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E-raamat: Bioactive Heterocyclic Compound Classes - Pharmaceuticals: Agrochemicals [Wiley Online]

Edited by (Syngenta Crop Protection AG, Stein, Switzerland), Edited by (Abbott Laboratories, Abbott Park, USA)
  • Formaat: 302 pages
  • Ilmumisaeg: 12-Sep-2012
  • Kirjastus: Blackwell Verlag GmbH
  • ISBN-10: 3527664416
  • ISBN-13: 9783527664412
  • Wiley Online
  • Hind: 195,60 €*
  • * hind, mis tagab piiramatu üheaegsete kasutajate arvuga ligipääsu piiramatuks ajaks
  • Formaat: 302 pages
  • Ilmumisaeg: 12-Sep-2012
  • Kirjastus: Blackwell Verlag GmbH
  • ISBN-10: 3527664416
  • ISBN-13: 9783527664412
The chemistry of heterocycles is an important branch of organic chemistry. This is due to the fact that a large number of natural products,
e. g. hormones, antibiotics, vitamins, etc. are composed of heterocyclic structures. Often, these compounds show beneficial properties and are
therefore applied as pharmaceuticals to treat diseases or as insecticides, herbicides or fungicides in crop protection. This volume presents important agrochemicals. Each of the 21 chapters covers in a concise manner one class of heterocycles, clearly structured as follows:

* Structural formulas of most important examples (market products)
*Short background of history or discovery
* Typical syntheses of important examples
* Mode of action
* Characteristic biological activity
* Structure-activity relationship
* Additional chemistry information (e.g. further transformations, alternative syntheses, metabolic pathways, etc.)
* References

A valuable one-stop reference source for researchers in academia and industry as well as for graduate students with career aspirations in the
agrochemical chemistry.
Preface xi
List of Contributors
xiii
Introduction 1(2)
1 The Significance of Heterocycles for Pharmaceuticals and Agrochemicals
3(18)
Clemens Lamberth
Jurgen Dinges
1.1 Introduction
3(1)
1.2 Heterocycles as Framework of Biologically Active Compounds
4(2)
1.3 Fine-Tuning the Physicochemical Properties with Heterocycles
6(1)
1.4 Heterocycles as Prodrugs
6(1)
1.5 Heterocycles as Peptidomimetics
7(1)
1.6 Heterocycles as Isosteric Replacement of Functional Groups
8(3)
1.7 Heterocycles as Isosteric Replacement of Alicyclic Rings
11(2)
1.8 Heterocycles as Isosteric Replacement of other Heterocyclic Rings
13(8)
References
16(5)
Part I Herbicides
21(82)
2 Triazine Herbicides
23(16)
Andrew J.F. Edmunds
2.1 Introduction
23(1)
2.2 History
23(4)
2.3 Synthesis
27(4)
2.4 Mode of Action
31(3)
2.4.1 Point Mutation in psbA Gene
33(1)
2.4.2 Glutathione Conjugation
33(1)
2.4.3 Metabolic Resistance
34(1)
2.5 Biological Activity
34(1)
2.6 Structure-Activity Relationships
34(5)
References
37(2)
3 Pyrimidinyl and Triazinylsulfonylurea Herbicides
39(12)
Mary Ann Hanagan
Atul Puri
3.1 Introduction
39(1)
3.2 History
39(2)
3.2.1 Propyrisulfuron
41(1)
3.2.2 Metazosulfuron
41(1)
3.3 Synthesis
41(4)
3.4 Mode of Action
45(1)
3.5 Biological Activity
46(1)
3.6 Structure-Activity Relationship
47(4)
References
48(3)
4 Acetohydroxyacid Synthase Inhibiting Triazolopyrimidine Herbicides
51(10)
Timothy C. Johnson
Richard K. Mann
Paul R. Schmitzer
Roger E. Gast
4.1 Introduction
51(1)
4.2 History
51(2)
4.3 Synthesis
53(2)
4.4 Mode of Action
55(1)
4.5 Biological Activity
56(1)
4.6 Structure-Activity Relationship
57(4)
References
59(2)
5 HPPD-Inhibiting Benzoylpyrazole Herbicides
61(8)
Matthias Witschel
5.1 Introduction
61(1)
5.2 History
