<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>0871-018X</journal-id>
<journal-title><![CDATA[Revista de Ciências Agrárias]]></journal-title>
<abbrev-journal-title><![CDATA[Rev. de Ciências Agrárias]]></abbrev-journal-title>
<issn>0871-018X</issn>
<publisher>
<publisher-name><![CDATA[Sociedade de Ciências Agrárias de Portugal]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S0871-018X2007000100054</article-id>
<title-group>
<article-title xml:lang="pt"><![CDATA[Metabolitos secundários como fontes de bioherbicidas: situação actual e perspectivas]]></article-title>
<article-title xml:lang="en"><![CDATA[Secondary metabolites as sources of bioherbicides: present situation and perspectives]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Dias]]></surname>
<given-names><![CDATA[L.S.]]></given-names>
</name>
<xref ref-type="aff" rid="A01"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Dias]]></surname>
<given-names><![CDATA[A.S.]]></given-names>
</name>
<xref ref-type="aff" rid="A01"/>
</contrib>
</contrib-group>
<aff id="A01">
<institution><![CDATA[,Universidade de Évora Centro de Ecologia e Ambiente ]]></institution>
<addr-line><![CDATA[Évora ]]></addr-line>
<country>lsdias@uevora.pt</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>01</month>
<year>2007</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>01</month>
<year>2007</year>
</pub-date>
<volume>30</volume>
<numero>1</numero>
<fpage>510</fpage>
<lpage>517</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://scielo.pt/scielo.php?script=sci_arttext&amp;pid=S0871-018X2007000100054&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://scielo.pt/scielo.php?script=sci_abstract&amp;pid=S0871-018X2007000100054&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://scielo.pt/scielo.php?script=sci_pdf&amp;pid=S0871-018X2007000100054&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="pt"><p><![CDATA[Metabolitos secundários produzidos e libertados por plantas, bactérias e fungos estão envolvidos numa variedade de processos ecológicos, nomeadamente como semioquímicos e alelopatinos. Adicionalmente, e para além das suas possíveis funções ecológicas, muitos dos metabolitos secundários são fitotóxicos, constituindo uma fonte relativamente inexplorada de novos herbicidas. Solanum nigrum (erva-moira) é uma infestante importante e muito bem sucedida num grande número de culturas, nomeadamente hortícolas e será usada como exemplo principal das utilizações actuais de aleloquímicos vegetais bem como das perspectivas de utilização deste tipo de compostos como bioherbicidas. Nesse âmbito revêem-se as principais estratégias de pesquisa de bioherbicidas e apresenta-se o estado da arte dos modos de acção de aleloquímicos já comercializados como herbicidas (Bialaphos e PPT), patenteados (AAL-toxina) e em investigação, quer produzidos por plantas superiores (sorgoleona e derivados do cineol) quer de origem bacteriana (hidantocidina) e fúngica (fumonisinas, coletotriquina).]]></p></abstract>
<abstract abstract-type="short" xml:lang="en"><p><![CDATA[Secondary metabolites produced and released by plants, bacteria, and fungi are involved in a number of ecological processes, namely as semiochemicals and allelopathins. In addition, and beside their possible ecological roles, a greater number of secondary metabolites are phytotoxic and represent a relatively unexplored source of new herbicides. Solanum nigrum (black nightshade) is an important and successful weed in many crops, namely in horticulture, and will be used as a major example of actual and prospective uses of phytoallelochemicals as bioherbicides. Therefore, the main strategies for bioherbicides search are reviewed and the state of art of the modes of action of allelochemicals is presented, including those already in use as herbicides (Bialaphos and PPT), patented (AAL-toxin), and under investigation, whether produced by plants (sorgoleone and cineol derivatives), bacteria (hydantocidin) or fungi (fumonisins and colletotrichin).]]></p></abstract>
