Song / Yang / Jin Environment-Friendly Antiviral Agents for Plants

1. Auflage 2011
ISBN: 978-3-642-03692-7
Verlag: Springer
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, 305 Seiten

Plant virus disease is a worldwide threat to agriculture. Environment-Friendly Antiviral Agents for Plants systematically describes the basic theory, new ideas, and new methods to discover novel antiviral agents through research on plant immune activation. The cutting-edge research methodology, technology and progress on novel antiviral agent innovation are systematically described. With abundant illustrations and figures, the book is intended for researchers and practitioners in the fields of pesticide science, plant protection, organic chemistry, fine chemicals, applied chemistry, environment chemistry and agriculture science. Dr. Baoan Song and Dr. Song Yang are professors at the Center for R&D of Fine Chemicals, Guizhou University, China; Mr. Linhong Jin and Dr. Pinaki S. Bhadury are associate professors there.

Autoren/Hrsg.

Song, Baoan

Yang, Song

Jin, Lin-Hong

Bhadury, Pinaki S.

Inhaltsverzeichnis

1;Title Page ;2
2;Copyright Page ;3
3;Foreword;4
4;Preface;6
5;Table of Contents ;11
6;Introduction;17
7;Chapter 1 Studies on a-Aminophosphonates with Antiviral Activity;22
7.1;1.1 Organocatalytic Synthesis and Antiviral Activity of Asymmetric - a Aminophosphonates;22
7.1.1;1.1.1 Introduction;22
7.1.2;1.1.2 Materials and Methods;23
7.1.2.1;1.1.2.1 General;23
7.1.2.2;1.1.2.2 Synthesis and Characterization of Chiral Bronsted Catalyst 1.4 and Intermediates;24
7.1.2.3;1.1.2.3 General Procedure for Aldimines 1.2;25
7.1.2.4;1.1.2.4 General Procedure for Fluorinated Asymmetric a-aminophosphonates 1.5;26
7.1.2.5;1.1.2.5 Antiviral Biological Assay;26
7.1.3;1.1.3 Results and Discussion;27
7.1.4;1.1.4 Conclusions;33
7.2;1.2 Synthesis & Bioactivity of a-Aminophosphonates Containing Amide Moiety;34
7.2.1;1.2.1 Introduction;34
7.2.2;1.2.2 Materials and Methods;35
7.2.3;1.2.3 Results and Discussion;37
7.2.4;1.2.4 Conclusions;39
7.3;1.3 Green Synthesis & Bioactivity of a- Aminophosphonates Containing an Alkoxyethyl Moiety;40
7.3.1;1.3.1 Introduction;40
7.3.2;1.3.2 Materials and Methods;41
7.3.3;1.3.3 Results and Discussion;42
7.3.4;1.3.4 Conclusions;45
7.4;1.4 Green Synthesis & Bioactivity of Brominated a- Aminophosphonates;46
7.4.1;1.4.1 Introduction;46
7.4.2;1.4.2 Materials and Methods ;47
7.4.3;1.4.3 Results and Discussion;48
7.4.4;1.4.4 Conclusions;51
7.5;1.5 Synthesis & Bioactivity of a-Aminophosphonates Containing Trifluorinated Methyl Moiety;51
7.5.1;1.5.1 Introduction;51
7.5.2;1.5.2 Materials and Methods;52
7.5.2.1;1.5.2.1 Instruments;52
7.5.2.2;1.5.2.2 General procedure for the preparation of products 1.25a-1.25i;53
7.5.3;1.5.3 Results and Discussion;54
7.5.3.1;1.5.3.1 Chemistry;54
