and desiccation of many troublesome weeds in the presence of light. In many respects, they appear to be ideal herbicides, because they act rapidly and do not harm mammals under normal conditions. The main limitation to their widespread adoption is that few crops are naturally resistant to them. Crop tolerance has mainly been pursued with the synthesis of the cyclic imide classes containing 5‐ and 6‐membered heterocycles, including pyrazole, pyridazine, 1,2,4‐triazine, triazolinone and trifluoromethyluracil derivatives. Because of their structural novelties and biological performance, active investigations on heterocyclic protox inhibitors have been carried out in our laboratories and we have found 3‐arylpyrroles to be a new class of light‐activated, membrane‐disrupting herbicides. They are active on both grass and broadleaf weeds at low rates. The synthesis and structure–activity relationships are presented. Copyright © 2004 Society of Chemical Industry</description><subject>arylpyrroles</subject><subject>Biological and medical sciences</subject><subject>Chemical control</subject><subject>Crops</subject><subject>Enzymes</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Galium aparine</subject><subject>herbicide</subject><subject>Herbicides</subject><subject>Herbicides - chemical synthesis</subject><subject>Herbicides - pharmacology</subject><subject>Molecular Structure</subject><subject>Oxidoreductases Acting on CH-CH Group Donors - antagonists & inhibitors</subject><subject>Parasitic plants. Weeds</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Plants, Edible</subject><subject>Protoporphyrinogen Oxidase</subject><subject>protox inhibitor</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - pharmacology</subject><subject>Weeds</subject><issn>1526-498X</issn><issn>1526-4998</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp10Mtu3CAUBmBUJWruj1BZlRqpCycHMNgso1GbiTRJK-XSbiIEGHdIHeOCZxq_fYg8SlZZgcTH-eFH6AjDCQYgp308EYR-QLuYEZ4XQlRbr_vq9w7ai_EBAIQQ5CPawYyVFRPVLrq_HrthaaOLmerqbGmDdsbVqs2UGdzaDWPmm6zza9umw8EGb0bTOpP1wQ--96FfjsF1_o_tMv-ULkabuW7ptBt8iAdou1FttIebdR_dfv92M5vnix_nF7OzRW6KEmiuACttK0JLU1FRFpYWUAAmGNcYl4wb0ACaQGNrpXj6XM0106Lh2jDOiab76PM0N73q38rGQT74VehSpCSEsIpgThI6npAJPsZgG9kH96jCKDHIlxJlH2UqMcFPm2kr_WjrN7ZpLYEvG6CiUW0TVGdcfHOcAkndJ_d1cv9da8d34uTP6yk0n6yLg316tSr8lbykJZO_rs4lZRgWl7M7OafPP8GWmg</recordid><startdate>200412</startdate><enddate>200412</enddate><creator>Meazza, Giovanni</creator><creator>Bettarini, Franco</creator><creator>Porta, Piero La</creator><creator>Piccardi, Paolo</creator><creator>Signorini, Ernesto</creator><creator>Portoso, Domenico</creator><creator>Fornara, Luca</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QR</scope><scope>7SS</scope><scope>7ST</scope><scope>7T7</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>SOI</scope></search><sort><creationdate>200412</creationdate><title>Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors</title><author>Meazza, Giovanni ; Bettarini, Franco ; Porta, Piero La ; Piccardi, Paolo ; Signorini, Ernesto ; Portoso, Domenico ; Fornara, Luca</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4703-a01abe8237c83974e340401211d11756c0b00b20fedaa6499d6b5b9f6bc5662b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>arylpyrroles</topic><topic>Biological and medical sciences</topic><topic>Chemical control</topic><topic>Crops</topic><topic>Enzymes</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Galium aparine</topic><topic>herbicide</topic><topic>Herbicides</topic><topic>Herbicides - chemical synthesis</topic><topic>Herbicides - pharmacology</topic><topic>Molecular Structure</topic><topic>Oxidoreductases Acting on CH-CH Group Donors - antagonists & inhibitors</topic><topic>Parasitic plants. Weeds</topic><topic>Phytopathology. Animal pests. 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| subjects | arylpyrroles Biological and medical sciences Chemical control Crops Enzymes Fundamental and applied biological sciences. Psychology Galium aparine herbicide Herbicides Herbicides - chemical synthesis Herbicides - pharmacology Molecular Structure Oxidoreductases Acting on CH-CH Group Donors - antagonists & inhibitors Parasitic plants. Weeds Phytopathology. Animal pests. Plant and forest protection Plants, Edible Protoporphyrinogen Oxidase protox inhibitor Pyrroles - chemical synthesis Pyrroles - pharmacology Weeds |
| title | Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors |
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