</article-meta>
</front><body><![CDATA[ <p align="center"><b>Metabolitos secundários como fontes de bioherbicidas: situação    actual e perspectivas </b></p>     <p align="center"><b>Secondary metabolites as sources of bioherbicides: present    situation and perspectives </b></p>     <p>&nbsp;</p>     <P align="center">L.S. Dias<Sup><a href="#1">1</a><a name="top1"></a></Sup> &amp;    A.S. Dias<Sup><a href="#1">1</a><a name="top1"></a> </Sup></P>     <p>&nbsp;</p>     <p align="center"><b>RESUMO </b></p>     <p>Metabolitos secundários produzidos e libertados por plantas, bactérias e fungos    estão envolvidos numa variedade de processos ecológicos, nomeadamente como semioquímicos    e alelopatinos. Adicionalmente, e para além das suas possíveis funções ecológicas,    muitos dos metabolitos secundários são fitotóxicos, constituindo uma fonte relativamente    inexplorada de novos herbicidas. </P>     <p><i>Solanum nigrum</i> (erva-moira) é uma infestante importante e muito bem    sucedida num grande número de culturas, nomeadamente hortícolas e será usada    como exemplo principal das utilizações actuais de aleloquímicos vegetais bem    como das perspectivas de utilização deste tipo de compostos como bioherbicidas.  </P>     <p>Nesse âmbito revêem-se as principais estratégias de pesquisa de bioherbicidas    e apresenta-se o estado da arte dos modos de acção de aleloquímicos já comercializados    como herbicidas (Bialaphos e PPT), patenteados (AAL-toxina) e em investigação,    quer produzidos por plantas superiores (sorgoleona e derivados do cineol) quer    de origem bacteriana (hidantocidina) e fúngica (fumonisinas, coletotriquina).  </P>     <p>&nbsp;</p>     ]]></body>
<body><![CDATA[<p align="center"><b>ABSTRACT </b></p>     <p>Secondary metabolites produced and released by plants, bacteria, and fungi    are involved in a number of ecological processes, namely as semiochemicals and    allelopathins. In addition, and beside their possible ecological roles, a greater    number of secondary metabolites are phytotoxic and represent a relatively unexplored    source of new herbicides. </P>     <p><i>Solanum nigrum</i> (black nightshade) is an important and successful weed    in many crops, namely in horticulture, and will be used as a major example of    actual and prospective uses of phytoallelochemicals as bioherbicides. </P>     <p>Therefore, the main strategies for bioherbicides search are reviewed and the    state of art of the modes of action of allelochemicals is presented, including    those already in use as herbicides (Bialaphos and PPT), patented (AAL-toxin),    and under investigation, whether produced by plants (sorgoleone and cineol derivatives),    bacteria (hydantocidin) or fungi (fumonisins and colletotrichin). </P>     <p>&nbsp;</p>     <p>Texto completo disponível apenas em PDF.</p>     <p>Full text only available in PDF format.</p>     <p>&nbsp;</p>     <p align="center"><b>REFERÊNCIAS BIBLIOGRÁFICAS </b></p>     <!-- ref --><p>Abbas, H.K. &amp; Boyette, C.D. 1992. Phytotoxicity of fumonisin B1 on weed    and crop species. <i>Weed Technology</i>, <b>6</b>: 548-552. &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;[&#160;<a href="javascript:void(0);" onclick="javascript: window.open('/scielo.php?script=sci_nlinks&ref=000022&pid=S0871-018X200700010005400001&lng=','','width=640,height=500,resizable=yes,scrollbars=1,menubar=yes,');">Links</a>&#160;]<!