Abstract
An alkene-containing carboxylic ester compound of formula (I) and its agriculturally acceptable salt can be used as a herbicide.
##STR00001##
Claims
1. An alkene-containing carboxylic ester compound, characterized in that the compound is shown in formula I: ##STR01792## in the formula: X.sub.1 is selected from halogen, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 alkyl or C.sub.1-C.sub.6 haloalkyl; W is selected from CX.sub.2; X.sub.2 is selected from Y.sub.1 oxy, Y.sub.1 sulfonyl, Y.sub.1 oxy C.sub.1-C.sub.6 alkyl, Y.sub.1 sulfonyl C.sub.1-C.sub.6 alkyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms; the hydrogen on the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, phenyl or halophenyl; Y.sub.1 is selected from C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms or 5-7 membered aromatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, phenyl or halophenyl; X.sub.3 is selected from halogen, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 alkyl or C.sub.1-C.sub.6 haloalkyl; when X.sub.1 is selected from chlorine and X.sub.3 is selected from methylsulfonyl, X.sub.2 is not 2-thiazolyl; Z.sub.1 is selected from C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkylsulfonyl C.sub.1-C.sub.6 alkyl or phenyl; Z.sub.2 is selected from H, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 haloalkyl or phenyl; hydrogen on the phenyl mentioned above can be substituted by one or more of the following substituents; and the substituents are selected from halogen, cyano, nitro, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl or C.sub.1-C.sub.6haloalkyl; Q is selected from Q.sub.1 or Q.sub.2 group; ##STR01793## Q.sub.2 is selected from C.sub.3-C.sub.8 cycloalkenyl; the hydrogen on the ring can be substituted by the following substituents; the following substituents are selected from nitro, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.1-C.sub.6 alkenyl or C.sub.3-C.sub.6 cycloalkyl; when Q is selected from Q.sub.2, Z.sub.2 is not cyclopropyl; R.sub.1 to R.sub.5 are independently selected from hydrogen, cyano, nitro, halogen, phenyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.2-C.sub.6 haloalkynyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.1-C.sub.6 alkylthio or benzyloxy; wherein R.sub.1 and R.sub.2 form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; R.sub.2 and R.sub.3 can form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; a stereoisomer of the compound of the above formula I; or, the compound of the formula I and agriculturally acceptable salt of the isomer.
2. The compound according to claim 1, characterized in that in the formula I: X.sub.1 is selected from halogen, or C.sub.1-C.sub.6 alkyl; W is selected from CX.sub.2; X.sub.2 is selected from Y.sub.1 oxy; Y.sub.1 is selected from C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms; the hydrogen on the phenyl, the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.3-C.sub.6 cycloalkyl or C.sub.3-C.sub.6 cycloalkoxy; X.sub.3 is selected from C.sub.1-C.sub.6 alkylsulfonyl; Z.sub.1 is selected from C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl or phenyl; Z.sub.2 is selected from H, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl or phenyl; hydrogen on the phenyl mentioned above can be substituted by one or more of the following substituents; and the substituents are selected from halogen, cyano, nitro, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl or C.sub.1-C.sub.6 haloalkyl; Q is selected from Q.sub.1 or Q.sub.2 group; ##STR01794## Q.sub.2 is selected from C.sub.3-C.sub.8 cycloalkenyl; the hydrogen on the ring can be substituted by the following substituents; the following substituents are selected from nitro, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.1-C.sub.6 alkenyl or C.sub.3-C.sub.6 cycloalkyl; R.sub.1 to R.sub.5 are independently selected from hydrogen, cyano, nitro, halogen, phenyl, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 alkylthio or benzyloxy; wherein R.sub.1 and R.sub.2 form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; R.sub.2 and R.sub.3 can form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-3 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-3 heteroatoms together with the carbon atoms on the connected benzene ring; the Q of the above formula I is selected from a stereoisomer of the compound shown by Q.sub.1.
3. The compound according to claim 2, characterized in that in the formula I: X.sub.1 is selected from halogen or C.sub.1-C.sub.3 alkyl; W is selected from CX.sub.2; X.sub.2 is selected from Y.sub.1 oxy; Y.sub.1 is selected from C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms; the hydrogen on the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.3-C.sub.6 cycloalkyl or C.sub.3-C.sub.6 cycloalkoxy; X.sub.3 is selected from C.sub.1-C.sub.3 alkylsulfonyl; Z.sub.1 is selected from C.sub.1-C.sub.6 alkyl or C.sub.3-C.sub.6 cycloalkyl; Z.sub.2 is selected from or C.sub.1-C.sub.6 alkyl; Q is selected from Q.sub.1 or Q.sub.2 group; ##STR01795## Q.sub.2 is selected from cycloalkenyl; the hydrogen on the ring may be substituted by the following substituents which are selected from C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy or C.sub.1-C.sub.6 alkenyl; R.sub.1 to R.sub.5 are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or benzyloxy; the Q of the above formula I is selected from a stereoisomer of the compound shown by Q.sub.1.
