Dendrenamide compound, bactericidal and use thereof

Description

Technical Field

[0001] The invention relates to the field of pesticides, and particularly relates to a dendrene amide compound, a bactericide and the use thereof.Background

[0002] Succinate dehydrogenase inhibitors (SDHIs) are bactericides which are used for preventing and treating diseases by acting on a complex II (also called succinate dehydrogenase or ubiquinone succinate reductase) on a respiratory electron transfer chain of mitochondria of pathogenic fungi to interfere the succinate dehydrogenase on the respiratory electron transfer chain to inhibit the functions of the mitochondria, prevent the mitochondria from generating energy, inhibit the growth of the pathogenic fungi and finally cause the death of the pathogenic fungi.

[0003] The succinate dehydrogenase inhibitor bactericide has become the most promising bactericide in recent years due to high efficiency, broad-spectrum fungicidal activity and relatively low resistance risk, and is concerned by various pesticide companies in the world.

[0004] WO2011151369 discloses N-[(het)arylethyl)] pyrazolecarboxamides or thiocarboxamides useful for the control of phytopathogenic fungi of plants. WO2014060520 discloses methods for treating plants against fungi resistant to fungicides using N-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide or thiocarboxamide derivatives.Disclosure of Invention

[0005] The invention aims to overcome the aforementioned defects of the prior art and provide a novel class of compounds having succinate dehydrogenase inhibitory effect.

[0006] In order to achieve the above object, the first aspect of the invention provides a dendrene amide compound having a structure shown in formula (I), wherein, in the formula (I), X is F; R 1< and R 2< are each independently selected from H, methyl, ethyl, n-propyl; R 31< , R32, R 33< , R 34< and R 35< are each independently selected from H, F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, trifluoromethyl, C 1-3 alkylsulfonyl, ethoxy, substituted or unsubstituted ethynyl; the optional substituents on R 31< , R 32< , R 33< , R 3< 4 and R 35< are selected from at least one of methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl; R 4< is cyclopropyl; R 51< is difluoromethyl; R 52< is methyl; R 61< and R 62< are each independently selected from H, F, Cl, Br.

[0007] The second aspect of the invention provides the use of the aforementioned compounds as succinate dehydrogenase inhibitors in pesticides.

[0008] The third aspect of the invention provides the use of the aforementioned compounds for controlling plant fungal diseases.

[0009] The fourth aspect of the invention provides a bactericide which comprises an auxiliary material and an active ingredient selected from at least one of the aforementioned compounds; the active ingredient is contained in the bactericide in an amount of 5% to 99.99% by weight.

[0010] The fifth aspect of the invention provides the use of the aforementioned bactericide for the control of fungal diseases in plants.

[0011] The dendrene amide compound provided by the invention has high activity of inhibiting succinate dehydrogenase, the dendrene amide compound has high control effect on fungal diseases, and the dendrene amide compound particularly has excellent control effect on erysiphe graminis, sphaerotheca fuliginea, wheat scab, rice bakanae disease, sclerotinia rot of colza, corn leaf spot, wheat stripe rust and cucumber gray mold.Detailed Description

[0012] The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and these ranges or values should be understood to encompass values close to these ranges or values. For numerical ranges, each range between its endpoints and individual point values, and each individual point value can be combined with each other to give one or more new numerical ranges, and such numerical ranges should be construed as specifically disclosed herein.

[0013] As described above, the first aspect of the invention provides a dendrene amide compound having the structure represented by formula (I), wherein, in the formula (I), R 1< and R 2< are each independently selected from H, methyl, ethyl, n-propyl; R 31< , R 32< , R 33< , R 34< and R 35< are each independently selected from H, F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, trifluoromethyl, C 1-3 alkylsulfonyl, ethoxy, substituted or unsubstituted ethynyl; the optional substituents on R 31< , R 32< , R 33< , R 34< and R 35< are selected from at least one of methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, R 4< is cyclopropyl; R 51< is difluoromethyl; R 52< is methyl; R 61< and R 62< are each independently selected from H, F, Cl, Br. Embodiment mode 1:

[0014] The compound shown in formula (I) is selected from at least one of compounds 1 to 219.

[0015] The above compounds provided by the invention have significantly higher inhibitory activity against succinate dehydrogenase. It is a good succinate dehydrogenase inhibitor.

[0016] The invention has no special requirements for the specific preparation method of the above-mentioned compounds, and those skilled in the art can select an appropriate synthetic route to prepare the compounds according to the structural formula provided by the present invention in combination with the known synthetic methods in the field of organic chemistry. Several specific synthetic methods are provided below and in the examples of the invention by way of example, and the person skilled in the art should not be understood as limiting the invention.

[0017] Illustratively, the compound of the formula (I) of the invention is prepared by a method comprising the following steps:

[0018] The synthesis route provided by the invention can comprise some post-treatment means known in the art to improve the purity of the target product and the like.

[0019] As mentioned above, the second aspect of the invention provides the use of the aforementioned compounds as succinate dehydrogenase inhibitors in pesticides.

[0020] As mentioned above, the third aspect of the invention provides the use of the aforementioned compounds for controlling plant fungal diseases.

[0021] As mentioned above, the fourth aspect of the invention provides a bactericide which comprises an auxiliary material and an active ingredient selected from at least one of the aforementioned compounds; the active ingredient is contained in the bactericide in an amount of 5% to 99.99% by weight.

[0022] Preferably, the dosage form of the bactericide is at least one selected from emulsifiable concentrates, suspending agents, wettable powders, dusts, granules, aqueous solutions, poison baits, mother liquors and mother powders.

[0023] The invention has no special requirements for the specific types of the auxiliary materials in the bactericide, and the skilled person can select the corresponding auxiliary materials known in the art to prepare the bactericide of the invention according to the dosage form, and the invention is not described in detail herein, and the skilled person should not be construed as limiting the invention.

[0024] As mentioned above, the fifth aspect of the invention provides the use of the aforementioned bactericide for the control of fungal diseases in plants.

[0025] Preferably, the plant fungal diseases is selected from at least one of erysiphe graminis, sphaerotheca fuliginea, wheat scab, rice bakanae disease, sclerotinia rot of colza, corn leaf spot, wheat stripe rust and cucumber gray mold.

[0026] The invention will be described in detail below by way of examples. In the following examples, the raw materials used are all ordinary commercial products unless otherwise specified.

[0027] The room temperature in the following examples means 25 ± 2 °C unless otherwise specified.

[0028] The objective compounds in the following examples are prepared by the following synthetic routes, unless otherwise specified. Specifically, the method comprises the following steps: when R 61< = R 62< = H, the synthesis method is as follows:1. Synthesis of intermediate 2a

[0029] Taking the compound 1a (80 mmol) in a 250 ml beaker, adding 120 ml THF, slowly adding potassium tert-butanol (80 mmol) in ice bath, reacting at room temperature for 1h, slowly adding various substituted ketones (40 mmol) in ice bath, heating to room temperature after adding, monitoring the reaction by TLC after 1h, adding water to quench the reaction after the reaction of the raw materials is completed, extracting by ethyl acetate, washing with water and saturated salt water for 3 times respectively, stirring by silica gel, and separating by column chromatography to obtain an oily compound, namely the intermediate 2 a.2. Synthesis of intermediate 3a

[0030] Dissolving the intermediate 2a (1 eq.) in chloroform, adding NBS (2 eq.) and p-toluenesulfonic acid (0.5 eq.) into the chloroform, heating the solution to reflux for about 2 hours, monitoring the reaction by TLC, stopping heating after the reaction is completed, cooling the solution to room temperature, adding water into the solution, extracting the solution by dichloromethane, washing with water and saturated salt water for 3 times respectively, drying and removing the solvent to obtain a brominated intermediate 3a without purification.3. Synthesis of intermediate 4a

[0031] The brominated intermediate 3a (1 eq.) is added to acetonitrile, followed by potassium carbonate(3 eq.), adding various substituted amines (2.2 eq.) under ice bath, reacting at room temperature for 24h after the addition is finished, monitoring the reaction by TLC, adding water to quench the reaction after the reaction is finished, extracting by ethyl acetate, washing with water and saturated salt water for 3 times respectively, drying and desolventizing to obtain an aminated intermediate 4a without purification.4. Synthesis of target product

[0032] The aminated intermediate 4a (1 eq.) is added to dichloromethane, followed by triethylamine (2 eq.), finally slowly adding pyrazole acyl chloride (1.5 eq.), monitoring the reaction by TLC, adding water to quench the reaction after the reaction is finished, extracting by dichloromethane, washing with water and saturated salt water for 3 times respectively, stirring a sample with silica gel, and performing column chromatography separation to obtain the product.

[0033] When R 61< = R 62< = F, Cl and Br, the synthesis method is as follows:1. Synthesis of intermediate 2a

[0034] Adding triphenylphosphine (4 eq.) and various substituted ketones (1 eq.) into a eggplant-shaped bottle with a proper size, adding a proper amount of DCM, slowly dropwise adding trichlorobromomethane (2 eq.) under ice bath, monitoring whether the reaction is finished or not after 30 min, adding water to quench the reaction if the reaction is finished, extracting by DCM, washing with water and saturated salt water for 2-3 times respectively, stirring with silica gel, and separating by column chromatography to obtain an oily compound, namely the intermediate 2 a.2. Synthesis of intermediate 3a

[0035] Dissolving the intermediate 2a (1 eq.) in chloroform, adding NBS (2 eq.) and p-toluenesulfonic acid (0.5 eq.) into the chloroform, heating the mixture to reflux for about 2 hours, monitoring whether the reaction is finished by TLC, stopping heating after the reaction is finished, cooling the mixture to room temperature, adding water into the mixture, extracting the mixture by dichloromethane, washing with water and saturated salt water for 2-3 times respectively, drying and removing the solvent to obtain a brominated intermediate 3a without purification.3. Synthesis of intermediate 4a

[0036] The brominated intermediate 3a (1 eq.) is added to acetonitrile, followed by potassium carbonate(3 eq.), adding various substituted amines (2.2 eq.) under ice bath, reacting at room temperature for 24h after the addition is finished, monitoring the reaction by TLC, adding water to quench the reaction after the reaction is finished, extracting by ethyl acetate, washing with water and saturated salt water for 2-3 times respectively, drying and desolventizing to obtain an aminated intermediate 4a without purification.4. Synthesis of target product

[0037] The aminated intermediate 4a (1 eq.) is added to dichloromethane, followed by triethylamine (2 eq.), finally slowly adding pyrazole acyl chloride (1.5 eq.), slowly adding the intermediate in ice bath if a large amount of the intermediate is reacted, adding a small amount of the intermediate at room temperature directly, monitoring whether the reaction is finished by TLC, adding water to quench the reaction after the reaction is finished, extracting by dichloromethane, washing the obtained product with water and saturated salt water for 2-3 times respectively, directly stirring the sample with silica gel if the reaction is finished in a small amount, carrying out column chromatography separation, and recrystallizing with ethanol and ethyl acetate if the reaction is finished in a large amount, wherein the product is a white solid.