-- end-ref --><p>Abbas, H.K. &amp; Boyette, C.D. 1993. Biological control of weeds using AAL-toxin.    United States Patent Number 5,256,628, dated October 26, 1993. </P>     <p>Abbas, H.K. &amp; Duke, S.O. 1995. Phytotoxins from plant pathogens as potential    herbicides. <i>Journal of Toxicology – Toxin Reviews</i>, <b>14</b>: 523-543.  </P>     <p>Abbas, H.K., Boyette, C.D., Hoagland, R.E. &amp; Vesonder, R. F. 1991. Bioherbicidal    potential of <i>Fusarium moliniforme</i> and its phytotoxin, fumonisin. <i>Weed    Science</i>, <b>39</b>: 673-677. </P>     <p>Abbas, H.K., Smeda, R.J., Gerwick, B.C. &amp; Shier, W.T. 1999. Fumonisin B1    from the fungus <i>Fusarium moliniforme</i> causes contact toxicity to plants:    evidence from studies with biosynthetically labelled toxin. <i>Journal of Natural    Toxins</i>, <b>8</b>: 405-420. </P>     <p>Abbas, H.K., Vesonder, R.F., Boyette, C.D. &amp; Peterson, S. W. 1993. Phytotoxicity    of AAL-toxin and other compounds produced by <i>Alternaria alternata</i> to    jimsonweed (<i>Datura stramonium</i>). <i>Canadian Journal of Botany</i>, <b>71</b>:    155-160. </P>     <p>Abbas, H.K., Duke, S.O., Merril Jr, A.H., Wang, E. &amp; Shier, W.T. 1998a.    Phytotoxicity of australli-fungin, AAL-toxins and fumonisin B1 to <i>Lemna pausicostata</i>.    <i>Phytochemistry</i>, <b>47</b>: 1509-1514. </P>     <p>Abbas, H.K., Duke, S.O., Paul, R.N., Riley, R.T. &amp; Tanaka, T. 1995. AAL-toxin,    a potent natural herbicide which disrupts sphingolipid metabolism of plants.    <i>Pesticide Science</i>, <b>43</b>: 181-187. </P>     <p>Abbas, H.K., Paul, R.N., Riley, P.T., Tanaka, T. &amp; Shier, W.T. 1998b. Ultrastructural    effects of AAL-toxin TA from the fungus <i>Alternaria alternata</i> on black    nightshade (<i>Solanum nigrum</i> L.) leaf discs and correlation with measures    of toxicity. <i>Toxicon</i>, <b>36</b>: 1821-1832. </P>     <p>Bais, H.P., Vepachedu, R., Gilroy, S., Callaway, R.M. &amp; Vivanco, J.M. 2003.    Allelopathy and exotic plant invasion: from molecules and genes to species interactions.    <i>Science</i>, <b>301</b>: 1377-1380. </P>     <p>Barata, E.N., Mustaparta, H., Pickett, J.A., Wadhams, L.J. &amp; Araujo, J.    2002. Encoding of host and non-host plant odours by receptor neurones in the    eucalyptus woodborer, <i>Phoracantha semipunctata</i> (Coleoptera: Cerambycidae).    <i>Journal of Comparative Physiology A</i>, <b>188</b>: 121-133. </P>     ]]></body>
<body><![CDATA[<p>Bassett, I.J. &amp; Munro, D.B. 1985. The biology of Canadian weeds. 67. <i>Solanum    ptycanthum</i> Dun., <i>S. nigrum</i> L. and <i>S. sarrachoides</i> Sendt. <i>Canadian    Journal of Plant Sciences</i>, <b>65</b>: 401-414. </P>     <p>Bell, E.A. 1981. The physiological role(s) of secondary (natural) products.    <i>In</i> E. E. Conn (ed) <i>Secondary Plant Products</i>, pp. 1-19. Academic    Press, New York, USA. </P>     <p>Czarnota, M.A., Paul, R.N., Dayan, F.E., Nimbal, C.I. &amp; Weston, L.E. 2001.    Mode of action, localization of production, chemical nature, and activity of    sorgoleone: a potent PSII inhibitor in <i>Sorghum</i> spp. root exudates. <i>Weed    Technology</i>, <b>15</b>: 813-825. </P>     <p>Dias, A.S., Dias, L.S., Pereira, I.P. 2004. Activity of water extracts of <i>Cistus    ladanifer</i> and <i>Lavandula stoechas</i> in soil on germination and early    growth of wheat and <i>Phalaris minor</i>. <i>Allelopathy Journal</i>, <b>14</b>:    59-64. </P>     <p>Dias, L.S., Pereira, I.P. &amp; Dias, A.S. 1995. Evaluation of mediterranean    type