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Synthesis and Chemistry of Agrochemicals V PDF

340 Pages·1998·9.34 MB·English
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Synthesis and Chemistry g 01 acs.or6.fw0 of Agrochemicals V bs.68 u0 p://p998- 5, 2012 | htt0.1021/bk-1 11 2 on June 998 | doi: 41 ed by 89.163.35.n Date: May 14, do oaati wnlblic ou DP In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. g 01 acs.or6.fw0 bs.68 u0 p://p998- 5, 2012 | htt0.1021/bk-1 11 2 on June 998 | doi: 41 ed by 89.163.35.n Date: May 14, do oaati wnlblic ou DP In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. 686 ACS SYMPOSIUM SERIES Synthesis and Chemistry of Agrochemicals V g 01 acs.or6.fw0 bs.68 u0 p://p998- 5, 2012 | htt0.1021/bk-1 ZDeonnec aR A. gBricauklteurr,a lE PDrIoTdOucRts 11 2 on June 998 | doi: BuJcoksmeapnh L Gab.o Fraetonryieess I,n EteDrnITatOioRn al 41 ed by 89.163.35.n Date: May 14, GrDeugPoornyt ASg. rBicualstuarraal bP,r oEdDuIcTtsO R do oaati ownlublic David A. Hunt, EDITOR DP American Cyanamid Company Developed from a symposium sponsored by the Division of Agrochemicals of the American Chemical Society, American Chemical Society, Washington, DC In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. ISBN 0-8412-3546-5 ISSN 0097-6156 This book is printed on acid-free, recycled paper. g 01 Copyright © 1998 American Chemical Society acs.or6.fw0 bs.68 Distributed by Oxford University Press u0 p://p998- 5, 2012 | htt0.1021/bk-1 11 42 on June 1998 | doi: All Rights Reserved. Reprographic copying beyond that permitted by ed by 89.163.35.n Date: May 14, bSotMooneA oclty thki,0oe p1ni sr9Cso 2 pov13epi0,dry m7eUr diioSgt ttrhAeh td1.a C0 tR o8laeen paoplryuefar b tn-uhlccinheceda a eUptCirto.e eSnrln.i ctoCfeeerrnoe, rsp eIeoynp frcrf io$r.go,d2h mu20t 2c.A0 t2Ai0oc CRtnp iS losuf.s o saeDr lw$ lois0orawe.ol2ceed5t d oDtp hffeor eiprrsv a epeigna ,e agtDenser dani inn asov l tt pehhuraiesssier,d do oaati permissions requests to ACS Copyright Office, Publications Division, wnlblic 1155 16th Street, N.W., Washington, DC 20036. ou DP The citation of trade names and/or names of manufacturers in this publication is not to be construed as an endorsement or as approval by ACS of the commercial products or services referenced herein; nor should the mere reference herein to any drawing, specification, chemical process, or other data be regarded as a license or as a conveyance of any right or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce, use, or sell any patented invention or copyrighted work that may in any way be related thereto. Registered names, trademarks, etc., used in this publication, even without specific indication thereof, are not to be considered unprotected by law. PRINTED IN THE UNITED STATES OF AMERICA In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. Advisory Board ACS Symposium Series Mary E. Castellion Omkaram Nalamasu ChemEdit Company AT&T Bell Laboratories Arthur Β. Ellis Kinam Park g 01 bs.acs.or686.fw0 JUenfifvreersyit yS o.f GWaisfcfonnesyin at Madison PKuardthuee rUinnieve Rrsit.y P orter p://pu998-0 Argonne National Laboratory Duke University 15, 2012 | htt10.1021/bk-1 UGLnauiwvnedrresaint yIc .oe Gf PKe.ao nKrsgal es mann TDMhoea urDtgiAnlaS Rs G Ar.o Tu. paS,n mInt ict. h 42 on June 1998 | doi: NRUnaibcivihesrcasori tdFy o Noofd .Ms L Gisosreooupurppi ky EMasitcmhaane Cl hDem. Ticaaly Cloor. ed by 89.163.35.n Date: May 14, CR.y WRnet.s hJeoaiharcn hAso In.n sMPtihtuaatrremy aacneouftifc al PLUanerRirkvoeeesr-yeDs aiΒtaryvc .ihos T fP Mohawircmhnisagceaennu dtic al do Roger A. Minear oaati William C. Walker ownlublic Uniavte Ursritbya noaf -ICllhinaomisp aign DuPont Company DP In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. Foreword X HE ACS SYMPOSIUM SERIES was first published in 1974 to provide a mechanism for publishing symposia quickly in book form. The pur pose of the series is to publish timely, comprehensive books devel oped from ACS sponsored symposia