[0038] The following illustratively provides a specific synthetic method for compound 1:

[0039] Adding triphenyl methyl phosphorus bromide (80 mmol, 2 eq.) into a 250 ml eggplant-shaped bottle, adding 120 ml THF, slowly adding potassium tert-butanol (80 mmol, 2 eq.) in ice bath, reacting at room temperature for 1h, then slowly adding 2, 4-dichloroacetophenone (40 mmol, 1 eq.) in ice bath, heating to room temperature after the addition is finished, monitoring the reaction by TLC after 1h, adding water to quench the reaction after the reaction of the raw materials is finished, extracting by ethyl acetate, washing with water and saturated salt water for 3 times respectively, drying and desolventizing to obtain a yellow oily compound, wherein the yellow oily compound contains a product and triphenylphosphine oxide, separating, directly stirring by silica gel, separating by column chromatography, and eluting by petroleum ether.

[0040] Dissolving 2, 4-dichlorostyrene (1 eq.) in chloroform , adding NBS (1.05 eq.), p-toluenesulfonic acid (0.3 eq.) into the chloroform, heating the solution to reflux for 2h at 70 °C, monitoring by TLC for reaction completion, stopping heating after the reaction is completed, cooling to room temperature, adding water, extracting by dichloromethane, washing with water and saturated salt for 2 times respectively, drying, and desolventizing to obtain a brominated intermediate without purification.

[0041] The brominated intermediate 3a (1 eq.) is added to acetonitrile, followed by potassium carbonate(3 eq.), then adding cyclopropylamine (2.2 eq.) under ice bath, reacting at room temperature for 24 hours after the addition is finished, monitoring by TLC, adding water for quenching reaction after the reaction is finished, extracting by ethyl acetate, washing by water and saturated salt for 3 times respectively, drying and desolventizing to obtain an aminated product without purification.

[0042] The aminated intermediate 4a (1 eq.) is added to dichloromethane, followed by triethylamine (2 eq.), finally slowly adding fluorine-containing pyrazole acyl chloride (1.5 eq.), monitoring by TLC, adding water to quench the reaction after the reaction is finished, extracting by dichloromethane, washing the dichloromethane with water and saturated salt water for 3 times respectively, directly stirring the sample with silica gel, and performing column chromatography separation (an eluent uses petroleum ether: ethyl acetate = 8: 1) to obtain a white solid product. Thus obtaining the compound 1.