vegetation for weedicide activity. <i>Allelopathy Journal</i>, <b>2</b>:    197-204. </P>     <p>Duke, S.O., Dayan, F.E. &amp; Rimando, A.M. 2000a. Natural products and herbicide    discovery. <i>In</i> A. H. Cobb &amp; R. C. Kirkwood (eds) <i>Herbicides and    their Mechanisms of Action</i>, pp. 105-133. CRC Press, Boca Raton, USA. </P>     <p>Duke, S.O, Dayan, F.E., Romagni, J.G. &amp; Rimando, A.M. 2000b. Natural products    as sources of herbicides: current status and future trends. <i>Weed Research</i>,    <b>40</b>: 99-111. </P>     <p>Duke, S.O., Gohbara, M., Paul, R. N. &amp; Duke, M. V. 1992. Colletotrichin    causes rapid membrane damage to plant cells. <i>Journal of Phytopathology</i>,    <b>134</b>: 289-305. </P>     <p>Einhellig, F.A. &amp; Souza, I.F. 1992. Phytotoxicity of sorgoleone found in    grain sorghum root exudates. <i>Journal of Chemical Ecology</i>, <b>18</b>:    1-11. </P>     <p>Fay, P.K. &amp; Duke, W.B. 1977. An assessment of allelopathic potential in    <i>Avena</i> germplasm. <i>Weed Science</i>, <b>25</b>: 224-228. </P>     ]]></body>
<body><![CDATA[<p>Gelderblom, W.C.A., Semple, E., Marasas, W. F. O. &amp; Farber, E. 1992. The    cancer-initiating potential of the fumonisin B mycotoxins. <i>Carcinogenesis</i>,    <b>13</b>: 433-437. </P>     <p>Gonzalez, V.M., Kazimir, J., Nimbal, C., Weston, L.A. &amp; Cheniae, G.M. 1997.    Inhibition of photosystem II electron transfer reaction by the natural product    sorgoleone. <i>Journal of Agricultural and Food Chemistry</i>, <b>45</b>: 1415-1421.  </P>     <p>Harborne, J.B. 1980. Plant phenolics. <i>In</i> E. A. Bell &amp; B. V. Charlwood    (eds) <i>Secondary Plant Products</i>, pp. 329-402, Springer-Verlag, Berlin,    Germany. </P>     <p>Harrington, P.M. &amp; Junk, M.E. 1994. Process for the preparation of (+)hydantocidin    and analogs thereof. United States Patent Number 5,354,868 dated October 11,    1994. </P>     <p>Harrington, P.M. &amp; Junk, M.E. 1996. Process and intermediates for the preparation    of (+)-hydantocidin and analogs thereof. United States Patent Number 5,543,510    dated August 6, 1996. </P>     <p>Heap, I. 2005. <i>The International Survey of Herbicide Resistant Weeds.</i>    Online. Internet. November 10, 2005. Available <a href="http://www.weedscience.org/In.asp" target="_blank">www.weedscience.com.</a>  </P>     <p>Hejl, A.M. &amp; Koster, K.L. 2004. The allelochemical sorgoleone inhibits    root H+-ATPase and water uptake. <i>Journal of Chemical Ecology</i>, <b>30</b>:    2181-2191. </P>     <p>Hoagland, R.E. 2001. Microbial allelochemicals and pathogens as bioherbicidal    agents. <i>Weed Technology</i>, <b>15</b>: 835-857. </P>     <p>Holm, L.G., Plucknett, D.L., Pancho, J.V. &amp; Herberger, J.P. 1977. <i>The    World's Worst Weeds. Distribution and Biology.</i> University Press of Hawaii,    Honolulu, USA. </P>     <p>Lockerman, R.H. &amp; Putnam, A.R. (1979) Evaluation of allelopathic cucumbers    (<i>Cucumis sativus</i>) as an aid to weed control. <i>Weed Science</i>, <b>27</b>:    54-57. </P>     ]]></body>
<body><![CDATA[<p>Macías, F.A., Molinillo, J.M.G., Chinchilla, D. &amp; Galindo, J.C.G. 2004.    Heliannanes – a structure-activity relationship (SAR) study. <i>In</i> F. A.    Macías, J.C.G. Galindo, J.M.G. Molinillo &amp; H.G. Cutler (eds) <i>Allelopathy:    Chemistry and Modes of Action of Allelochemicals</i>, pp. 103-124. CRC Press,    Boca Raton, USA. </P>     <p>Massantini, F., Caporali, F. &amp; Zellini, G. 1977. Evidence for allelopathic    control of weeds in lines of soybean. <i>Proceedings EWRS Symposium ‘The Different    Methods of Weed Control and their Integration’</i>, vol. 1, pp. 23-28. Uppsala,    Sweden. </P>     <p>Meazza, G., Scheffler, B.E., Tellez, M. R., Rimando, A.M., Romagni, J.G., Duke,    S.O., Nanayakkara, D., Khan, I. A., Abourashed, E. A. &amp; Dayan, F.E. 2002.    