4. The compound according to claim 3, characterized in that in the formula I: X.sub.1 is selected from halogen or C.sub.1-C.sub.3 alkyl; W is selected from CX.sub.2; X.sub.2 is selected from Y.sub.1 oxy; Y.sub.1 is selected from C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms or a 5-7 membered aromatic heterocyclic C.sub.1-C.sub.6 alkyl containing 1-4 heteroatoms; the hydrogen on the aliphatic heterocycle and the aromatic heterocycle mentioned above may be substituted by one or more of the following substituents which are selected from nitro, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.3-C.sub.6 cycloalkyl or C.sub.3-C.sub.6 cycloalkoxy; X.sub.3 is selected from C.sub.1-C.sub.3 alkylsulfonyl; Z.sub.1 is selected from C.sub.1-C.sub.3 alkyl; Z.sub.2 is selected from H or C.sub.1-C.sub.3 alkyl; Q is selected from Q.sub.1 or Q.sub.2 group; ##STR01796## Q.sub.2 is selected from G1, G2, G3, G4, G5 or G6 group; ##STR01797## R.sub.1 to R.sub.5 are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, methyl, ethyl, propyl, vinyl, propenyl, ethynyl, propynyl, methoxy, ethoxyl, benzyloxy, trifluoromethyl or trifluoromethoxy; the Q of the above formula I is selected from a trans-stereoisomer of the compound shown by Q.sub.1.
5. An application of the compound of the formula I of claim 1, characterized in the application of the compound of the formula I and the stereoisomer thereof or the compound of the formula I and the agriculturally acceptable salt of the isomer in control for weeds.
6. A herbicidal composition, characterized in that the herbicidal composition comprises an active ingredient and an agriculturally acceptable carrier; the active ingredient is a stereoisomer of the compound of the formula I of claim 1, or the compound of the formula I and agriculturally acceptable salt of the isomer; the weight percentage of the active ingredient in the composition is 1-99%.
7. A method for controlling weeds by the composition of claim 6, characterized in that a herbicidally effective dose of the herbicidal composition of claim 6 is applied to a weed or a growth medium or site of the weed.
Description
DETAILED DESCRIPTION
[0087] The following examples and biometric test results can be used to further illustrate the present invention, but are not intended to limit the present invention.
Synthesis Example
Embodiment 1 Synthesis of Compound 1-1
(1) Synthesis of 2-methanesulfonyl-4-trifluoromethyl benzoyl chloride
[0088] ##STR00013##
[0089] 2-methanesulfonyl-4-trifluoromethylbenzoic acid (30 g, 112 mmol) and toluene (200 ml) were added to a reaction flask; thionyl chloride (53 g, 447 mmol) was slowly added; the mixture was heated and refluxed for 4 hours; and the solvent was evaporated under reduced pressure to obtain 32 g of yellow solid, which is directly used in the next step.
(2) Synthesis of 2-methanesulfonyl-4-trifluoromethyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester
[0090] ##STR00014##
[0091] 1,3-dimethyl-5-hydroxypyrazole (13 g, 112 mmol), 1,2-dichloroethane (200 ml) and triethylamine (34 g, 336 mmol) were added to the reaction flask, and the 1,2-dichloroethane solution (100 ml) of 2-methanesulfonyl-4-trifluoromethyl benzoyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (1000 ml) was added to the residue; water (500 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (500 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 28 g of yellow solid, with a yield of 68%.
(3) Synthesis of 1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole
[0092] ##STR00015##
[0093] 2-methanesulfonyl-4-trifluoromethyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester (6 g, 16.6 mmol), 1,2-dichloroethane (50 ml), triethylamine (15 g, 148 mmol) and acetone cyanohydrin (1 ml) were added to the reaction flask; the mixture was kept at 60° C. to react for 6 hours and cooled to room temperature; water (100 ml) was added to the reaction solution, and shaken thoroughly and layered; the pH of the aqueous phase was adjusted to be 2-3 with 20% hydrochloric acid, and the aqueous phase was extracted twice with ethyl acetate (100 ml). The organic phase was washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; and the solvent was evaporated under reduced pressure to obtain 5.4 g of red oil with a yield of 90%.