7.5.3.2;1.5.3.2 Biological Activity;58
7.5.4;1.5.4 Conclusions;59
7.6;1.6 Synthesis & Bioactivity of Chiral a-Aminophosphonates Containing Fluorine Moiety;59
7.6.1;1.6.1 Introduction;59
7.6.2;1.6.2 Materials and Methods;60
7.6.3;1.6.3 Results and Discussion;62
7.6.4;1.6.4 Conclusions;68
7.7;1.7 Green Synthesis of a-Aminophosphonates Containing Bromine and Fluorine under Ultrasonic Irradiation;69
7.7.1;1.7.1 Introduction;69
7.7.2;1.7.2 Materials and Methods;70
7.7.2.1;1.7.2.1 Apparatus and analysis;70
7.7.3;1.7.3 Results and Discussion;70
7.7.4;1.7.4 Conclusions;72
7.8;1.8 Synthesis & Bioactivity of a-Aminophosphonates Containing Isoxazole Moiety;73
7.8.1;1.8.1 Introduction;73
7.8.2;1.8.2 Materials and Methods;74
7.8.3;1.8.3 Results and Discussion;75
7.8.3.1;1.8.3.1 Crystal structure of 1.33c;77
7.8.4;1.8.4 Conclusions;79
7.9;1.9 Synthesis & Bioactivity of a-Aminophosphonates Containing Benzothiazole Moiety;81
7.9.1;1.9.1 Introduction;79
7.9.2;1.9.2 Materials and Methods;80
7.9.3;1.9.3 Results and Discussion;81
7.9.4;1.9.4 Conclusions;86
7.10; 1.10 Chiral Separation & Bioactivity of a-Aminophosphonates Containing Benzothiazole Moiety ;86
7.10.1;1.10.1 Introduction;86
7.10.2;1.10.2 Materials and Methods;87
7.10.2.1;1.10.2.1 Chemicals;87
7.10.2.2;1.10.2.2 Equipments;87
7.10.2.3;1.10.2.3 Instrumentation and Chromatographic conditions;88
7.10.2.4;1.10.2.4 Antiviral Bioassay;88
7.10.3;1.10.3 Results and Discussion;89
7.10.3.1;1.10.3.1 Analytical HPLC;89
7.10.3.2;1.10.3.2 Semi-preparative HPLC;95
7.10.3.3;1.10.3.3 Antiviral activity;97
7.10.4;1.10.4 Conclusions;99
7.11;1.11 Crystal Structure of O,O-Dipropyl-a-aminophosphonate Containing Benzothiazole Moiety;99
7.11.1;1.11.1 Introduction;99
7.11.2;1.11.2 Materials and Methods;99
7.11.3;1.11.3 Results and Discussion;100
7.12;References;101
8;Chapter 2 Synthesis, Characterization and Antiviral Activity of Cyanoacrylates and Derivatives;109
8.1;2.1 Synthesis and Antivival Activity of Cyanoacrylates Containing Phosphonyl Moiety;109
8.1.1;2.1.1 Introduction;109
8.1.2;2.1.2 Materials and Methods;110
8.1.3;2.1.3 Results and Discussion;111
8.1.4;2.1.4 Conclusions;116
8.2;2.2 Synthesis and Bioactivity of Cyanoacrylate Derivatives Containing Pyridine Moiety;116
8.2.1;2.2.1 Introduction;116
8.2.2;2.2.2 Materials and Methods;117
8.2.3;2.2.3 Results and Discussion;118
8.2.4;2.2.4 Conclusions;121
8.3;2.3 Preparation of Chiral Cyanoarylate Derivatives under Microwave Irradiation;121
8.3.1;2.3.1 Introduction;121
8.3.2;2.3.2 Materials and Methods;122
8.3.3;2.3.3 Results and Discussion;123
8.3.4;2.3.4 Conclusions;126
8.4; 2.4 Preparation of Chiral Cyanoacylate Derivatives from Phenylethanamine ;126
8.4.1;2.4.1 Introduction;126
8.4.1.1;2.4.2 Materials and Methods;128
8.4.1.1.1;2.4.2.1 Synthetic Procedures;128