The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate    dioxygenase. <i>Phytochemistry</i>, <b>59</b>: 281-288.</P>     <p>Mothes, K. 1980. Historical introduction. <i>In</i> E. A. Bell &amp; B. V.    Charlwood (eds) <i>Secondary Plant Products</i>, pp. 1-10. Springer-Verlag,    Berlin, Germany. </P>     <p>Nakajima, M., Itoi, K., Takamatsu, Y., Kinoshita, T., Okazaki, T., Kawakubo,    K., Shindo, M., Honma, T., Tohjigamori, M. &amp; Haneishi, T. 1991. Hydantocidin:    a new compound with herbicidal activity from <i>Streptomyces hygroscopicus.    The Journal of Antibiotics</i>, <b>44</b>: 293-300. </P>     <p>Nimbal, C.I., Yerkes, C.N., Weston, L.A. &amp; Weller, S. C. 1996. Herbicidal    activity and site of action of the natural product sorgoleone. <i>Pesticide    Biochemistry and Physiology</i>, <b>54</b>: 73-83. </P>     <p>Putnam, A.R. &amp; Duke, W.B. 1974. Biological suppression of weeds: evidence    for allelopathy in accessions of cucumber. <i>Science</i>, <b>185</b>: 370-372.  </P>     <p>Rasmussen, J.A., Hejl, A.M., Einhellig, F. A. &amp; Thomas, J. A. 1992. Sorgoleone    from root exudate inhibits mitochondrial functions. <i>Journal of Chemical Ecology</i>,    <b>18</b>: 197-207. </P>     <P>Rimando, A.M., Dayan, F.E., Czarnota, M. A., Weston, L. A. &amp; Duke, S. O.    1998. A new photosystem II electron transfer inhibitor from <i>Sorghum bicolor.    Journal of Natural Products</i>, <b>61</b>: 927-930. </P>     <p>Rizvi, S.J.H. &amp; Rizvi, V. 1992. Exploitation of allelochemicals in improving    crop productivity. <i>In</i> S. J. H. Rizvi &amp; V. Rizvi (eds) <i>Allelopathy.    Basic and Applied Aspects</i>, pp. 444-472. Chapman &amp; Hall, London, UK.  </P>     ]]></body>
<body><![CDATA[<p>Romagni, J.G., Duke, S.O. &amp; Dayan, F.E. 2000. Inhibition of plant asparagine    synthetase by monoterpene cineoles. <i>Plant Physiology</i>, <b>123</b>: 725-732.  </P>     <p>Streibig, J.C., Dayan, F.E., Rimando, A.M. &amp; Duke, S.O. 1999. Joint action    of natural and synthetic photosystem II inhibitors. <i>Pesticide Science</i>,    <b>55</b>: 137-146. </P>     <p>Swain, T. 1977. Secondary compounds as protective agents. <i>Annual Review    of Plant Physiology</i>, <b>28</b>: 479-501. </P>     <p>Weller, R.F. &amp; Phipps, R. H. 1978/1979. A review of black nightshade (<i>Solanum    nigrum</i> L.). <i>Protection Ecology</i>, <b>1</b>: 121-139. </P>     <p>Williams, G.H. 1982. <i>Dictionary of Weeds of Western Europe</i>. Elsevier    Scientific Publishing Company, Amsterdam, The Netherlands. </P>     <p>Zimdahl, R.L. 1993. <i>Fundamentals of Weed Science</i>. Academic Press Inc.,    San Diego, USA. </P>     <p>&nbsp;</p>     <p><Sup><a href="#top1">1</a><a name="1"></a></Sup> Chemical Ecology Unit, Centro    de Ecologia e Ambiente, Universidade de Évora, Ap. 94, 7002-554 Évora; e-mail:    <a href="mailto:lsdias@uevora.pt">lsdias@uevora.pt</a> </P>      ]]></body><back>
<ref-list>
<ref id="B1">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Abbas]]></surname>
<given-names><![CDATA[H.K.]]></given-names>
</name>
<name>
<surname><![CDATA[Boyette]]></surname>
<given-names><![CDATA[C.D.]]></given-names>
</name>
</person-group>
<article-title xml:lang="en"><![CDATA[Phytotoxicity of fumonisin B1 on weed and crop species.]]></article-title>
<source><![CDATA[Weed Technology]]></source>
<year>1992</year>
<volume>6</volume>
<page-range>548-552</page-range></nlm-citation>
</ref>
</ref-list>
</back>
</article>