[0043] The nuclear magnetic data of the target compounds of the present invention are listed in table 1. TABLE 1Compound numberNuclear magnetic data1 1< H NMR (600 MHz, DMSO-d 6 ) δ 7.61 (s, 1H), 7.40 (d, J = 8.3 Hz, 1H), 7.29 (s, 1H), 6.83 (t, J= 53.5 Hz, 1H), 5.43 (s, 1H), 5.18 (s, 1H), 4.37 (s, 2H), 3.73 (s, 3H), 2.73 - 2.55 (m, 1H), 0.83 - 0.61 (m, 2H), 0.59 - 0.42 (m, 2H).2 1< H NMR (500 MHz, CDCl3) δ 7.36 - 7.31 (m, 1H), 7.31 - 7.25 (m, 2H), 7.17 (t, J = 57.3 Hz, 1H), 5.30 (s, 1H), 5.25 (s, 1H), 4.40 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.54 (m, 2H).3 1< H NMR (500 MHz, CDCl3) δ 7.66 - 7.61 (m, 1H), 7.46 (dd, J = 4.8, 3.0 Hz, 1H), 7.37 - 7.30 (m, 2H), 7.17 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.16 (s, 1H), 4.39 (s, 2H), 3.96 (s, 3H), 3.74 - 3.63 (m, 1H), 0.76 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).4 1< H NMR (500 MHz, CDCl3) δ 7.26 (t, J = 57.3 Hz, 1H), 7.23 - 7.20 (m, 2H), 7.15 - 7.04 (m, 2H), 5.26 (s, 1H), 5.18 (s, 1H), 4.36 (s, 2H), 3.96 (s, 3H), 3.74 - 3.62 (m, 1H), 2.38 (s, 3H), 0.75 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).5 1< H NMR (500 MHz, CDCl3) δ 7.57 - 7.51 (m, 2H), 7.36 - 7.28 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).6 1< H NMR (500 MHz, CDCl3) δ 7.36 - 7.27 (m, 1H), 7.27 - 7.23 (m, 2H), 7.22 (t, J = 57.3 Hz, 1H), 7.18 - 7.11 (m, 1H), 5.24 (s, 1H), 5.17 (s, 1H), 4.31 (s, 2H), 3.96 (s, 3H), 3.74 - 3.59 (m, 1H), 2.35 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).7 1< H NMR (500 MHz, CDCl3) δ 7.46 (dd, J = 6.3, 1.6 Hz, 1H), 7.42 - 7.32 (m, 2H), 7.28 (ddd, J= 7.5, 6.4, 1.8 Hz, 1H), 7.17 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.72 - 3.64 (m, 1H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).8 1< H NMR (500 MHz, CDCl3) δ 7.40 (dd, J = 6.9, 2.7 Hz, 1H), 7.36 - 7.29 (m, 1H), 7.28 (s, 1H), 7.17 (t, J = 57.3 Hz, 1H), 5.28 (s, 1H), 5.24 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.73 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.54 (m, 2H).9 1< H NMR (500 MHz, CDCl3) δ 7.44 - 7.27 (m, 5H), 7.23 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.36 (s, 2H), 3.96 (s, 3H), 3.72 - 3.64 (m, 1H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).10 1< H NMR (500 MHz, CDCl3) δ 7.53 -7.40 (m, 2H), 7.24 (t, J = 57.3 Hz, 1H), 7.15 - 7.11 (m, 1H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.74 - 3.61 (m, 1H), 0.75 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).11 1< H NMR (500 MHz, CDCl3) δ 7.60 - 7.22 (m, 3H), 7.18 (t, J = 57.3 Hz, 1H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.73 - 3.62 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).12 1< H NMR (500 MHz, CDCl3) δ 7.24 (t, J = 57.3 Hz, 1H), 7.20 - 7.05 (m, 3H), 5.28 (s, 1H), 5.21 (s, 1H), 4.46 (s, 2H), 3.96 (s, 3H), 3.73 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).13 1< H NMR (500 MHz, CDC13) δ 7.56 (d, J = 4.9 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.02 (d, J = 8.1 Hz, 1H), 5.28 (s, 1H), 5.22 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).14 1< H NMR (500 MHz, CDC13) δ 7.41 - 7.35 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 5.28 (s, 1H), 5.24 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.71 - 3.65 (m, 1H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).15 1< H NMR (500 MHz, CDC13) δ 7.87 - 7.78 (m, 2H), 7.55 (d, J = 7.8 Hz, 2H), 7.23 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.36 (s, 2H), 3.96 (s, 3H), 3.73 - 3.62 (m, 1H), 3.18 (s, 3H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).16 1< H NMR (500 MHz, CDCl3) δ 7.41 - 7.35 (m, 3H), 7.35 - 7.30 (m, 1H), 7.21 (t, J = 57.3 Hz, 1H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).17 1< H NMR (500 MHz, CDCl3) δ 7.36 - 7.27 (m, 4H), 7.21 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.36 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).18 1< H NMR (500 MHz, CDC13) δ 7.41 - 7.33 (m, 3H), 7.22 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.16 (s, 1H), 4.42 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).19 1< H NMR (500 MHz, CDCl3) δ 7.25 (s, 2H), 7.17 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.16 (s, 1H), 4.42 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).20 1< H NMR (500 MHz, CDC13) δ 7.55 (ddd, J = 7.5, 5.0, 1.6 Hz, 1H), 7.45 -7.38 (m, 1H), 7.24 (t, J = 57.3 Hz, 1H), 7.18 - 7.09 (m, 2H), 5.23 (s, 1H), 5.19 (s, 1H), 4.38 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).21 1< H NMR (500 MHz, CDC13) δ 7.38 -7.34 (m, 1H), 7.24 (t, J = 57.3 Hz, 1H), 7.20 -7.07 (m, 3H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.72 - 3.62 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).22 1< H NMR (500 MHz, CDCl3) δ 7.44 (dd, J = 8.9, 5.0 Hz, 2H), 7.23 (t, J = 57.3 Hz, 1H), 7.05 (dd, J = 9.0, 8.0 Hz, 2H), 5.26 (s, 1H), 5.18 (s, 1H), 4.36 (s, 2H), 3.96 (s, 3H), 3.72 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).23 1< H NMR (500 MHz, CDCl3) δ 7.26 (t, J = 57.3 Hz, 1H), 7.23 - 7.10 (m, 1H), 6.88 - 6.79 (m, 2H), 5.25 (s, 1H), 5.18 (s, 1H), 4.38 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).24 1< H NMR (500 MHz, CDCl3) δ 7.20 (t, J = 57.3 Hz, 1H), 7.19 - 7.10 (m, 3H), 5.28 (s, 1H), 5.22 (s, 1H), 4.40 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).25 1< H NMR (500 MHz, CDCl3) δ 7.42 (tt, J = 7.9, 5.1 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.00 (td, J = 7.5, 0.9 Hz, 2H), 5.27 (s, 1H), 5.20 (s, 1H), 4.39 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).26 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 6.67 (ddd, J = 8.3, 7.4, 0.9 Hz, 2H), 5.27 (s, 1H), 5.20 (s, 1H), 4.39 (s, 2H), 3.96 (s, 3H), 3.72 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).27 1< H NMR (500 MHz, CDC13) δ 7.51 - 7.42 (m, 4H), 7.23 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.36 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).28 1< H NMR (500 MHz, CDCl3) δ 7.66 (d, J = 1.9 Hz, 1H), 7.44 (dd, J = 9.2, 1.9 Hz, 1H), 7.32 (d, J = 28.5 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.16 (s, 1H), 4.39 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).29 1< H NMR (500 MHz, CDCl3) δ 7.59 - 7.48 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 5.25 (s, 1H), 5.20 (s, 1H), 4.39 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).30 1< H NMR (500 MHz, CDCl3) δ 7.49 (d, J = 8.1 Hz, 2H), 7.23 (t, J = 57.3 Hz, 1H), 7.08 (t, J = 8.2 Hz, 1H), 5.28 (s, 1H), 5.20 (s, 1H), 4.17 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).31 1< H NMR (500 MHz, CDCl3) δ 7.62 (s, 2H), 7.23 (t, J = 57.3 Hz, 1H), 5.29 (s, 1H), 5.20 (s, 1H), 4.17 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).32 1< H NMR (500 MHz, CDC13) δ 7.36 - 7.26 (m, 1H), 7.25 (t, J = 57.3 Hz, 1H), 7.18 - 7.11 (m, 3H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s,2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 2.38 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).33 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 7.09 - 6.91 (m, 3H), 5.24 (s, 1H), 5.17 (s, 1H), 4.31 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 2.28 (d, J = 1.0 Hz, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).34 1< H NMR (500 MHz, CDC13) δ 7.23 (t, J = 57.3 Hz, 1H), 7.11 - 7.07 (m, 1H), 7.07 - 7.00 (m, 2H), 5.27 (s, 1H), 5.23 (s, 1H), 4.33 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 2.37 (s, 3H), 2.34 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).35 1< H NMR (500 MHz, CDCl3) δ 7.24 (t, J = 57.3 Hz, 1H), 7.12 - 7.00 (m, 3H), 5.21 (s, 1H), 5.19 (s, 1H), 4.29 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 2.27 (s, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).36 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 6.80 (s, 2H), 5.21 (s, 1H), 5.19 (s, 1H), 4.29 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 2.26 (d, J = 0.9 Hz, 9H), 0.74 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).37 1< H NMR (500 MHz, CDC13) δ 7.22 (t, J = 57.3 Hz, 1H), 7.15 - 7.05 (m, 3H), 5.27 (s, 1H), 5.23 (s, 1H), 4.33 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 3.08 - 2.99 (m, 1H), 2.34 (s, 3H), 1.27 (d, J = 6.6 Hz, 6H), 0.75 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).38 1< H NMR (500 MHz, CDCl3) δ 7.26 (t, J = 57.3 Hz, 1H), 7.20 - 7.10 (m, 2H), 6.97 - 6.93 (m, 1H), 5.26 (s, 1H), 5.19 (s, 1H), 4.35 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 3.32 - 3.22 (m, 1H), 2.37 (s, 3H), 1.26 (d, J = 6.8 Hz, 6H), 0.75 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).39 1< H NMR (500 MHz, CDC13) δ 7.23 (t, J = 57.3 Hz, 1H), 7.11 - 6.92 (m, 3H), 5.27 (s, 1H), 5.21 (s, 1H), 4.35 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 2.37 (s, 3H), 1.34 (s, 9H), 0.75 - 0.64 (m, 2H), 0.64 - 0.55 (m, 2H).40 1< H NMR (500 MHz, CDCl3) δ 7.26 (t, J = 57.3 Hz, 1H), 7.23 - 7.04 (m, 3H), 5.27 (s, 1H), 5.23 (s, 1H), 4.34 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 2.34 (s, 3H), 1.33 (s, 9H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).41 1< H NMR (500 MHz, CDCl3) δ 7.25 (t, J = 57.3 Hz, 1H), 7.18 - 7.06 (m, 3H), 5.24 (s, 1H), 5.17 (s, 1H), 4.31 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 2.94 - 2.86 (m, 1H), 2.34 (s, 3H), 1.27 (d, J = 6.6 Hz, 6H), 0.78 - 0.65 (m, 2H), 0.65 - 0.54 (m, 2H).42 1< H NMR (500 MHz, CDCl3) δ 7.37 - 7.31 (m, 1H), 7.24 (dd, J = 8.0, 1.9 Hz, 1H), 7.21 (t, J= 57.3 Hz, 1H), 7.18 - 7.11 (m, 1H), 5.23 (s, 1H), 5.19 (s, 1H), 4.38 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).43 1< H NMR (500 MHz, CDCl3) δ 7.36 - 7.23 (m, 2H), 7.17 (t, J = 57.3 Hz, 1H), 7.01 (ddd, J = 9.1, 8.1, 1.8 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.15 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).44 1< H NMR (500 MHz, CDC13) δ 7.39 -7.32 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 7.14 - 7.09 (m, 1H), 5.27 (s, 1H), 5.22 (s, 1H), 4.40 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.53 (m, 2H).45 1< H NMR (500 MHz, CDC13) δ 7.55 - 7.48 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 5.28 (s, 1H), 5.24 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.75 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).46 1< H NMR (500 MHz, CDCl3) δ 7.52 (dd, J = 10.6, 1.1 Hz, 1H), 7.36 -7.33 (m, 1H), 7.24 (t,J = 57.3 Hz, 1H), 7.17 - 7.10 (m, 1H), 5.28 (s, 1H), 5.24 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).47 1< H NMR (500 MHz, CDCl3) δ 7.70 - 7.42 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.73 - 3.63 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).48 1< H NMR (500 MHz, CDC13) δ 7.81 (d, J = 2.0 Hz, 1H), 7.71 (dd, J = 7.8, 1.9 Hz, 1H), 7.51 (d, J = 7.8 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.73 - 3.63 (m, 1H), 3.21 (s, 3H), 0.75 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).49 1< H NMR (500 MHz, CDCl3) δ 7.80 - 7.71 (m, 2H), 7.54 - 7.44 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.71 - 3.63 (m, 1H), 3.18 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).50 1< H NMR (500 MHz, CDCl3) δ 7.93 (dd, J = 8.2, 1.8 Hz, 1H), 7.60 (dd, J = 6.3, 1.8 Hz, 1H), 7.50 - 7.38 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 5.31 (s, 1H), 5.25 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.73 - 3.63 (m, 1H), 3.20 (s, 3H), 0.75 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).51 1< H NMR (500 MHz, CDC13) δ 7.95 - 7.50 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 5.29 (s, 1H), 5.22 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 3.18 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).52 1< H NMR (500 MHz, CDCl3) δ 7.82 - 7.76 (m, 2H), 7.58 - 7.52 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.36 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 3.27 (q, J = 9.2 Hz, 2H), 1.27 (t, J = 9.2 Hz, 3H), 0.76 - 0.65 (m, 2H), 0.65 - 0.54 (m, 2H).53 1< H NMR (500 MHz, CDC13) δ 7.97 (t, J = 1.4 Hz, 1H), 7.80 - 7.73 (m, 1H), 7.55 - 7.46 (m, 2H), 7.23 (t, J= 57.3 Hz, 1H), 5.30 (s, 1H), 5.20 (s, 1H), 4.37 (s, 2H), 3.96 (s, 3H), 3.73 - 3.63 (m, 1H), 3.28 (q, J = 9.1 Hz, 2H), 1.26 (t, J = 9.1 Hz, 3H), 0.75 - 0.65 (m, 2H), 0.65 - 0.53 (m, 2H).54 1< H NMR (500 MHz, CDCl3) δ 7.53 (d, J = 1.9 Hz, 1H), 7.38 -7.31 (m, 2H), 7.24 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.18 (s, 1H), 4.18 (s, 2H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 2.99 - 2.90 (m, 1H), 1.23 (s, 2H), 1.18 (s, 2H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).55 1< H NMR (500 MHz, CDCl3) δ 7.43 (dd, J = 7.6, 4.9 Hz, 1H), 7.36 - 7.30 (m, 1H), 7.25 (t, J = 57.3 Hz, 1H), 7.23 - 7.09 (m, 1H), 5.23 (s, 1H), 5.19 (s, 1H), 4.38 (s, 2H), 3.96 (s, 3H), 3.72 - 3.63 (m, 1H), 2.99 - 2.90 (m, 1H), 1.31 - 1.21 (m, 2H), 1.21 - 1.12 (m, 2H), 0.78 - 0.65 (m, 2H), 0.65 - 0.51 (m, 2H).56 1< H NMR (500 MHz, CDCl3) δ 7.36 (ddd, J = 7.9, 6.5, 4.9 Hz, 1H), 7.20 (t, J = 57.3 Hz, 1H), 7.16 - 7.09 (m, 1H), 7.06 - 6.98 (m, 2H), 5.24 (s, 1H), 5.19 (s, 1H), 4.86 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.76 (p, J = 5.7 Hz, 1H), 1.24 