About the Author xiii
Preface xv

1 Significance of Fungicides and Antifungals for Agriculture and Medicine 1
1.1 Terminology 1
1.2 History 2
1.3 Demand 4
1.4 Cross-Industry 7
1.5 Innovation 10

2 Allylamine Antifungals: History, Activity, Synthesis, Resistance, MoA, and SAR 25
2.1 Products 25
2.2 History 26
2.3 Mode of Action 26
2.4 Biological Activity and Spectrum 28
2.5 Resistance 31
2.6 Synthesis 31
2.7 Structure–Activity Relationships and Analogs 34

3 Polyene Antifungals: History, Activity, Synthesis, Resistance, MoA, and SAR 43
3.1 Products 43
3.2 History 44
3.3 Mode of Action 45
3.4 Biological Activity and Spectrum 48
3.5 Resistance 51
3.6 Synthesis 52
3.7 Structure–Activity Relationships and Analogs 55

4 Echinocandin Antifungals: History, Activity, Synthesis, Resistance, MoA, and SAR 69
4.1 Products 69
4.2 History 71
4.3 Mode of Action 71
4.4 Biological Activity and Spectrum 74
4.5 Resistance 77
4.6 Synthesis 78
4.7 Structure–Activity Relationships and Analogs 82

5 Azole Antifungals and DMI Fungicides: History, Activity, Synthesis, Resistance, MoA, and SAR 95
5.1 Products 95
5.2 History 99
5.3 Mode of Action 102
5.4 Biological Activity and Spectrum 104
5.5 Resistance 109
5.6 Synthesis 111
5.7 Structure–Activity Relationships and Analogs 114

6 Strobilurin Fungicides: History, Activity, Synthesis, Resistance, MoA, and SAR 135
6.1 Products 135
6.2 History 136
6.3 Mode of Action 140
6.4 Biological Activity and Spectrum 142
6.5 Resistance 144
6.6 Synthesis 146
6.7 Structure–Activity Relationships and Analogs 150

7 Succinate Dehydrogenase Inhibiting (SDHI) Fungicides: History, Activity, Synthesis, Resistance, MoA, and SAR 165
7.1 Products 165
7.2 History 168
7.3 Mode of Action 170
7.4 Biological Activity and Spectrum 172
7.5 Resistance 174
7.6 Synthesis 175
7.7 Structure–Activity Relationships and Analogs 181

8 Oomycetes-selective Fungicides: History, Activity, Synthesis, Resistance, MoA, and SAR 193
8.1 Introduction 193
8.2 Phenylamides 194
8.3 Oomycetes-selective Complex III Inhibitors 198
8.4 Carboxylic Acid Amide Fungicides 203
8.5 Oxysterol-binding Protein Inhibitors 209

9 Fungicides and Antifungals with a Novel Mode of Action: Inhibitors of Dihydroorotate Dehydrogenase, Glycosylphosphatidylinositol-anchored Proteins, Aminoacyl-tRNA Synthetases, and Histone Deacetylase 225
9.1 Introduction 225
9.2 Inhibitors of Dihydroorotate Dehydrogenase 226
9.3 Inhibitors of Glycosylphosphatidylinositol-anchored Proteins 230
9.4 Inhibitors of Aminoacyl-tRNA Synthetases 234
9.5 Inhibitors of Histone Deacetylase 237

Index 249