(4) Synthesis of Cinnamyl Chloride
[0094] ##STR00016##
[0095] Cinnamic acid (0.17 g, 1.1 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (0.7 g, 5.5 mmol) was slowly added; the mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 0.18 g of pale yellow solid which was used directly in the next step.
(5) Synthesis of Compound 1-1
[0096] ##STR00017##
[0097] 1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml) of cinnamyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.35 g of white solid compound 1, with a purity of 99.3% and a yield of 64%.
Embodiment 2 Synthesis of Compound 1-7
(1) Synthesis of 3,4-(methylenedioxy) cinnamyl Chloride
[0098] ##STR00018##
[0099] 3,4-(methylenedioxy) cinnamic acid (0.21 g, 1.1 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (0.7 g, 5.5 mmol) was slowly added; the mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 0.23 g of pale yellow solid which was used directly in the next step.
(2) Synthesis of Compound 1-7
[0100] ##STR00019##
[0101] 1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol, see step 3 of embodiment 1 for preparation), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml) of 3,4-(methylenedioxy) cinnamyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.38 g of pale yellow solid compound 7, with a purity of 94.6% and a yield of 60.7%.
Embodiment 3 Synthesis of Compound 2-379
(1) Synthesis of 1-cyclohexenoyl Chloride
[0102] ##STR00020##
[0103] 1-cyclohexenoic acid (0.14 g, 1.1 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (0.7 g, 5.5 mmol) was slowly added; the mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 0.16 g of pale yellow solid which was used directly in the next step.
(2) Synthesis of Compound 2-379
[0104] ##STR00021##
[0105] 1,3-dimethyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol, see step 3 of embodiment 1 for preparation), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml) of 1-cyclohexenoyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent is evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.4 g of off-white solid compound 2-379, with a purity of 99.4% and a yield of 77.1%.
Embodiment 4 Synthesis of Compound 1-16
(1) Synthesis of 2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl chloride
[0106] ##STR00022##
[0107] 2-methanesulfonyl-4-trifluoromethylbenzoic acid (4 g, 14.35 mmol), dichloromethane (30 ml) and DMF (1 drop) were added into the reaction flask; oxalyl chloride (9.11 g, 71.8 mmol) was slowly added; the mixture was stirred at room temperature for 40 minutes; the solvent was evaporated under reduced pressure; toluene (15 ml) was added to the residue and stirred for 3 minutes; and then the solvent was evaporated under reduced pressure to obtain 4.26 g of yellow solid which was used directly in the next step.
(2) Synthesis of 2-chloro-3-methoxymethyl-4-methylsulfonyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester
[0108] ##STR00023##
[0109] 1,3-dimethyl-5-hydroxypyrazole (1.77 g, 15.79 mmol), dichloroethane (100 ml) and triethylamine (2.9 g, 28.7 mmol) were added to the reaction flask, and the dichloroethane solution (30 ml) of 2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (1000 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (100 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 3.4 g of off-white solid, with a yield of 63.5%.
(3) Synthesis of 1,3-dimethyl-4-(2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl)-5-hydroxypyrazole
[0110] ##STR00024##
[0111] 2-chloro-3-methoxymethyl-4-methylsulfonyl benzoic acid (1,3-dimethylpyrazole-5-yl) ester (3.4 g, 9.12 mmol), dichloromethane (100 ml), triethylamine (1.38 g, 13.68 mmol) and acetone cyanohydrin (1 ml) were added to the reaction flask to react at room temperature for 12 hours; and water extraction (50 ml (3)) was added to the reaction solution. After the aqueous phase was collected, the pH was adjusted to be 2-3 with 20% hydrochloric acid, and the aqueous phase was extracted twice with ethyl acetate (100 ml). The organic phase was washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; and the solvent was evaporated under reduced pressure to obtain 3.26 g of yellow solid with a yield of 96%.
(4) Synthesis of Compound 1-16
[0112] ##STR00025##
[0113] 1,3-dimethyl-4-(2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl)-5-hydroxypyrazole (0.4 g, 1.07 mmol), dichloromethane (20 ml) and triethylamine (0.22 g, 2.15 mmol) were added to the reaction flask, and the dichloromethane solution (15 ml, see step 4 of embodiment 1 for preparation) of cinnamyl chloride in the above step was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.31 g of white solid compound 16, with a purity of 93.2% and a yield of 53.5%.