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).57 1< H NMR (500 MHz, CDCl3) δ 7.40 - 7.31 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 7.17 - 7.09 (m, 1H), 5.23 (s, 1H), 5.19 (s, 1H), 4.86 (q, J = 7.5, 1.0 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.73 (m, 1H), 1.24 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.65 (m, 2H).58 1< H NMR (500 MHz, CDC13) δ 7.41 (ddd, J = 8.7, 7.4, 5.0 Hz, 2H), 7.23 (t, J = 57.3 Hz, 1H), 7.18 - 7.08 (m, 2H), 5.23 (s, 1H), 5.15 (s, 1H), 4.82 (q, J= 7.5, 1.1 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).59 1< H NMR (500 MHz, CDCl3) δ 7.33 - 7.28 (m, 2H), 7.19 (t, J = 57.3 Hz, 1H), 6.90 (d, J = 1.3 Hz, 1H), 6.89 (d, J = 1.3 Hz, 1H), 5.26 (s, 1H), 5.17 (s, 1H), 4.81 (q, J = 7.7, 1.1 Hz, 1H), 3.96 (s, 3H), 3.81 - 3.72 (m, 1H), 1.23 (d, J = 7.5 Hz, 3H), 0.80 - 0.72 (m, 2H), 0.72 - 0.64 (m, 2H).60 1< H NMR (500 MHz, CDCl3) δ 7.22 (t, J = 57.3 Hz, 1H), 7.11 - 7.02 (m, 4H), 5.26 (s, 1H), 5.17 (s, 1H), 4.81 (q, J = 7.7, 1.1 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.72 (m, 1H), 2.38 (s, 3H), 1.23 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).61 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.29 (m, 2H), 7.20 (t, J = 59.5 Hz, 1H), 6.87 (d, J = 1.4 Hz, 1H), 6.85 (d, J = 1.3 Hz, 1H), 5.26 (s, 1H), 5.17 (s, 1H), 4.81 (q, J = 7.7, 1.1 Hz, 1H), 3.96 (s, 3H), 3.82 (s, 3H), 3.80 - 3.71 (m, 1H), 1.23 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).62 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 7.18 - 7.08 (m, 2H), 7.01 (ddd, J = 9.8, 5.0, 2.2 Hz, 1H), 5.24 (s, 1H), 5.19 (s, 1H), 4.86 (q, J = 7.6, 0.9 Hz, 1H), 3.96 (s, 3H), 3.81 - 3.72 (m, 1H), 1.24 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).63 1< H NMR (500 MHz, CDC13) δ 7.21 (t, J = 57.3 Hz, 1H), 6.94 - 6.86 (m, 3H), 5.29 (s, 1H), 5.22 (s, 1H), 4.23 (q, J= 7.7, 1.1 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 1.24 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).64 1< H NMR (500 MHz, CDC13) δ 7.19 (t, J = 57.3 Hz, 1H), 7.10 - 7.07 (m, 1H), 6.91 (td, J = 8.3, 2.7 Hz, 1H), 6.83 (td, J = 8.0, 2.7 Hz, 1H), 5.23 (s, 1H), 5.16 (s, 1H), 4.82 (q, J = 7.5, 1.1 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.70 (m, 1H), 1.25 (d, J= 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).65 1< H NMR (500 MHz, CDCl3) δ 7.47 - 7.41 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 7.07 (dd, J = 8.9, 2.3 Hz, 1H), 5.24 (s, 1H), 5.19 (s, 1H), 4.86 (q, J = 7.5, 1.0 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.73 (m, 1H), 1.24 (d, J = 7.7 Hz, 3H), 0.79 - 0.72 (m, 2H), 0.72 - 0.65 (m, 2H).66 1< H NMR (500 MHz, CDCl3) δ 7.52 -7.46 (m, 2H), 7.36 -7.33 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.17 (s, 1H), 4.81 (q, J = 7.7, 1.1 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.23 (d, J = 7.5 Hz, 3H), 0.79 - 0.72 (m, 2H), 0.72 - 0.65 (m, 2H).67 1< H NMR (500 MHz, CDC13) δ 7.41 (d, J = 2.1 Hz, 1H), 7.34 - 7.24 (m, 1H), 7.21 (t, J = 57.3 Hz, 1H), 7.14 (d, J = 47.5 Hz, 1H), 5.21 (s, 1H), 5.15 (s, 1H), 4.87 (q, J = 7.7, 1.0 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).68 1< H NMR (500 MHz, CDC13) δ 7.36 - 7.28 (m, 2H), 7.20 (t, J = 57.3 Hz, 1H), 7.06 - 7.00 (m, 2H), 5.26 (s, 1H), 5.18 (s, 1H), 4.81 (q, J = 7.7, 1.1 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.72 (m, 1H), 1.23 (d, J = 7.5 Hz, 3H), 0.79 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).69 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.22 (m, 1H), 7.17 (t, J = 57.3 Hz, 1H), 6.98 - 6.91 (m, 2H), 6.79 (dd, J = 2.6, 1.9 Hz, 1H), 5.24 (s, 1H), 5.19 (s, 1H), 4.86 (q, J = 7.5, 1.0 Hz, 1H), 3.96 (s, 3H), 3.82 (s, 3H), 3.80 - 3.73 (m, 1H), 1.24 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).70 1< H NMR (500 MHz, CDCl3) δ 7.27 (t, J = 57.3 Hz, 1H), 7.18 - 7.00 (m, 4H), 5.23 (s, 1H), 5.19 (s, 1H), 4.86 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 2.38 (s, 3H), 1.23 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).71 1< H NMR (500 MHz, CDCl3) δ 7.69 - 7.58 (m, 2H), 7.36 - 7.32 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.17 (s, 1H), 4.79 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.73 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.65 (m, 2H).72 1< H NMR (500 MHz, CDCl3) δ 7.44 - 7.27 (m, 4H), 7.21 (t, J = 57.3 Hz, 1H), 5.21 (s, 1H), 5.15 (s, 1H), 4.87 (q, J = 7.7, 1.0 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).73 1< H NMR (500 MHz, CDC13) δ 7.41 - 7.33 (m, 3H), 7.15 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.20 (s, 1H), 4.28 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).74 1< H NMR (500 MHz, CDC13) δ 7.29 (s, 2H), 7.15 (t, J = 57.3 Hz, 1H), 5.22 (s, 1H), 5.19 (s, 1H), 4.28 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.79 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).75 1< H NMR (500 MHz, CDC13) δ 7.42 - 7.32 (m, 2H), 7.24 (t, J = 57.3 Hz, 1H), 7.18 - 7.08 (m, 1H), 5.30 (s, 1H), 5.23 (s, 1H), 4.34 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).76 1< H NMR (500 MHz, CDC13) δ 7.50 (d, J = 2.3 Hz, 1H), 7.41 - 7.34 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 5.31 (s, 1H), 5.24 (s, 1H), 4.34 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.71 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).77 1< H NMR (500 MHz, CDC13) δ 7.34 - 7.29 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.19 - 7.09 (m, 2H), 5.23 (s, 1H), 5.19 (s, 1H), 4.88 (q, J = 7.7, 1.0 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).78 1< H NMR (500 MHz, CDC13) δ 7.42 (tt, J = 7.9, 5.1 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 7.04 - 6.98 (m, 2H), 5.28 (s, 1H), 5.23 (s, 1H), 4.83 (q, J= 7.5, 1.1 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).79 1< H NMR (500 MHz, CDCl3) δ 7.21 (t, J = 57.3 Hz, 1H), 6.67 (ddd, J = 8.3, 7.4, 1.0 Hz, 2H), 5.28 (s, 1H), 5.23 (s, 1H), 4.83 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).80 1< H NMR (500 MHz, CDCl3) δ 7.67 - 7.61 (m, 1H), 7.44 - 7.30 (m, 3H), 7.15 (t, J = 57.3 Hz, 1H), 5.19 (s, 1H), 5.11 (s, 1H), 4.83 (q, J= 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.65 (m, 2H).81 1< H NMR (500 MHz, CDCl3) δ 7.54 (dt, J = 7.9, 1.6 Hz, 1H), 7.42 (t, J = 1.9 Hz, 1H), 7.29 (dd, J = 8.0, 6.8 Hz, 1H), 7.27 - 7.21 (m, 1H), 7.21 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.19 (s, 1H), 4.90 - 4.82 (m, 1H), 3.96 (s, 2H), 3.80 - 3.72 (m, 1H), 1.24 (d, J = 7.7 Hz, 3H), 0.79 - 0.66 (m, 4H).82 1< H NMR (500 MHz, CDC13) δ 7.71 (d, J = 1.9 Hz, 1H), 7.47 (dd, J = 9.0, 2.0 Hz, 1H), 7.34 - 7.23 (m, 1H), 7.15 (t, J = 57.3 Hz, 1H), 5.18 (s, 1H), 5.09 (s, 1H), 4.83 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.71 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).83 1< H NMR (500 MHz, CDCl3) δ 7.65 - 7.58 (m, 2H), 7.51 (dd, J = 7.9, 2.6 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 5.24 (s, 1H), 5.18 (s, 1H), 4.88 (d, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).84 1< H NMR (500 MHz, CDC13) δ 7.52 (d, J = 8.3 Hz, 2H), 7.21 (t, J = 57.3 Hz, 1H), 7.07 (d, J = 8.1 Hz, 1H), 5.23 (s, 1H), 5.22 (s, 1H), 4.82 (q, J = 7.6, 1.1 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).85 1< H NMR (500 MHz, CDCl3) δ 7.68 (s, 2H), 7.21 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.22 (s, 1H), 4.82 (d, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).86 1< H NMR (500 MHz, CDCl3) δ 7.60 (dd, J = 7.9, 1.5 Hz, 1H), 7.36 - 7.30 (m, 1H), 7.24 (t, J = 57.3 Hz, 1H), 7.19 -7.10 (m, 1H), 5.25 (s, 1H), 5.20 (s, 1H), 4.39 (s, 1H), 4.14 (s, 1H), 3.96 (s, 3H), 3.71 - 3.64 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).87 1< H NMR (500 MHz, CDCl3) δ 7.33 - 7.26 (m, 1H), 7.26 - 7.21 (m, 1H), 7.19 (t, J = 57.3 Hz, 1H), 7.17 - 7.09 (m, 2H), 5.22 (s, 1H), 5.14 (s, 1H), 4.74 (d, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 2.35 (s, 3H), 1.24 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).88 1< H NMR (500 MHz, CDCl3) δ 7.21 (t, J = 57.3 Hz, 1H), 7.00 - 6.89 (m, 3H), 5.22 (s, 1H), 5.14 (s, 1H), 4.74 (d, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 2.29 (s, 3H), 2.28 (s, 3H), 1.24 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).89 1< H NMR (500 MHz, CDCl3) δ 7.27 (t, J = 57.3 Hz, 1H), 7.10 -7.01 (m, 3H), 5.26 (s, 1H), 5.18 (s, 1H), 4.79 (d, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.73 (m, 1H), 2.37 (d, J = 0.9 Hz, 6H), 1.24 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).90 1< H NMR (500 MHz, CDCl3) δ 7.22 (t, J = 57.3 Hz, 1H), 7.12 - 6.98 (m, 3H), 5.03 (s, 1H), 5.03 (s, 1H), 4.64 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 2.29 (s, 6H), 1.25 (d, J = 7.6 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).91 1< H NMR (500 MHz, CDCl3) δ 7.21 (t, J = 57.3 Hz, 1H), 6.78 (s, 2H), 5.03 (s, 1H), 5.03 (s, 1H), 4.64 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 2.26 (s, 3H), 2.25 (s, 6H), 1.25 (d, J = 7.6 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).92 1< H NMR (500 MHz, CDCl3) δ 7.20 (t, J = 57.3 Hz, 1H), 7.16 - 7.08 (m, 3H), 5.26 (s, 1H), 5.18 (s, 1H), 4.79 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.73 (m, 1H), 3.08 - 2.99 (m, 1H), 2.37 (s, 3H), 1.30 (d, J = 6.6 Hz, 3H), 1.25 (d, J = 1.1 Hz, 3H), 1.24 (d, J = 2.0 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.64 (m, 2H).93(500 MHz, CDCl3) δ 7.25 (t, J = 57.3 Hz, 1H), 7.21 - 6.93 (m, 3H), 5.26 (s, 1H), 5.17 (s, 1H), 4.78 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 3.26 - 3.16 (m, 1H), 2.37 (s, 3H), 1.28 (d, J = 6.9 Hz, 3H), 1.25 (d, J= 5.9 Hz, 3H), 1.23 (d, J = 5.2 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).94 1< H NMR (500 MHz, CDCl3) δ 7.21 (t, J = 57.3 Hz, 1H), 7.08 (d, J = 7.5 Hz, 1H), 6.97 - 6.86 (m, 2H), 5.26 (s, 1H), 5.20 (s, 1H), 4.83 (q, J= 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 2.37 (s, 3H), 1.34 (s, 9H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).95 1< H NMR (500 MHz, CDC13) δ 7.34 - 7.22 (m, 1H), 7.18 (t, J = 57.3 Hz, 1H), 7.07 - 7.00 (m, 2H), 5.26 (s, 1H), 5.18 (s, 1H), 4.79 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.73 (m, 1H), 2.37 (s, 3H), 1.33 (s, 9H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.64 (m, 2H).96 1< H NMR (500 MHz, CDCl3) δ 7.21 (t, J = 57.3 Hz, 1H), 7.08 (dt, J = 2.7, 1.2 Hz, 3H), 5.22 (s, 1H), 5.14 (s, 1H), 4.74 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.71 (m, 1H), 2.95 - 2.86 (m, 1H), 2.35 (s, 3H), 1.30 (d, J = 6.6 Hz, 3H), 1.25 (s, 3H), 1.24 (d, J = 0.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).97 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.20 (m, 3H), 7.18 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.15 (s, 1H), 4.82 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.81 - 3.69 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).98 1< H NMR (500 MHz, CDCl3) δ 7.27 (t, J = 57.3 Hz, 1H), 7.24 - 7.09 (m, 2H), 7.05 (ddd, J = 9.0, 8.1, 1.8 Hz, 1H), 5.23 (s, 1H), 5.15 (s, 1H), 4.87 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).99 1< H NMR (500 MHz, CDCl3) δ 7.49 (dd, J = 5.1, 2.5 Hz, 1H), 7.35 (ddd, J = 7.3, 4.9, 2.4 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.15 - 7.07 (m, 1H), 5.23 (s, 1H), 5.19 (s, 1H), 4.87 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 0.79 - 0.72 (m, 2H), 0.72 - 0.65 (m, 2H).100 1< H NMR (500 MHz, CDCl3) δ 7.65 - 7.43 (m, 3H), 7.21 (t, J = 57.3 Hz, 1H), 5.31 (s, 1H), 5.23 (s, 1H), 4.34 (q, J = 7.5 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.71 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).101 1< H NMR (500 MHz, CDCl3) δ 7.52 (dd, J = 10.6, 1.3 Hz, 1H), 7.36 - 7.28 (m, 1H), 7.21 (t, J= 57.3 Hz, 1H), 7.20 - 7.07 (m, 1H), 5.32 (s, 1H), 5.24 (s, 1H), 4.34 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).102 1< H NMR (500 MHz, CDCl3) δ 7.71 -7.55 (m, 2H), 7.36 (d, J = 11.6 Hz, 1H), 7.21 (q, J = 57.3 Hz, 1H), 5.21 (s, 1H), 5.15 (s, 1H), 4.87 (q, J= 7.7, 1.0 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).103 1< H NMR (500 MHz, CDCl3) δ 7.75 (d, J = 1.9 Hz, 1H), 7.70 (dd, J = 8.1, 2.0 Hz, 1H), 7.57 (d, J = 8.1 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 5.21 (s, 1H), 5.15 (s, 1H), 4.87 (q, J = 7.7, 1.0 Hz, 1H), 3.96 (s, 3H), 3.75 (p, J = 5.8 Hz, 1H), 3.21 (s, 3H), 1.24 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).104 1< H NMR (500 MHz, CDCl3) δ 7.75 (ddd, J = 8.6, 2.0, 1.2 Hz, 1H), 7.51 (t, J = 2.0 Hz, 1H), 7.48 (dd, J = 8.5, 6.7 Hz, 1H), 7.35 - 7.07 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 5.24 (s, 1H), 5.19 (s, 1H), 4.86 (q, J= 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.72 (m, 1H), 3.18 (s, 3H), 1.24 (d, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).105 1< H NMR (500 MHz, CDCl3) δ 7.92 (dd, J = 8.2, 1.9 Hz, 1H), 7.63 (dd, J= 6.5, 1.8 Hz, 1H), 7.49 - 7.40 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.20 (s, 1H), 4.89 (q, J = 7.5, 1.0 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.71 (m, 1H), 3.20 (s, 3H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).106 