based on current scientific re search. Occasionally, books are developed from symposia sponsored acs.org 6.fw001 bisyt ryo thauedr ioerngcaen. izations when the topic is of keen interest to the chem bs.68 Before agreeing to publish a book, the proposed table of contents u0 p://p998- is reviewed for appropriate and comprehensive coverage and for in 15, 2012 | htt10.1021/bk-1 fWtDeorrchaeuefsstnts ttohoa efpt hpcberhoo aaoppukrtdie;a iretosent ,hc aeerroe.s v S pemoremveairyee- r wpbeaev p ioeearwrd sdei enmddt ra poytrdo ibu opcerr t otoeoxrv ycifd liunecda hclea odpam tciencpre srope rthdaaeenrnrec s etio va oedbnrde eetrtsdees .r. 42 on June 1998 | doi: jpeecrtsi oAansr, e aa n irnduc lmleu,ad noeundsl ycinr io ptrthisge ia nrvaeol lpurremespeeaasrr.ec dVh eipnrab cpaaetmirmse raarne-rpder aooddryiug ciftnoiaormln srae tvo. ife wpr epvai ed by 89.163.35.n Date: May 14, AouCsSly B pOuObKlisSh DedE PpAapReTrMs EarNeT n ot accepted. do oaati wnlblic ou DP In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. Preface 1 HE LAST HALF OF THE 20TH CENTURY has seen major changes in the synthesis and development of new agrochemicals. This whole period has been in a state of flux in most of the aspects of the design, synthesis, and development org 001 of new active materials. Now as the dawn of the 21st century approaches, we see s.pr ac6. various agricultural biotechnological efforts supplementing and replacing stan http://pubs.k-1998-068 dwlaaatrosdr yoa ngfcrioee cldtho eufmtoeridc aatlgosr . obIcet h aiepnmp tehicaear lslsa, theho aw1s9 e7bv0eeesr.,n tShdiamrta ibslatiiorcltayel,c lhyitn iaosll toaegrlseyod i sco lnevoaertr dthtiheae tp talhnaeas tcr eefage uwit 5, 2012 | 0.1021/b yearsT. he editors of these volumes have organized synthesis symposia at each ne 1oi: 1 ACS National meeting since 1984. These symposia have been sponsored by the ud Agrochemicals Division of the ACS. The aim of these symposia has been to on J98 | provide a forum for presenting the synthesis and chemistry of new agrochemical 5.42 4, 19 agents. These symposia have provided a focus for agrochemical synthesis 31 3.y chemists to share their best work. The current book has chapters taken from the 6a by 89.1Date: M Asyumgpuosts ioaf p1r9e9se4n ttherdo uagt h ththee WSaansh Finrgantocnis, cDo CA CAS CNSa Ntioantiaoln Mal eMetienegti nhgel dh eilnd thine ded on spring of 1997. Each of the chapter authors was requested to present the current oaati status of the work at the time of preparation of the manuscript. In many cases wnlblic considerably more effort has been done since the work was presented at the ou D P meeting. These chapters present a unique look into the discovery process of our current and future agrochemical products. Not all of the chapters represent mate rials that will eventually be commercialized. It is hoped that these chapters will also provide a learning experience both for those working in this field and for others interested in the biological effects of organic molecules. As with the previous volumes, our goal is to inform the reader of the current trends in research for safe, efficient, biologically active agrochemicals. The or ganization of this book is similar to that of the preceding volumes. After the overview chapter there is a section dedicated to Dr. Marinus Los and his impor tant discovery of the Imidazolinone herbicides. The next section describes the discovery of new herbicides and plant control materials. The following section deals with the control of insects, acarids, and nematodes. The final section cov ers the control of plant fungal diseases. xi In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. Acknowledgments We express our thanks to the authors who have shared with us the details of their interesting research results—first at the symposia and here now in going that extra mile in preparing the chapters ready for publication. We hope that you our readers—whether you are our fellow synthesis chemists, or