8.4.1.1.2;2.4.2.2 General procedure for the preparation of intermediates 2.11a-2.11d;128
8.4.1.1.3;2.4.2.3 General procedure for the preparation of title compounds 2.12;128
8.4.1.1.4;2.4.2.4 Crystal structure determination;129
8.4.1.1.5;2.4.2.5 Antiviral Biological Assay;129
8.4.1.1.6;2.4.2.6 Herbicidal activity bioassay;129
8.4.1.1.7;2.4.2.7 MTT Assay against Cell Viability and Proliferation;129
8.4.1.2;2.4.3 Results and Discussion;129
8.4.1.2.1;2.4.3.1 Synthesis;129
8.4.1.2.2;2.4.3.2 Antiviral Activity;131
8.4.1.2.3;2.4.3.3 Herbicidal activity;132
8.4.1.2.4;2.4.3.4 Antiproliferation activity;132
8.4.1.2.5;2.4.3.5 Crystal Structure Analysis;133
8.4.1.3;2.4.4 Conclusions;134
8.5;2.5 Preparation and Antiviral Activity of Chiral Cyanoacylate Derivatives from Aryl (Heterocyclic) Amine;134
8.5.1;2.5.1 Introduction;134
8.5.2;2.5.2 Materials and Methods;135
8.5.2.1;2.5.2.1 General procedure for the preparation of intermediates 2.14a-2.14d;136
8.5.2.2;2.5.2.2 General procedure for the preparation of title chiral compounds 2.15;136
8.5.2.3;2.5.2.3 Crystal structure determination;136
8.5.2.4;2.5.2.4 Protection and inactivation and cure effect of compound against TMV in vivo;136
8.5.2.5;2.5.2.5 Determination of PAL and POD and SOD activity;136
8.5.2.6;2.5.2.6 RT-PCR assay;136
8.5.2.7;2.5.2.7 Semi-quantity PCR for expression of gene;137
8.5.2.8;2.5.2.8 The relative quantification real-time PCR for expression of the target gene;137
8.5.2.9;2.5.2.9 Statistical analysis;137
8.5.3;2.5.3 Chemistry;138
8.5.3.1;2.5.3.1 Synthesis of novel chiral cyanoacrylate derivatives.;138
8.5.3.2;2.5.3.2 Crystal structure analysis.;139
8.5.4;2.5.4 Antiviral Activity;140
8.5.4.1;2.5.4.1 Preliminary antiviral activity assay;140
8.5.4.2;2.5.4.2 Effect of (R)-2.15p treatment on PAL, POD and SOD activity in tobacco.;140
8.5.4.3;2.5.4.3 Gene expression analysis of PR-1a and PR-5 in (R)-2.15-treatedtobacco leaf;142
8.5.5;2.5.5 Discussion;143
8.5.6;2.5.6 Conclusions;144
8.6;2.6 Preparation and Antiviral Activity of Chiral Cyanoacylate Derivatives Containing -Aminophosphonate Moiety;144
8.6.1;2.6.1 Introduction;144
8.6.2;2.6.2 Materials and Methods;145
8.6.3;2.6.3 Results and Discussion;146
8.6.4;2.6.4 Conclusions;150
8.7;2.7 Crystal Structure elucidation of Cyanoacrylates;151
8.7.1;2.7.1 Crystal Structure of (E)-Ethyl-3-[(S)-1-phenylethylamino]- 3-[4-(trifluoromethyl)- phenylamino]-2-cyanoacrylate;151
8.7.2;2.7.2 Characterization of Two Chiral Isomers of (E)-Ethyl-3- [(R) or (S)-1-phenylethyl amino]-3-[4-nitrophenylamino]-2- cyanoacrylate;157
8.8;References;161
9;Chapter 3 Synthesis and Antiviral Activity of Chiral Thiourea Derivatives;166
9.1;3.1 Chiral Thiourea Deravatives from Primary Amine and Isocyanate;166
9.1.1;3.1.1 Introduction;166
9.1.2;3.1.2 Materials and Methods;167
9.1.3;3.1.3 Results and Discussion;168