1< H NMR (500 MHz, CDCl3) δ 7.70 - 7.60 (m, 2H), 7.56 (d, J = 9.3 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 5.31 (s, 1H), 5.24 (s, 1H), 4.34 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.72 (m, 1H), 3.18 (s, 3H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).107 1< H NMR (500 MHz, CDCl3) δ 7.84 - 7.74 (m, 2H), 7.51 - 7.43 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 5.26 (s, 1H), 5.17 (s, 1H), 4.81 (q, J = 7.7, 1.1 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.73 (m, 1H), 3.27 (q, J = 9.2, 1.4 Hz, 2H), 1.27 (t, J = 9.2 Hz, 3H), 1.23 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).108 1< H NMR (500 MHz, CDCl3) δ 7.77 (ddd, J = 8.4, 1.8, 1.1 Hz, 1H), 7.66 -7.46 (m, 2H), 7.35 - 7.31 (m, 1H), 7.21 (t, J = 57.3 Hz, 1H), 5.24 (s, 1H), 5.19 (s, 1H), 4.86 (q, J = 7.5, 0.9 Hz, 1H), 3.96 (s, 3H), 3.80 - 3.72 (m, 1H), 3.28 (q, J = 9.2, 2.6 Hz, 2H), 1.26 (t, J = 9.2 Hz, 3H), 1.24 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).109 1< H NMR (500 MHz, CDCl3) δ 7.51 (d, J = 1.5 Hz, 1H), 7.36 - 7.32 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 5.21 (s, 1H), 5.15 (s, 1H), 4.87 (q, J = 7.7, 1.0 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.71 (m, 1H), 2.98 - 2.90 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 1.24 - 1.20 (m, 2H), 1.20 - 1.13 (m, 2H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).110 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.21 (m, 3H), 7.18 (t, J = 57.3 Hz, 1H), 5.23 (s, 1H), 5.16 (s, 1H), 4.82 (q, J = 7.5, 1.1 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.72 (m, 1H), 2.99 - 2.91 (m, 1H), 1.25 (d, J = 7.5 Hz, 3H), 1.24 - 1.20 (m, 2H), 1.20 - 1.13 (m, 2H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).111 1< H NMR (500 MHz, CDCl3) δ 7.49 - 7.45 (m, 2H), 7.42 - 7.37 (m, 1H), 7.35 - 7.30 (m, 2H), 7.25 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).112 1< H NMR (500 MHz, CDC13) δ 7.57 - 7.52 (m, 2H), 7.36 - 7.28 (m, 2H), 7.21 (t, J= 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 0.75 - 0.65 (m, 2H), 0.65 - 0.53 (m, 2H).113 1< H NMR (500 MHz, CDC13) δ 7.59 -7.51 (m, 2H), 7.38 -7.28 (m, 2H), 7.20 (t, J = 57.3 Hz, 1H), 4.69 (s, 2H), 4.02 (s, 3H), 3.64 - 3.58 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).116 1< H NMR (500 MHz, CDC13) δ 7.49 (dd, J = 7.9, 1.6 Hz, 1H), 7.42 -7.35 (m, 2H), 7.35 - 7.25 (m, 1H), 7.21 (q, J = 57.3 Hz, 1H), 4.62 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.54 (m, 2H).117 1< H NMR (500 MHz, CDC13) δ 7.45 (t, J = 1.9 Hz, 1H), 7.42 -7.34 (m, 3H), 7.22 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).118 1< H NMR (500 MHz, CDC13) δ 7.43 - 7.38 (m, 2H), 7.27 (t, J = 57.3 Hz, 1H), 7.23 - 7.09 (m, 1H), 4.62 (s, 2H), 3.96 (s, 3H), 3.63 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).119 1< H NMR (500 MHz, CDCl3) δ 7.45 -7.35 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).120 1< H NMR (500 MHz, CDCl3) δ 7.42 - 7.32 (m, 3H), 7.22 (t, J= 57.3 Hz, 1H), 4.65 (s, 2H), 3.96 (s, 3H), 3.62 - 3.54 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).121 1< H NMR (500 MHz, CDCl3) δ 7.52 - 7.41 (m, 3H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).122 1< H NMR (500 MHz, CDCl3) δ 7.43 - 7.31 (m, 3H), 7.17 (t, J = 57.3 Hz, 1H), 4.76 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.75 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).123 1< H NMR (500 MHz, CDCl3) δ 7.29 (t, J = 7.4 Hz, 2H), 7.17 (d, J = 57.3 Hz, 1H), 4.65 (s, 2H), 3.96 (s, 3H), 3.62 - 3.54 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).124 1< H NMR (500 MHz, CDCl3) δ 7.36 - 7.31 (m, 2H), 7.31 - 7.24 (m, 1H), 7.19 (q, J= 7.4 Hz, 1H), 7.16 - 7.10 (m, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).125 1< H NMR (500 MHz, CDCl3) δ 7.34 -7.30 (m, 2H), 7.25 (ddd, J = 8.1, 2.5, 1.3 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.18 - 7.13 (m, 1H), 4.68 (s, 2H), 3.64 - 3.58 (m, 1H), 0.73 - 0.65 (m, 2H), 0.64 - 0.57 (m, 2H).126 1< H NMR (500 MHz, CDC13) δ 7.36 - 7.28 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 6.88 - 6.78 (m, 2H), 4.65 (s, 2H), 3.96 (s, 3H), 3.61 - 3.54 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).127 1< H NMR (500 MHz, CDC13) δ 7.36 - 7.24 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.20 - 7.11 (m, 2H), 4.69 (s, 2H), 3.96 (s, 3H), 3.62 - 3.54 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).128 1< H NMR (500 MHz, CDCl3) δ 7.43 (tt, J = 7.8, 4.9 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 6.98 (td, J = 7.5, 0.9 Hz, 2H), 4.66 (s, 2H), 3.96 (s, 3H), 3.62 - 3.54 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).129 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 6.73 (tt, J = 8.2, 0.9 Hz, 2H), 4.67 (s, 2H), 3.96 (s, 3H), 3.62 - 3.54 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).130 1< H NMR (500 MHz, CDC13) δ 7.35 -7.30 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.19 - 7.09 (m, 2H), 4.68 (s, 2H), 3.96 (s, 3H), 3.63 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).131 1< H NMR (500 MHz, CDCl3) δ 7.46 (s, 4H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).132 1< H NMR (500 MHz, CDC13) δ 7.64 - 7.56 (m, 1H), 7.56 - 7.50 (m, 1H), 7.36 - 7.30 (m, 2H), 7.22 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.54 (m, 2H).133 1< H NMR (500 MHz, CDCl3) δ 7.57 - 7.51 (m, 2H), 7.46 (ddd, J = 8.1, 2.0, 1.3 Hz, 1H), 7.36 - 7.28 (m, 1H), 7.21 (t, J= 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).134 1< H NMR (500 MHz, CDC13) δ 7.69 (d, J = 1.9 Hz, 1H), 7.45 -7.35 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.54 (m, 2H).135 1< H NMR (500 MHz, CDCl3) δ 7.60 (d, J = 7.7 Hz, 1H), 7.55 -7.48 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 4.68 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).136 1< H NMR (500 MHz, CDCl3) δ 7.49 (d, J = 8.1 Hz, 2H), 7.23 (t, J = 57.3 Hz, 1H), 7.08 (t, J = 8.1 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.63 - 3.55 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).137 1< H NMR (500 MHz, CDCl3) δ 7.62 (s, 2H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.63 - 3.55 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).138 1< H NMR (500 MHz, CDCl3) δ 7.60 - 7.53 (m, 2H), 7.37 (dd, J = 8.8, 1.8 Hz, 1H), 7.23 (t, J= 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.63 - 3.56 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).139 1< H NMR (500 MHz, CDC13) δ 7.39 (dt, J = 7.0, 2.0 Hz, 1H), 7.25 (s, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.20 - 7.13 (m, 2H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 2.38 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).140 1< H NMR (500 MHz, CDCl3) δ 7.29 (t, J = 57.3 Hz, 1H), 7.14 - 7.10 (m, 1H), 6.98 - 6.89 (m, 2H), 4.60 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 2.28 (s, 3H), 2.27 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).141 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 7.11 - 7.03 (m, 3H), 4.64 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 2.37 (s, 3H), 2.35 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).142 1< H NMR (500 MHz, CDCl3) δ 7.24 (t, J = 57.3 Hz, 1H), 7.13 - 7.10 (m, 1H), 7.03 - 6.99 (m, 2H), 4.58 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 2.26 (s, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).143 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 6.82 (s, 2H), 4.58 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 2.27 (s, 3H), 2.26 (s, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).144 1< H NMR (500 MHz, CDCl3) δ 7.22 (t, J = 57.3 Hz, 1H), 7.16 - 7.09 (m, 3H), 4.64 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 3.08 - 2.99 (m, 1H), 2.35 (s, 3H), 1.27 (d, J = 6.6 Hz, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).145 1< H NMR (500 MHz, CDCl3) δ 7.27 (t, J = 57.3 Hz, 1H), 7.22 - 7.10 (m, 2H), 7.00 - 6.95 (m, 1H), 4.65 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 3.34 - 3.23 (m, 1H), 2.37 (s, 3H), 1.26 (d, J = 6.8 Hz, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).146 1< H NMR (500 MHz, CDC13) δ 7.24 (t, J = 57.3 Hz, 1H), 7.12 (d, J = 1.9 Hz, 1H), 7.01-6.94 (m, 2H), 4.65 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 2.37 (s, 3H), 1.34 (s, 9H), 0.72 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).147 1< H NMR (500 MHz, CDC13) δ 7.28 (t, J = 57.3 Hz, 1H), 7.25 - 7.11 (m, 2H), 7.06 (dq, J = 7.3, 1.0 Hz, 1H), 4.64 (s, 2H), 3.96 (s, 3H), 3.63 - 3.57 (m, 1H), 2.35 (s, 3H), 1.33 (s, 9H), 0.73 - 0.65 (m, 2H), 0.65 - 0.57 (m, 2H).148 1< H NMR (500 MHz, CDC13) δ 7.27 (t, J = 57.3 Hz, 1H), 7.16 (d, J = 44.5 Hz, 1H), 7.12 - 7.05 (m, 2H), 4.60 (s, 2H), 3.96 (s, 3H), 3.63 - 3.57 (m, 1H), 2.95 - 2.85 (m, 1H), 2.37 (s, 3H), 1.27 (d, J = 6.6 Hz, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).149 1< H NMR (500 MHz, CDCl3) δ 7.36 - 7.31 (m, 1H), 7.27 (td, J = 7.6, 1.9 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.22 - 7.01 (m, 2H), 4.60 (s, 2H), 3.96 (s, 3H), 3.63 - 3.57 (m, 1H), 2.36 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).150 1< H NMR (500 MHz, CDCl3) δ 7.28 (t, J = 57.3 Hz, 2H), 7.25 - 7.10 (m, 1H), 7.04 - 6.99 (m, 2H), 4.66 (s, 2H), 3.96 (s, 3H), 3.63 - 3.57 (m, 1H), 2.38 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).151 1< H NMR (500 MHz, CDCl3) δ 7.20 (t, J = 57.3 Hz, 1H), 7.12 - 7.04 (m, 3H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 2.32 (s, 3H), 2.30 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).152 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 7.11 - 6.95 (m, 3H), 4.75 (s, 2H), 3.96 (s, 3H), 3.63 - 3.57 (m, 1H), 2.28 (s, 6H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).153 1< H NMR (500 MHz, CDC13) δ 7.38 (dd, J = 8.7, 4.9 Hz, 1H), 7.35 -7.25 (m, 1H), 7.22 (t, J = 57.3 Hz, 1H), 7.17 - 7.10 (m, 1H), 4.65 (s, 2H), 3.96 (s, 3H), 3.62 - 3.55 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).154 1< H NMR (500 MHz, CDCl3) δ 7.36 (t, J = 57.3 Hz, 1H), 7.34 - 7.11 (m, 2H), 7.02 (ddd, J = 8.8, 8.0, 1.9 Hz, 1H), 4.61 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).155 1< H NMR (500 MHz, CDCl3) δ 7.42 (dd, J = 5.0, 2.5 Hz, 1H), 7.38 -7.35 (m, 1H), 7.24 (t, J = 57.3 Hz, 1H), 7.15 - 7.09 (m, 1H), 4.69 (s, 2H), 3.96 (s, 3H), 3.62 - 3.55 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).156 1< H NMR (500 MHz, CDCl3) δ 7.62 (d, J = 2.0 Hz, 1H), 7.54 - 7.47 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).157 1< H NMR (500 MHz, CDCl3) δ 7.53 (dd, J = 10.6, 1.1 Hz, 1H), 7.37 (dd, J = 7.6, 1.2 Hz, 1H), 7.25 (t, J = 57.3 Hz, 1H), 7.15 - 7.10 (m, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).158 1< H NMR (500 MHz, CDC13) δ 7.72 (d, J = 2.0 Hz, 1H), 7.62 - 7.50 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 4.62 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).159 1< H NMR (500 MHz, CDC13) δ 7.77 (d, J = 1.9 Hz, 1H), 7.70 (dd, J = 9.3, 1.9 Hz, 1H), 7.56 (d, J = 9.2 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 4.61 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 3.21 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).160 1< H NMR (500 MHz, CDCl3) δ 8.04 (t, J = 1.9 Hz, 1H), 7.76 (ddd, J = 8.4, 1.8, 1.1 Hz, 1H), 7.63 (ddd, J = 7.9, 1.9, 1.2 Hz, 1H), 7.47 (dd, J = 8.5, 7.9 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 3.18 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).161 1< H NMR (500 MHz, CDCl3) δ 7.89 (dd, J = 8.4, 1.6 Hz, 1H), 7.68 (dd, J = 8.0, 1.7 Hz, 1H), 7.50 -7.38 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 4.53 (s, 2H), 3.96 (s, 3H), 3.63 - 3.55 (m, 1H), 3.20 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).162 1< H NMR (500 MHz, CDC13) δ 8.08 (d, J = 2.2 Hz, 1H), 7.66 (dd, J = 9.3, 2.2 Hz, 1H), 7.58 (d, J = 9.4 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.57 (m, 1H), 3.18 (s, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).163 1< H NMR (500 MHz, CDCl3) δ 7.82 - 7.70 (m, 4H), 7.23 (t, J= 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.66 - 3.56 (m, 1H), 3.27 (q, J = 9.2 Hz, 2H), 1.27 (t, J = 9.2 Hz, 3H), 0.75 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).164 1< H NMR (500 MHz, CDCl3) δ 8.13 (t, J = 1.9 Hz, 1H), 7.78 (ddd, J = 8.6, 2.0, 1.3 Hz, 1H), 7.63 (ddd, J = 7.9, 1.9, 1.2 Hz, 1H), 7.50 (dd, J = 8.5, 7.9 Hz, 1H), 7.23 (t, J = 57.3 Hz, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 3.28 (q, J = 9.1 Hz, 2H), 1.26 (t, J = 9.1 Hz, 3H), 0.74 - 0.65 (m, 2H), 0.65 - 0.56 (m, 2H).165 1< H NMR (500 MHz, CDCl3) δ 7.54 (d, J = 1.9 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.36 -7.28 (m, 1H), 7.21 (t, J = 57.3 Hz, 1H), 4.62 (s, 2H), 3.96 (s, 3H), 3.64 - 3.56 (m, 1H), 2.99 - 2.90 (m, 1H), 1.29 - 1.20 (m, 2H), 1.20 - 1.13 (m, 2H), 0.75 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).166 1< H NMR (500 MHz, CDCl3) δ 7.50 (dd, J = 9.0, 5.0 Hz, 1H), 7.36 -7.24 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.22 - 7.10 (m, 1H), 4.66 (s, 2H), 3.96 (s, 3H), 3.58 (s, 1H), 3.01 - 2.90 (m, 1H), 1.29 - 1.20 (m, 2H), 1.20 - 1.13 (m, 2H), 0.74 - 0.65 (m, 2H), 0.65 - 0.55 (m, 2H).168 1< H NMR (500 MHz, CDCl3) δ 7.44 (dd, J = 8.1, 1.8 Hz, 1H), 7.40 (dd, J = 8.0, 1.6 Hz, 1H), 7.37 (td, J = 7.7, 1.7 Hz, 1H), 7.33 - 7.26 (m, 1H), 7.20 (t, J = 57.3 Hz, 1H), 4.34 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).169 1< H NMR (500 MHz, CDCl3) δ 7.42 (t, J = 1.9 Hz, 1H), 7.38 (dt, J = 8.1, 1.6 Hz, 1H), 7.35 (t,J = 8.0 Hz, 1H), 7.24 (t, J = 57.3 Hz, 1H), 7.21 - 7.08 (m, 1H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J= 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).170 1< H NMR (500 MHz, CDCl3) δ 7.43 (d, J = 2.1 Hz, 1H), 7.34 - 7.26 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.13 (d, J = 35.8 Hz, 1H), 4.34 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.69 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).171 1< H NMR (500 MHz, CDCl3) δ 7.45 -7.39 (m, 2H), 7.36 (dd, J = 7.3, 2.4 Hz, 1H), 7.21 (t,J = 57.3 Hz, 1H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.69 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).172 1< H NMR (500 MHz, CDC13) δ 7.39 (dd, J = 9.3, 6.8 Hz, 1H), 7.36 -7.32 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 4.39 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.36 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).173 1< H NMR (500 MHz, CDCl3) δ 7.49 - 7.44 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 7.15 - 7.06 (m, 1H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).174 1< H NMR (500 MHz, CDCl3) δ 7.35 -7.30 (m, 3H), 7.20 (t, J = 57.3 Hz, 1H), 4.33 (q, J = 7.8 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J= 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).175 1< H NMR (500 MHz, CDC13) δ 7.31 (d, J = 16.1 Hz, 2H), 7.15 (t, J = 57.3 Hz, 1H), 4.39 (q,J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.36 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).176 1< H NMR (500 MHz, CDC13) δ 7.41 (dddd, i J= 8.8, 7.9, 5.0, 1.6 Hz, 1H), 7.39 -7.34 (m, 1H), 7.22 (t, J = 57.3 Hz, 1H), 7.18 - 7.09 (m, 2H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).177 1< H NMR (500 MHz, CDCl3) δ 7.36 - 7.32 (m, 1H), 7.24 (t, J = 57.3 Hz, 1H), 7.21 - 7.08 (m, 3H), 4.31 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).178 1< H NMR (500 MHz, CDCl3) δ 7.35 -7.30 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 7.07 - 7.00 (m, 2H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).179 1< H NMR (500 MHz, CDCl3) δ 7.24 (t, J = 57.3 Hz, 1H), 7.21 - 7.09 (m, 1H), 6.91 (td, J = 8.2, 2.0 Hz, 1H), 6.84 (td, J = 7.9, 1.9 Hz, 1H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).180 1< H NMR (500 MHz, CDC13) δ 7.34 - 7.29 (m, 1H), 7.21 (t, J = 57.3 Hz, 1H), 7.19 - 7.08 (m, 2H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).181 1< H NMR (500 MHz, CDCl3) δ 7.43 (tt, J = 7.8, 4.9 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 7.00 (td, J = 7.5, 0.9 Hz, 2H), 4.40 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.69 (m, 1H), 1.37 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).182 1< H NMR (500 MHz, CDC13) δ 7.21 (t, J = 57.3 Hz, 1H), 6.72 (tt, J = 8.1, 0.8 Hz, 2H), 4.40 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.37 (d, J = 7.5 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).183 1< H NMR (500 MHz, CDC13) δ 7.34 - 7.28 (m, 1H), 7.20 (t, J = 57.3 Hz, 1H), 7.14 - 7.02 (m, 2H), 4.32 (q, J = 7.8 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.68 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.79 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).184 1< H NMR (500 MHz, CDCl3) δ 7.49 -7.43 (m, 2H), 7.39 -7.34 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).185 1< H NMR (500 MHz, CDCl3) δ 7.64 - 7.57 (m, 1H), 7.48 - 7.43 (m, 1H), 7.34 - 7.29 (m, 2H), 7.23 (t, J = 57.3 Hz, 1H), 4.33 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).186 1< H NMR (500 MHz, CDC13) δ 7.58 - 7.55 (m, 1H), 7.55 - 7.51 (m, 1H), 7.34 - 7.28 (m, 2H), 7.24 (t, J = 57.3 Hz, 1H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J= 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).187 1< H NMR (500 MHz, CDC13) δ 7.72 (d, J = 1.9 Hz, 1H), 7.47 (dd, J = 8.7, 1.9 Hz, 1H), 7.34 - 7.25 (m, 1H), 7.15 (t,J = 57.3 Hz, 1H), 4.33 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).188 1< H NMR (500 MHz, CDCl3) δ 7.64 (d, J = 2.6 Hz, 1H), 7.60 (d, J = 7.8 Hz, 1H), 7.51 (dd, J = 7.8, 2.5 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 4.34 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.69 (m, 1H), 1.34 (d, J = 7.5 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).189 1< H NMR (500 MHz, CDC13) δ 7.52 (d, J = 8.1 Hz, 2H), 7.21 (t, J = 57.3 Hz, 1H), 7.10 - 7.04 (m, 1H), 4.36 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.70 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).190 1< H NMR (500 MHz, CDC13) δ 7.68 (s, 2H), 7.21 (t, J = 57.3 Hz, 1H), 4.36 (q, J= 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).191 1< H NMR (500 MHz, CDCl3) δ 7.64 (d, J = 1.9 Hz, 1H), 7.57 (d, J = 8.5 Hz, 1H), 7.34 - 7.24 (m, 1H), 7.18 (t, J = 57.3 Hz, 1H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.69 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).192 1< H NMR (500 MHz, CDC13) δ 7.34 - 7.21 (m, 1H), 7.19 (t, J = 57.3 Hz, 1H), 7.18 - 7.07 (m, 3H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.68 (m, 1H), 2.38 (s, 3H), 1.34 (d, J= 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).193 1< H NMR (500 MHz, CDC13) δ 7.21 (t, J = 57.3 Hz, 1H), 7.04 (d, J = 8.3 Hz, 1H), 6.95 - 6.91 (m, 1H), 6.90 (d, J = 1.8 Hz, 1H), 4.33 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 2.31 (s, 3H), 2.28 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).194 1< H NMR (500 MHz, CDC13) δ 7.21 (t, J = 57.3 Hz, 1H), 7.10 - 7.03 (m, 2H), 7.00 (d, J = 2.0 Hz, 1H), 4.34 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 2.38 (s, 3H), 2.37 (s, 3H), 1.34 (d, J= 7.6 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).195 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 7.13 - 7.09 (m, 1H), 7.00 (d, J = 7.7 Hz, 2H), 4.35 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 2.31 (s, 6H), 1.36 (d, J= 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).196 1< H NMR (500 MHz, CDC13) δ 7.21 (t, J = 57.3 Hz, 1H), 6.81 (s, 2H), 4.35 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.79 - 3.69 (m, 1H), 2.27 (s, 3H), 2.24 (s, 6H), 1.36 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).197 1< H NMR (500 MHz, CDCl3) δ 7.24 (t, J = 57.3 Hz, 1H), 7.18 - 7.12 (m, 1H), 7.12 - 7.08 (m, 2H), 4.34 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 3.09 - 3.00 (m, 1H), 2.38 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 1.30 (d, J = 6.6 Hz, 3H), 1.25 (d, J = 6.6 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).198 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.22 (m, 1H), 7.18 (t, J = 57.3 Hz, 1H), 7.07 (d, J = 1.9 Hz, 1H), 7.00 - 6.95 (m, 1H), 4.33 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.69 (m, 1H), 3.29 - 3.17 (m, 1H), 2.37 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 1.28 (d, J = 6.9 Hz, 3H), 1.23 (d, J = 6.9 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.65 (m, 2H).199 1< H NMR (500 MHz, CDCl3) δ 7.19 (t, J = 57.3 Hz, 1H), 7.10 (d, J = 2.7 Hz, 1H), 7.00 - 6.94 (m, 2H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.70 (m, 1H), 2.37 (d, J = 0.8 Hz, 3H), 1.35 (s, 3H), 1.34 (d, J = 6.9 Hz, 6H), 1.34 (d, J = 6.9 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).200 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.23 (m, 1H), 7.22 (t, J = 57.3 Hz, 1H), 7.17 - 7.08 (m, 1H), 7.04 (dq, J = 7.4, 1.0 Hz, 1H), 4.34 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 2.38 (d, J = 0.9 Hz, 3H), 1.34 (d, J = 7.7 Hz, 3H), 1.33 (s, 9H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).201 1< H NMR (500 MHz, CDCl3) δ 7.18 (t, J = 57.3 Hz, 1H), 7.12 - 7.09 (m, 1H), 7.09 - 7.05 (m, 2H), 4.33 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.69 (m, 1H), 2.96 - 2.85 (m, 1H), 2.38 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 1.30 (d, J = 6.6 Hz, 3H), 1.25 (d, J = 6.6 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).202 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.26 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.21 - 7.09 (m, 3H), 4.33 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.70 (m, 1H), 2.35 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).203 1< H NMR (500 MHz, CDCl3) δ 7.23 (t, J = 57.3 Hz, 1H), 7.16 - 7.10 (m, 2H), 7.08 (dt, J = 8.2, 0.6 Hz, 2H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.69 (m, 1H), 2.38 (s, 3H), 1.34 (d,J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).204 1< H NMR (500 MHz, CDC13) δ 7.21 (t, J = 57.3 Hz, 1H), 7.08 - 6.99 (m, 3H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 2.32 (d, J = 0.9 Hz, 3H), 2.30 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).205 1< H NMR (500 MHz, CDC13) δ 7.21 (t, J = 57.3 Hz, 1H), 6.97 (t, J = 2.3 Hz, 1H), 6.95 (d, J = 2.1 Hz, 2H), 4.33 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.69 (m, 1H), 2.28 (s, 6H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).206 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.30 (m, 1H), 7.30 - 7.25 (m, 1H), 7.23 (t, J = 57.3 Hz, 1H), 7.20 - 7.08 (m, 1H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).207 1< H NMR (500 MHz, CDCl3) δ 7.34 - 7.23 (m, 2H), 7.18 (t, J = 57.3 Hz, 1H), 7.05 (ddd, J = 8.6, 7.9, 1.8 Hz, 1H), 4.34 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J= 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).208 1< H NMR (500 MHz, CDCl3) δ 7.46 (dd, J = 5.0, 2.4 Hz, 1H), 7.36 (ddd, J = 7.5, 5.1, 2.6 Hz, 1H), 7.25 (t, J= 57.3 Hz, 1H), 7.19 - 7.08 (m, 1H), 4.35 (q, J= 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).209 1< H NMR (500 MHz, CDC13) δ 7.61 (d, J = 2.2 Hz, 1H), 7.57 (d, J = 57.3 Hz, 1H), 7.52 (dd, J = 7.3, 2.2 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.69 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).210 1< H NMR (500 MHz, CDCl3) δ 7.53 (dd, J = 10.6, 1.3 Hz, 1H), 7.35 -7.25 (m, 1H), 7.21 (t,J = 57.3 Hz, 1H), 7.18 - 7.06 (m, 1H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).211 1< H NMR (500 MHz, CDC13) δ 7.72 (d, J = 1.9 Hz, 1H), 7.56 (dd, J = 11.4, 1.9 Hz, 1H), 7.37 (d, J = 11.5 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 4.34 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).212 1< H NMR (500 MHz, CDC13) δ 7.74 (d, J = 1.9 Hz, 1H), 7.68 (dd, J = 9.5, 2.0 Hz, 1H), 7.49 (d, J = 9.5 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 4.34 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 3.21 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).213 1< H NMR (500 MHz, CDC13) δ 8.03 - 7.99 (m, 1H), 7.79 - 7.73 (m, 1H), 7.50 - 7.42 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 4.31 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.70 (m, 1H), 3.18 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).214 1< H NMR (500 MHz, CDCl3) δ 7.88 (dd, J = 8.0, 2.0 Hz, 1H), 7.58 (dd, J = 7.8, 2.1 Hz, 1H), 7.50 - 7.41 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 4.31 (q, J = 7.6 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 3.20 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).215 1< H NMR (500 MHz, CDCl3) δ 7.92 (d, J = 2.2 Hz, 1H), 7.66 (dd, J = 9.3, 2.2 Hz, 1H), 7.57 (d, J = 9.4 Hz, 1H), 7.21 (t, J = 57.3 Hz, 1H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.69 (m, 1H), 3.18 (s, 3H), 1.34 (d, J = 7.7 Hz, 3H), 0.78 - 0.72 (m, 2H), 0.72 - 0.67 (m, 2H).216 1< H NMR (500 MHz, CDC13) δ 7.83 - 7.76 (m, 2H), 7.57 - 7.50 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 4.32 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.69 (m, 1H), 3.27 (q, J= 9.2, 1.4 Hz, 2H), 1.34 (d, J = 7.7 Hz, 3H), 1.27 (t, J = 9.2 Hz, 3H), 0.79 - 0.72 (m, 2H), 0.72 - 0.64 (m, 2H).217 1< H NMR (500 MHz, CDC13) δ 7.83 - 7.74 (m, 2H), 7.52 - 7.44 (m, 2H), 7.21 (t, J = 57.3 Hz, 1H), 4.31 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.77 - 3.70 (m, 1H), 3.28 (q, J = 9.2, 2.6 Hz, 2H), 1.34 (d, J = 7.7 Hz, 3H), 1.26 (t, J = 9.1 Hz, 3H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).218 1< H NMR (500 MHz, CDCl3) δ 7.49 (d, J = 1.9 Hz, 1H), 7.35 - 7.29 (m, 1H), 7.28 (d, J = 11.1 Hz, 1H), 7.19 (t, J = 57.3 Hz, 1H), 4.34 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.69 (m, 1H), 2.98 - 2.90 (m, 1H), 1.34 (d, J = 7.7 Hz, 3H), 1.29 - 1.20 (m, 2H), 1.20 - 1.10 (m, 2H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H).2191H NMR (500 MHz, CDCl3) δ 7.36 - 7.32 (m, 1H), 7.32 - 7.23 (m, 1H), 7.22 (t, J = 57.3 Hz, 1H), 7.21 - 7.08 (m, 1H), 4.35 (q, J = 7.7 Hz, 1H), 3.96 (s, 3H), 3.78 - 3.69 (m, 1H), 2.99 - 2.90 (m, 1H), 1.35 (d, J = 7.7 Hz, 3H), 1.28 - 1.20 (m, 2H), 1.20 - 1.13 (m, 2H), 0.77 - 0.72 (m, 2H), 0.72 - 0.66 (m, 2H). Test example 1Enzyme Activity assay