Embodiment 5 Synthesis of Compound 2-307
[0114] ##STR00026##
[0115] 1,3-dimethyl-4-(2-chloro-3-methoxymethyl-4-methylsulfonyl benzoyl)-5-hydroxypyrazole (0.4 g, 1.1 mmol, see step 3 of embodiment 4 for preparation), dichloromethane (20 ml) and triethylamine (0.22 g, 2.2 mmol) were added to the reaction flask, and the dichloromethane solution of 1-cyclohexene-1-acyl chloride (0.2 g of 1.1 mmol 1-cyclohexene-1-acyl chloride was dissolved in 15 ml of dichloromethane, see step 1 of embodiment 3 for preparation) was added dropwise. The mixture was stirred at room temperature for 1 hour; the solvent was evaporated under reduced pressure; ethyl acetate (100 ml) was added to the residue; water (50 ml) was used for separation and extraction; the organic phase was sequentially washed with saturated salt water (50 ml) and dried with anhydrous magnesium sulfate; the solvent was evaporated under reduced pressure; and the residue was separated by column chromatography to obtain 0.45 g of white solid, with a purity of 99.6% and a yield of 87%.
[0116] The initial substances are replaced according to the above recorded method to obtain other compounds shown by the formula I. Part of the compounds of the formula I can be found in Table 1, Table 2, Table 3 and Table 4, wherein in Table 1 and Table 2, W is selected from CX.sub.2 and the stereo configuration in Table 1 is trans; in Table 3 and Table 4, W is selected from N and the stereo configuration in Table 3 is trans.
[0117] In the compound of the formula I, W is CX.sub.2 and the stereo configuration is trans.
##STR00027##
TABLE-US-00001 TABLE 1 Structures and Physical Properties of Part of Compounds of Formula 1 Appearance Com- (Melting pound X.sub.1 X.sub.2 X.sub.3 Z.sub.1 Z.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 Point° C.) 1-1 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 H H H H H white solid (144-146) 1-2 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 Cl H Cl H H 1-3 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H 1-4 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 H H NO.sub.2 H H 1-5 SO.sub.2CH.sub.3 H CF.sub.5 CH.sub.3 CH.sub.3 H H CH.sub.3 H H 1-6 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 H H [00028]
H H 1-7 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 H [00029]
H H pale yellow solid (99-101) 1-8 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 H [00030]
H H 1-9 SO.sub.2CH.sub.3 H CF.sub.5 CH.sub.3 CH.sub.3 H [00031]
H H 1-10 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 [00032]
H H H 1-11 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CF.sub.3 H H H H H 1-12 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 H H H H H H 1-13 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H H H H H 1-14 SO.sub.2CH.sub.3 H CF.sub.3 [00033]
CH.sub.3 H H H H H 1-15 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 [00034]
H H H H H 1-16 Cl [00035]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H white solid (139-141) 1-17 Cl [00036]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 Cl H Cl H H 1-18 Cl [00037]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H white solid (151-153) 1-19 Cl [00038]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H NO.sub.2 H H 1-20 Cl [00039]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H CF.sub.3 H H white solid (139-141) 1-21 Cl [00040]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H [00041]
H H pale pink solid (195-197) 1-22 Cl [00042]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00043]
H H pale yellow solid (160-162) 1-23 Cl [00044]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00045]
H H 1-24 Cl [00046]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00047]
H H 1-25 Cl [00048]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00049]
H H H 1-26 Cl [00050]
SO2CH.sub.3 CH.sub.3 CF.sub.3 H H H H H 1-27 Cl [00051]
SO.sub.2CH.sub.3 CH.sub.3 H H H H H H 1-28 Cl [00052]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H H H H H 1-29 Cl [00053]
SO.sub.2CH.sub.3 [00054]
CH.sub.3 H H H H H U 1-30 Cl [00055]
SO.sub.2CH.sub.3 CH.sub.3 [00056]
H H H H H 1-31 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H pale yellow solid (199-201) 1-32 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 Cl H Cl H H 1-33 Cl CH.sub.3 CO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H 1-34 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H NO.sub.3 H H 1-35 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H CF.sub.3 H H 1-36 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H [00057]
H H 1-37 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00058]