9.1.4;3.1.4 Conclusions;173
9.2;3.2 Chiral Thiourea Derivatives Containing a-Aminophosphonate Moiety;173
9.2.1;3.2.1 Introduction;173
9.2.2;3.2.2 Materials and Methods;175
9.2.3;3.2.3 Results and Discussion;176
9.2.4;3.2.4 Conclusions;179
9.3;References;179
10;Chapter 4 The Heterocyclic Antiviral Agents;182
10.1;4.1 Pyrazole Derivatives Containing Oxime Ester Moiety;182
10.1.1;4.1.1 Introduction;182
10.1.2;4.1.2 Materials and Methods;183
10.1.2.1;4.1.2.1 Analysis and Instruments;183
10.1.2.2;4.1.2.2 Preparation of pyrazolaldoxime ester derivatives (4.4a-4.4n);183
10.1.2.3;4.1.2.3 Crystal structure determination;184
10.1.2.4;4.1.2.4 Protection and inactivation and cure effect of compound against TMV in vivo;184
10.1.2.5;4.1.2.5 Determination of PAL and POD and SOD activity;184
10.1.2.6;4.1.2.6 RT-PCR assay;184
10.1.2.7;4.1.2.7 The relative quantification real-time PCR for expression of the targetgene;185
10.1.2.8;4.1.2.8 The primary spectroscopic study of compound 4.4l for TMV CP;185
10.1.2.9;4.1.2.9 The determination of quenching constants;186
10.1.2.10;4.1.2.10 The primary spectroscopic study of compound 4.4l for TMV RNA;186
10.1.2.11;4.1.2.11 Statistical analysis;186
10.1.3;4.1.3 Chemistry;186
10.1.3.1;4.1.3.1 Synthesis of novel pyrazole derivatives;186
10.1.3.2;4.1.3.2 Crystal structure analysis;187
10.1.4;4.1.4 Antiviral Activity;188
10.1.4.1;4.1.4.1 Preliminary antiviral activity assay;188
10.1.4.2;4.1.4.2 Effect of 4.4l treatment on PAL, POD and SOD activity in tobacco;189
10.1.4.3;4.1.4.3 Gene expression analysis of PR-1a and PR-5 in 4.4l-treated tobacco leaf;190
10.1.4.4;4.1.4.4 The primary spectroscopic study of 4.4l for TMV CP;191
10.1.5;4.1.5 Discussion;195
10.1.6;4.1.6 Conclusions;196
10.2;4.2 Pyrazole Derivatives Containing Oxime Ether Moiety;197
10.2.1;4.2.1 Introduction;197
10.2.2;4.2.2 Materials and Methods;199
10.2.3;4.2.3 Results and Discussion;200
10.2.4;4.2.4 Conclusions;204
10.3;4.3 Quinazolinone Derivatives;205
10.3.1;4.3.1 Introduction;205
10.3.2;4.3.2 Materials and Methods;206
10.3.3;4.3.3 Results and Discussion;208
10.3.4;4.3.4 Conclusions;215
10.4;References;215
11;Chapter 5 Innovation and Application of Environment-Friendly Antiviral Agents for Plants;220
11.1;5.1 Innovation of New Antiviral Agent Dufulin[N-[2-(4-methyl-benzothiazol)]- 2-ylamino-2-fluophenyl-O,O-diethyl phosphonate];220
11.1.1;5.1.1 Product Chemistry;221
11.1.2;5.1.2 Formulation of Dufulin;221
11.1.2.1;5.1.2.1 Formalation of 30% Dufulin suspension concentrate(SC);222
11.1.2.2;5.1.2.2 Formalation of 30% Dufulin wettable powder(WP);226
11.1.2.3;5.1.2.3 Formulations of 10% Dufulin Emulsion Concentrate(EC);228
11.1.3;5.1.3 Optimization of Synthetic Conditions in Lab Scale and Pilot Scale;231
11.1.3.1;5.1.3.1 Introduction;231
11.1.3.2;5.1.3.2 Materials and Methods;231