[0044] The inhibitory activities of control agents and target compounds on succinate dehydrogenase are determined.

[0045] The enzyme used in this test example is succinate dehydrogenase, which is isolated from porcine hearts.

[0046] The test method comprises the following steps: The total volume of the system is 1.8 ml, and the system contained 100 mM Na 2 HPO 4 -NaH 2 PO 4 buffer (pH=7.4), 0.3 mM EDTA, 20 mM sodium succinate, 53µM DCIP (2,6-dichloroindophenol sodium), and 2nM succinate dehydrogenase. Thermostatic waterbath at 23 °C and magnetic stirring at 600 rpm. The decrease in the light absorption of the substrate DCIP is monitored at a wavelength of 600 nm and experimental points in a linear range are collected. Control substrate consumption not more than 5% of the experimental points. The molar extinction coefficient of DCIP is 21 mM -1< cm -1< . And calculating the reduction yield of the DCIP in the reaction time, fitting a linear slope, and deducting the baseline slope to obtain the initial reaction speed.

[0047] The test results are shown in Table 2. TABLE 2Compound numberInhibitors (10 µM, SQR)Compound numberInhibitors (10 µM, SQR)Compound numberInhibitors (10 µM, SQR)1>90%74>90%147>90%2>90%75>90%148>90%3>90%76>90%149>90%4>90%77>90%150>90%5>90%78>90%151>90%6>90%79>90%152>90%7>90%80>90%153>90%8>90%81>90%154>90%9>90%82>90%155>90%10>90%83>90%156>90%11>90%84>90%157>90%12>90%85>90%158>90%13>90%86>90%159>90%14>90%87>90%160>90%15>90%88>90%161>90%16>90%89>90%162>90%17>90%90>90%163>90%18>90%91>90%164>90%19>90%92>90%165>90%20>90%93>90%166>90%21>90%94>90%22>90%95>90%168>90%23>90%96>90%169>90%24>90%97>90%170>90%25>90%98>90%171>90%26>90%99>90%172>90%27>90%100>90%173>90%28>90%101>90%174>90%29>90%102>90%175>90%30>90%103>90%176>90%31>90%104>90%177>90%32>90%105>90%178>90%33>90%106>90%179>90%34>90%107>90%180>90%35>90%108>90%181>90%36>90%109>90%182>90%37>90%110>90%183>90%38>90%111>90%184>90%39>90%112>90%185>90%40>90%186>90%41>90%187>90%42>90%115>90%188>90%43>90%116>90%189>90%44>90%117>90%190>90%45>90%118>90%191>90%46>90%119>90%192>90%47>90%120>90%193>90%48>90%121>90%194>90%49>90%122>90%195>90%50>90%123>90%196>90%51>90%124>90%197>90%52>90%125>90%198>90%53>90%126>90%199>90%54>90%127>90%200>90%55>90%128>90%201>90%56>90%129>90%202>90%57>90%130>90%203>90%58>90%131>90%204>90%59>90%132>90%205>90%60>90%133>90%206>90%61>90%134>90%207>90%62>90%135>90%208>90%63>90%136>90%209>90%64>90%137>90%210>90%65>90%138>90%211>90%66>90%139>90%212>90%67>90%140>90%213>90%68>90%141>90%214>90%69>90%142>90%215>90%70>90%143>90%216>90%71>90%144>90%217>90%72>90%145>90%218>90%73>90%146>90%219>90%