microbiologists, entomologists, plant physiologists, biotechnologists, or medicinal and pharma ceutical chemists—will find the chapters interesting, useful and above all stim ulating! Last, but not least, we also wish to thank our employers, Zeneca Ag Prod ucts, Buckman Laboratories International, DuPont, and American Cyanamid Company, without their generous support of these symposia, this volume and the previous ones could not have been published. org 001 s.pr ac6. DON R. BAKER http://pubs.k-1998-068 ZW12een0se0tce Sarno A uRgth eP s4er7oatdrhcu hcS tCtsr eeentt er 5, 2012 | 0.1021/b Richmond, CA 94804-0024 ne 1oi: 1 JOSEPH G. FENYES n Ju8 | d Buckman Laboratories International o9 1256 North McLean Boulevard 5.42 4, 19 Memphis, TN 38108 31 3.y 6a 1M by 89.Date: GDRuEPGonOtR AYg Sri.c BuAltuSrAaRl APBro ducts ded on Stine-Haskell Research Center oaati Newark, DE 1714 wnlblic ou DP DAVID A. HUNT American Cyanamid Company P.O. Box 400 Princeton, NJ 08543 xii In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998. Chapter 1 Synthesis of Agrochemicals and Agricultural Biotechnology Entering the 21st Century David A. Hunt, Don R. Baker, Joseph G. Fenyes, and Gregory S.B asarab 1Cyanamid Agricultural Research Center, American Cyanamid Company, P.O. acs.org 6.ch001 2Zeneca AgriculturaBl Poxro 4d0u0c, tsP,r 1in20ce0t oSno,u NthJ 4078t5h43 S-0tr4e0e0t, Richmond, CA 94804 5, 2012 | http://pubs.0.1021/bk-1998-068 3Buckm4Satinn eL-Habaosrkaetlolr Riese seInartMecNrhenem waCtpaeiohrnknitsea,,r lDT,, NEDIn u3c1P.89,o 17n1102t485 A6 gNriocrutlhtu MraclL Peraond uBcotusl,e vard, ne 1oi: 1 The last few years have been witness to dramatic changes in the ud agrochemical synthesis field. Since many of the approaches of the 2 on J998 | agrochemical sector to finding new active agents are similar to those in 41 the pharmaceutical field, the newer technologies developed for 163.35.May 14, Aphmaromngac tehuetsicea la rree sceoamrcbhi nhaatvorei able cehne memisbtrryac aendd bryo baogtrioccsh seymntihceasli rse saesa wrcehl.l ded by 89.on Date: acposrom acgmegsesrre.c sisRailvo ebs ooatucircqcsue iassr.i teio aTnls hooifs i nladcrergeliaevs ecinrogsm lygpr obeueanitnedrg l ieibmnrpapurlitoesys e fidnrot ofmo rth atchea eds esccmrreeiecenn ianinngdg ownloaublicati pnerowce slesa ditss eclfo.m Tphouen pdrsim. Te hgeo able itste tro nseawtis flyea tdhse tehvuesr ginecnreeraasteindg anreee dth feonr DP optimized by more conventional means or else by means of automated synthesis of more directed compound libraries. Consequently, the potential for agrochemical scientists to continue to provide safer, lower use-rate, more environmentally benign crop protection agents remains high. Concurrently during the past decade, great strides have been made in the adaptation and integration of biotechnology to agricultural production. Much of the work in this area has focused in developing new biological methods of pest control, crops with engineered resistance to pests and herbicides, and products with higher nutritional content. Overall this new technology promises to reduce the environmental load of chemical pesticides. While the development of molecular biology and its subsequent application to agriculture has been no less than spectacular, it has raised many questions concerning the landscape of pest control methodology in the future of global agriculture, particularly with regard to the place of traditional synthesis chemistry. © 1998American Chemical Society 1 In Synthesis and Chemistry of Agrochemicals V; Baker, D., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998.

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Content: Synthesis of agrochemicals and agricultural biotechnology entering the 21st century / David A. Hunt, Don R. Baker, Joseph G. Fenyes, and Gregory S. Basarab -- Anomalies and the discovery of the imidazolinone herbicides / Marinus Los -- The discovery of the imidazolinone herbicides from the
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