11.1.3.3;5.1.3.3 Results and Discussion;232
11.1.3.4;5.1.3.4 Conclusions;235
11.1.4;5.1.4 Toxicology Test;237
11.1.4.1;5.1.4.1 Introduction;237
11.1.4.2;5.1.4.2 Methods;238
11.1.4.3;5.1.4.3 Results and discussion;238
11.1.4.4;5.1.4.4 Conclusions;239
11.1.5;5.1.5 Field Trials;240
11.1.5.1;5.1.5.1 Introduction;240
11.1.5.2;5.1.5.2 Materials and methods;241
11.1.5.3;5.1.5.3 Results and Discussion;242
11.1.5.4;5.1.5.4 Conclusion;244
11.1.6;5.1.6 Pesticide Residue;244
11.1.6.1;5.1.6.1 Introduction;244
11.1.6.2;5.1.6.2 Materials and Methods;245
11.1.6.3;5.1.6.3 Results and Discussion;246
11.1.6.4;5.1.6.4 Conclusions;251
11.1.7;5.1.7 Environmental toxicology;251
11.1.7.1;5.1.7.1 Introduction;251
11.1.7.2;5.1.7.2 Materials and Methods;251
11.1.7.3;5.1.7.3 Results;252
11.1.7.4;5.1.7.4 Conclusion;253
11.1.8;5.1.8 Mode of Action;253
11.1.8.1;5.1.8.1 Introduction;253
11.1.8.2;5.1.8.2 Materials and Methods;254
11.1.8.3;5.1.8.3 Results and Discussion;259
11.1.8.4;5.1.8.4 Conclusions;270
11.1.8.5;References;270
11.1.9;5.1.9 Photolysis and Hydrolysis;271
11.1.9.1;5.1.9.1 Introduction;271
11.1.9.2;5.1.9.2 Materials and Methods;272
11.1.9.3;5.1.9.3 Results;275
11.1.9.4;5.1.9.4 Conclusions;284
11.1.10;5.1.10 Systemic Behaviors;286
11.1.10.1;5.1.10.1 Introduction;286
11.1.10.2;5.1.10.2 Materials and methods;286
11.1.10.3;5.1.10.3 Results and disccussion;289
11.1.10.4;5.1.10.4 Conclusions;292
11.1.10.5;References;292
11.2;5.2 GU188, 2-Cyanoacrylate Derivative, Candidate Antiviral Agent;293
11.2.1;5.2.1 Synthesis;293
11.2.1.1;5.2.1.1 Introduction;293
11.2.1.2;5.2.1.2 Materials and methods;293
11.2.1.3;5.2.1.3 Results and discussion;294
11.2.1.4;5.2.1.4 Conclusions;297
11.2.2;5.2.2 Analytical Method;297
11.2.2.1;5.2.2.1 Introduction;297
11.2.2.2;5.2.2.2 Materials and methods;298
11.2.2.3;5.2.2.3 Results and discussion;299
11.2.2.4;5.2.2.4 Conclusions;299
11.2.3;5.2.3 Bioassays and Field Trials;300
11.2.3.1;5.2.3.1 Introduction;300
11.2.3.2;5.2.3.2 Materials and methods;300
11.2.3.3;5.2.3.3 Results and Discussion;300
11.2.3.4;5.2.3.4 Conclusions;301
11.2.4;5.2.4 Toxicological Test;302
11.2.4.1;5.2.4.1 Introduction;302
11.2.4.2;5.2.4.2 Methods;302
11.2.4.3;5.2.4.3 Results and discussion;302
11.2.4.4;5.2.4.4 Conclusions;303
11.2.5;5.2.5 Action Mechanism;303
11.2.5.1;5.2.5.1 Introduction;303
11.2.5.2;5.2.5.2 Materials and Methods;304
11.2.5.3;5.2.5.3 Results and Discussion;304
11.2.5.4;5.2.5.4 Conclusions;308
11.3;5.3 Studies on the Development of Novel Amino-oligosaccharide;308
11.3.1;5.3.1 Introduction;308
11.3.2;5.3.2 Anti-TMV and Mechanism of Action;309
11.3.2.1;5.3.2.1 Anti-TMV bioassay;309
11.3.2.2;5.3.2.2 Mechanistic study;309
11.3.2.3;5.3.2.3 Effects of 0.5% amino-oligosaccharin aqua on tobacco defense enzyme;310
11.3.3;5.3.3 Industrialization;311
12;Index ;314