[0048] The enzyme activity test result shows that the compound provided by the invention has excellent inhibitory activity on succinate dehydrogenase.Test example 2Fungicidal activity test

[0049] The fungicidal activity of the control agents and target compounds are determined.Erysiphe graminis

[0050] The test and investigation method refers to SOP-SC-1116 erysiphe graminis potting method in disinfectant rolls written by KANGZHUO and GUBAOGEN in "Standard operation specification for testing biological activity of pesticides".Sphaerotheca fuliginea

[0051] The test and investigation method refers to SOP-SC-1101 sphaerotheca fuliginea potting method in disinfectant rolls written by KANGZHUO and GUBAOGEN in "Standard operation specification for testing biological activity of pesticides".

[0052] The controlling effect are shown in table 3 and table 4. TABLE 3Erysiphe graminis100 mg / L25 mg / L6.25 mg / LCompounds 1 to 33AAACompound 34AABCompound 35AABCompound 36AAACompound 37AABCompound 38AABCompounds 39-112, 115-166 and 168-219AAAPydiflumetofenAAAFenaminstrobinAABProthioconazoleAAB

[0053] In table 3, A and B both represent control ratings, and 80% ≦ A ≦ 100%; 70% ≦ B<80%; C<70%. TABLE 4Compound numberSphaerotheca fuligineaCompound numberSphaerotheca fuligineaCompound numberSphaerotheca fuliginea100 mg / L100 mg / L100 mg / L1A75A149A2A76A150A3A77A151A4C78A152A5C79A153A6A80A154A7A81A155A8A82A156A9C83A157A10A84A158A11A85A159A12B86A160A13A87A161A14A88A162A15B89A163A16B90A164A17A91A165A18A92A166A19A93A20A94A168A21B95A169A22A96A170A23A97A171A24A98A172A25A99A173A26A100A174A27A101A175A28A102A176A29A103A177A30A104A178A31A105A179A32B106A180A33A107A181A34A108A182A35A109A183A36A110A184A37B111A185A38B112A186A39B187A40B188A41A115A189A42A116A190A43A117A191A44A118A192A45A119A193A46A120A194A47A121A195A48A122A196A49A123A197A50A124A198A51A125A199A52A126A200A53B127A201A54A128A202A55A129A203A56A130A204A57A131A205A58A132A206A59A133A207A60A134A208A61A135A209A62A136A210A63A137A211A64A138A212A65A139A213A66A140A214A67A141A215A68A142A216A69A143A217A70A144A218A71A145A219A72A146APydiflumetofenA73A147AProthioconazoleB74A148AFenaminstrobinB

[0054] In table 4, A and B both represent control ratings, and 80% ≦ A ≦ 100%; 70% ≦ B<80%; C<70%.Test example 3Compound 1 is tested for isolated hyphae.

[0055] First, the pathogenic fungi to be tested are primarily screened. The mycelial growth rate method is used to determine the inhibitory effect of the medicament on the mycelial growth of several tested pathogens. Take a plate with a diameter of 5 mm from the edge of the colony that has been continuously transferred and cultured for 4 days, and the plate is inoculated on PDA plates containing the medicament concentrations of 25µg / mL, 6.25µg / mL, 1.5625µg / mL, respectively, and 3 replicates of each treatment are performed. All dishes are incubated in a sterile 25 °C incubator. When the blank control fungi grow to 2 / 3 of the diameter of the culture dish, the diameters of the control and treated colonies are measured by adopting a cross method, and the hypha growth inhibition rate is calculated.

[0056] The results are shown in table 5. TABLE 5Compou ndConcen trationInhibition ratio (%)Number ofµg / mLPhy top hth ora infe stan sScle rotin ia scler otior umGibbe rella zeaeRhizo ctonia cereal isAlter naria altern ataAlter naria solaniPhyto phtho ra capsic iFusari um wilt of water melonCorn big spotPydiflu metofen1.5625ACAAAABAA6.25AAAAAAAAA25AAAAAAAAACompou nd 11.5625ACACAABAA6.25AAABAAAAA25AAAAAAAAA

[0057] The results of fungicidal activity test in vivo and in vitro mycelium show that the compound provided by the invention has excellent fungicidal activity on plant fungal diseasess, such as at least one of erysiphe graminis, sphaerotheca fuliginea, wheat scab, rice bakanae disease, sclerotinia rot of colza, corn small leaf spot, wheat stripe rust and cucumber gray mold, and most of the compounds are superior to commercialized control pydiflumetofen, fenaminstrobin and prothioconazole, and part of the compounds are basically equivalent to the current commercialized medicaments with the best powdery mildew.Test example 4Compound 1 for field test of sphaerotheca fuliginea

[0058] The test is carried out according to GB / T17980.30-2000 of pesticide field efficacy test guidelines. The survey method is to randomly take four points for each cell and survey all leaves of 2 plants per point. And investigating the sphaerotheca fuliginea incidence before the first application, and investigating the sphaerotheca fuliginea incidence 7 and 14 days after the second application respectively, and calculating the disease index and the controlling effect. The results are shown in table 6. TABLE 6GroupMedicamentControlling effect %1Compound 1 at 50 mg / L822Compound 1 at 100 mg / L883Compound 1 at 200 mg / L924Pydiflumetofen 100 mg / L92529% Isopyrazam-azoxystrobin suspension (Reflect Xtra) 100 mg / L956CK72 (disease index)

[0059] From the field test results of sphaerotheca fuliginea, the compound 1 can still maintain the controlling effect of more than 80% at the concentration of 50 mg / L. At 100 mg / L concentration, compound 1 has the same control effect as the current mainstream insecticides against sphaerotheca fuliginea, and it has strong development value.Test example 5

[0060] Test of protective activity and therapeutic activity of Compound 1 against rice bakanae disease.

[0061] The test and investigation method refers to SOP-SC-1112 rice bakanae disease potting method in disinfectant rolls written by KANGZHUO and GUBAOGEN in "Standard operation specification for testing biological activity of pesticides".

[0062] The phenamacril is a mainstream medicament for preventing and treating the rice bakanae disease at present, resistant strains are more and more along with long-time use, and two strains showing sensitivity and one strain showing resistance to the cyhalothrin are selected as test strains.

[0063] Four Fusarium fujikura SX18-32, SX18-50, SX18-59 and SX18-63 are selected for testing strains, and the current mainstream commercial bactericide phenamacril is selected as a positive control. Wherein SX18-32, SX18-50 and SX18-59 show sensitivity to phenamacril and SX18-63 show resistance to phenamacril. Their protective and therapeutic activities are listed in table 7 and table 8.

[0064] From the test of the therapeutic activity, it is obvious that the compound 1 of the invention has far better therapeutic effect particularly on a resistant strain SX18-63(R) than the phenamacril, the phenamacril has almost no therapeutic activity on the resistant strain, in addition, the phenamacril has only about 50 percent of therapeutic effect at most on a sensitive strain, and the compound 1 of the invention has 96.8 percent of strong therapeutic effect on SX18-59 (S).

[0065] In the test of the protective activity, the protective activity of the compound 1 of the invention on three strains is more than 90 percent, it is close to complete protection and it is also far superior to the phenamacril.

[0066] In conclusion, the compound 1 has better therapeutic activity and protective activity on the rice bakanae disease than the current mainstream medicament of phenamacril, and it has great development prospect.

[0067] The preferred embodiments of the invention have been described above in detail, but the invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including various technical features being combined in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.

Claims

1. A dendrene amide compound, wherein the compound has the structure shown in formula (I), wherein, in the formula (I), X is F; R1 and R2 are each independently selected from H, methyl, ethyl, n-propyl; R31, R32, R33, R34 and R35 are each independently selected from H, F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, trifluoromethyl, C1-3 alkylsulfonyl, ethoxy, substituted or unsubstituted ethynyl; the optional substituents on R31, R32, R33, R34 and R35 are selected from at least one of methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl; R4 is cyclopropyl; R51 is difluoromethyl; R52 is methyl; R61 and R62 are each independently selected from H, F, Cl, Br.

2. The compound according to claim 1, wherein the compound of formula (I) is selected from at least one of the following compounds: Compoun d numberStructureCompoun d numberStructure1 110 2 111 3 112 4 5 6 115 7 116 8 117 9 118 10 119 11 120 12 121 13 122 14 123 15 124 16 125 17 126 18 127 19 128 20 129 21 130 22 131 23 132 24 133 25 134 26 135 27 136 28 137 29 138 30 139 31 140 32 141 33 142 34 143 35 144 36 145 37 146 38 147 39 148 40 149 41 150 42 151 43 152 44 153 45 154 46 155 47 156 48 157 49 158 50 159 51 160 52 161 53 162 54 163 55 164 56 165 57 166 58 59 168 60 169 61 170 62 171 63 172 64 173 65 174 66 175 67 176 68 177 69 178 70 179 71 180 72 181 73 182 74 183 75 184 76 185 77 186 78 187 79 188 80 189 81 190 82 191 83 192 84 193 85 194 86 195 87 196 88 197 89 198 90 199 91 200 92 201 93 202 94 203 95 204 96 205 97 206 98 207 99 208 100 209 101 210 102 211 103 212 104 213 105 214 106 215 107 216 108 217 109 218 219 3. Use of a compound according to claim 1 or 2 as succinate dehydrogenase inhibitor in pesticides.

4. Use of a compound according to claim 1 or 2 for controlling fungal plant diseases.

5. A bactericide, wherein the bactericide comprises an auxiliary material and an active ingredient selected from at least one of the compounds of claim 1 or 2; the active ingredient is contained in the bactericide in an amount of 5% to 99.99% by weight.

6. The bactericide according to claim 5, wherein the dosage form of the bactericide is at least one selected from emulsifiable concentrates, suspending agents, wettable powders, dusts, granules, aqueous solutions, poison baits, mother liquors and mother powders.

7. Use of the bactericide according to claim 5 or 6 for controlling fungal plant diseases.

8. Use according to claim 7, wherein the plant fungal diseases is selected from at least one of erysiphe graminis, sphaerotheca fuliginea, wheat scab, rice bakanae disease, sclerotinia rot of colza, corn leaf spot, wheat stripe rust and cucumber gray mold.