61(1)
5.3 Synthesis
62(2)
5.4 Mode of Action
64(2)
5.5 Biological Activity
66(1)
5.6 Structure-Activity Relationship
66(3)
References
68(1)
6 Pyridyloxyphenoxypropionate Herbicides: Inhibitors of Acetyl-CoA Carboxylase
69(14)
William G. Whittingham
6.1 Introduction
69(1)
6.2 History
69(2)
6.3 Synthesis
71(2)
6.4 Mode of Action
73(2)
6.5 Biological Activity
75(1)
6.6 Structure-Activity Relationships
76(7)
References
80(3)
7 Imidazolinone Herbicides
83(8)
Dale Shaner
7.1 Introduction
83(1)
7.2 History
83(2)
7.3 Synthesis
85(1)
7.4 Mode of Action
86(1)
7.5 Biological Activity
86(2)
7.6 Structure-Activity Relationship
88(3)
References
89(2)
8 Protoporphyrinogen-IX-Oxidase-Inhibiting Uracil Herbicides
91(12)
George Theodoridis
8.1 Introduction
91(1)
8.2 History
91(1)
8.3 Synthesis
92(2)
8.4 Mode of Action
94(1)
8.5 Biological Activity
94(3)
8.6 Structure-Activity Relationship
97(6)
References
100(3)
Part II Fungicides
103(92)
9 Benzimidazole Fungicides
105(14)
Laura Quaranta
9.1 Introduction
105(1)
9.2 History
105(3)
9.3 Synthesis
108(2)
9.4 Mode of Action
110(2)
9.5 Biological Activity
112(2)
9.6 Structure-Activity Relationship
114(5)
References
116(3)
10 Morpholine Fungicides for the Treatment of Powdery Mildew
119(10)
Clemens Lamberth
10.1 Introduction
119(1)
10.2 History
119(1)
10.3 Synthesis
120(2)
10.4 Mode of Action
122(1)
10.5 Biological Activity
123(1)
10.6 Structure-Activity Relationship
124(5)
References
126(3)
11 Sterol Biosynthesis Inhibiting Triazole Fungicides
129(18)
Paul Worthington
11.1 Introduction
129(1)
11.2 History
129(5)
11.3 Synthesis
134(4)
11.4 Mode of Action
138(2)
11.5 Biological Activity
140(1)
11.6 Structure-Activity Relationship
141(6)
References
143(4)
12 Methionine Biosynthesis-Inhibiting Anilinopyrimidine Fungicides
147(8)
Clemens Lamberth
12.1 Introduction
147(1)
12.2 History
147(1)
12.3 Synthesis
148(2)
12.4 Mode of Action
150(1)
12.5 Biological Activity
151(1)
12.6 Structure-Activity Relationship
151(4)
References
153(2)
13 Phenylpyrrole Fungicides
155(8)
Clemens Lamberth
13.1 Introduction
155(1)
13.2 History
155(1)
13.3 Synthesis
156(2)
13.4 Mode of Action
158(1)
13.5 Biological Activity
158(2)
13.6 Structure-Activity Relationship
160(3)
References
161(2)
14 Broad-Spectrum Fungicidally Active Pyrimidinyldioxy Strobilurins Inhibiting the Respiratory Chain
163(12)
Clemens Lamberth
14.1 Introduction
163(1)
14.2 History
163(2)
14.3 Synthesis
165(1)
14.4 Mode of Action
165(3)
14.5 Biological Activity
168(1)
14.6 Structure-Activity Relationship
169(6)
References
173(2)
15 Pyrazole Carboxamide Fungicides Inhibiting Succinate Dehydrogenase
175(20)
Harald Walter
15.1 Introduction
175(1)
15.2 History
175(2)
15.3 Synthesis
177(6)
15.4 Mode of Action
183(2)
15.5 Biological Activity
185(2)
15.5.1 The Foliar Pyrazole Carboxamides
185(1)
15.5.2 The Seed Treatment Pyrazole Carboxamides
186(1)
15.6 Structure-Activity Relationships
187(8)
Acknowledgements
191(4)
References
191(4)
Part III Insecticides
195(84)
16 Avermectin Insecticides and Acaricides
197(12)
Thomas Pitterna
16.1 Introduction
197(1)
16.2 History
197(2)
16.3 Synthesis
199(2)
16.4 Mode of Action
201(1)
16.5 Biological Activity
202(2)
16.6 Structure-Activity Relationship
204(5)
References
206(3)
17 Pyridine and Thiazole-Containing Insecticides as Potent Agonists on Insect Nicotinic Acetylcholine Receptors
209(16)
Peter Jeschke
17.1 Introduction
209(1)
17.2 History
209(2)
17.3 Synthesis
211(3)
17.4 Mode of Action
214(1)
17.5 Biological Activity
215(2)
17.6 Structure-Activity Relationship
217(8)
References
221(4)
18 Pyrazole and Pyrimidine Acaricides and Insecticides Acting as Inhibitors of Mitochondrial Electron Transport at Complex I
225(14)
Ottmar Franz Huter
18.1 Introduction
225(1)
18.2 History
225(2)
18.3 Synthesis
227(2)
18.4 Mode of Action
229(1)
18.5 Biological Activity
230(1)
18.6 Structure-Activity Relationship
230(9)
References
236(3)
19 Phenylpyrazole-Containing Fiprole Insecticides
239(12)
Stefan Schnatterer
19.1 Introduction
239(1)
19.2 History
239(2)
19.3 Synthesis
241(3)
19.4 Mode of Action
244(1)
19.5 Biological Activity
244(2)
19.6 Structure-Activity Relationship
246(5)
References
248(3)
20 Pyrazolylpyridine Activators of the Insect Ryanodine Receptor
251(14)
George P. Lahm
Thomas P. Selby
Thomas M. Stevenson
Daniel Cordova
I. Billy Annan
John T. Andaloro
20.1 Introduction
251(1)
20.2 History
251(2)
20.3 Synthesis
253(1)
20.4 Mode of Action
254(1)
20.5 Biological Activity
255(1)
20.6 Structure-Activity Relationships
256(9)
20.6.1 Rynaxypyr®
256(1)
20.6.2 R1 (6-Substituent of the Anthranilic Ring)
257(1)
20.6.3 R2 (4-Substituent of the Anthranilic Ring)
257(1)
20.6.4 R3 (Amide Residue)
257(1)
20.6.5 R4 (3-Pyrazole Substituent)
258(1)
20.6.6 R5 and A (N-Substituted Aryl or Heteroaryl Group)
258(1)
20.6.7 Cyazypyr™
258(4)
References
262(3)
21 Tetronic Acid Insecticides and Acaricides Inhibiting Acetyl-CoA Carboxylase
265(14)
Thomas Bretschneider
Reiner Fischer
Ralf Nauen
21.1 Introduction
265(1)
21.2 History
265(3)
21.3 Synthesis
268(1)
21.4 Mode of Action
269(2)
21.5 Biological Activity
271(3)
21.6 Structure-Activity Relationship
274(5)
References
277(2)
Index 279
Clemens Lamberth is a senior team leader in the crop protection research department of Syngenta AG, Switzerland. He studied chemistry at the Technical University of Darmstadt, Germany, where he obtained his Ph.D. under the supervision of Prof. Bernd Giese in 1990. Subsequently, he spent one and a half years as a postdoctoral fellow in the group of Prof. Mark Bednarski at the University of California at Berkeley, U.S.A. In 1992 Clemens Lamberth joined the agrochemical research department of Sandoz Agro AG, Switzerland, which is today, after two mergers, part of Syngenta Crop Protection AG. Since 20 years he is specialized in fungicide discovery. He was the organizer of the two-day session 'New Trends for Agrochemicals' at the 2nd EUCHEMS congress in Torino 2008. He is the author of 46 publications and 56 patents and the inventor of Syngenta's fungicide mandipropamid (Revus®, Pergado®).

Jürgen Dinges obtained his M.S. degree in organic chemistry at the Technical University in Darmstadt, Germany in 1988. He then joined the group of Prof. Frieder W. Lichtenthaler at the same University, where he received his Ph.D. degree in organic chemistry and chemical engineering in 1991. After being awarded a Feodor-Lynen scholarship from the Humboldt foundation, he spent 18 months as a postdoctoral fellow in the group of Prof. William G. Dauben at the University of California at Berkeley, U.S.A. In 1993, Jurgen Dinges joined the department for biochemistry at Syntex, U.S.A. and since 1995 he is working in the pharmaceutical research department at Abbott Laboratories, U.S.A. In 2009, he was a guest editor for Current Topics in Medicinal Chemistry for a special issue on Parkinson?s disease. He is an author of 17 publications and 23 patents and a co-inventor of more than 10 clinical drug development candidates.