H H white solid (227-229) 1-38 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00059]
H H 1-39 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00060]
H H 1-40 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00061]
H H H 1-41 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CF.sub.3 H H H H H 1-42 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H H [00062]
H H yellow solid (151-152) 1-43 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H H H H H 1-44 Cl CH.sub.3 SO.sub.2CH.sub.3 [00063]
CH.sub.3 H H H H H 1-45 Cl CH.sub.3 SO.CH, CH.sub.3 [00064]
H H H H H 1-46 Cl [00065]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-47 Cl [00066]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 Cl H Cl H H 1-48 Cl [00067]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H 1-49 Cl [00068]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H NO.sub.2 H H 1-50 Cl [00069]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H CF.sub.3 H H 1-51 Cl [00070]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H [00071]
H H 1-52 Cl [00072]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00073]
H H 1-53 Cl [00074]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00075]
H H 1-54 Cl [00076]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00077]
H H 1-55 Cl [00078]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00079]
H H H 1-56 Cl [00080]
SO.sub.2CH.sub.3 CH.sub.3 CF.sub.3 H H H H H 1-57 Cl [00081]
SO.sub.2CH.sub.3 CH.sub.3 H H H H H H 1-58 Cl [00082]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H H H H H 1-59 Cl [00083]
SO.sub.2CH.sub.3 [00084]
CH.sub.3 H H H H H 1-60 Cl [00085]
SO.sub.2CH.sub.3 CH.sub.3 [00086]
H H H H H 1-61 Cl [00087]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-62 Cl [00088]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 Cl H Cl H H 1-63 Cl [00089]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H 1-64 Cl [00090]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H NO.sub.2 H H 1-65 Cl [00091]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H CF.sub.3 H H 1-66 Cl [00092]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H [00093]
H H 1-67 Cl [00094]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00095]
H H 1-68 Cl [00096]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00097]
H H 1-69 Cl [00098]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00099]
H H 1-70 Cl [00100]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00101]
H H H 1-71 Cl [00102]
SO.sub.2CH.sub.3 CH.sub.3 CF.sub.3 H H H H H 1-72 Cl [00103]
SO.sub.2CH.sub.3 CH.sub.3 H H H H H H 1-73 Cl [00104]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H H H H H 1-74 Cl [00105]
SO.sub.2CH.sub.3 [00106]
CH.sub.3 H H H H H 1-75 Cl [00107]
SO.sub.2CH.sub.3 CH.sub.3 [00108]
H H H H H 1-76 Cl [00109]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H white solid (123-125) 1-77 Cl [00110]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 Cl H Cl H H 1-78 Cl [00111]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H 1-79 Cl [00112]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H NO.sub.2 H H 1-80 Cl [00113]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H CF.sub.3 H H 1-81 Cl [00114]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H [00115]
H H yellow solid (135-136) 1-82 Cl [00116]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00117]
H H yellow solid (87-88) 1-83 Cl [00118]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00119]
H H 1-84 Cl [00120]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00121]
H H 1-85 Cl [00122]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00123]
H H H 1-86 Cl [00124]
SO.sub.2CH.sub.3 CH.sub.3 CF.sub.3 H H H H H 1-87 Cl [00125]
SO.sub.2CH.sub.3 CH.sub.3 H H H H H H 1-88 Cl [00126]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H H H H H 1-89 Cl [00127]
SO.sub.2CH.sub.3 [00128]
CH.sub.3 H H H H H 1-90 Cl [00129]
SO.sub.2CH.sub.3 CH.sub.3 [00130]
H H H H H 1-91 Cl CH.sub.2Br SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-92 Cl CH.sub.2Br SO.sub.2CH.sub.3 [00131]
CH.sub.3 H H H H H 1-93 Cl CH.sub.2Br SO.sub.2CH.sub.3 CH.sub.3 [00132]
H H H H H 1-94 Cl [00133]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-95 Cl [00134]
SO.sub.2CH.sub.3 [00135]
CH.sub.3 H H H H H 1-96 Cl [00136]
SO.sub.2CH.sub.3 CH.sub.3 [00137]
H H H H H 1-97 Cl [00138]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-98 Cl [00139]
SO.sub.2CH.sub.3 [00140]
CH.sub.3 H H H H H 1-99 Cl [00141]
SO.sub.2CH.sub.3 CH.sub.3 [00142]
H H H H H 1-100 Cl [00143]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-101 Cl [00144]
SO.sub.2CH.sub.3 [00145]
CH.sub.3 H H H H H 1-102 Cl [00146]
SO.sub.2CH.sub.3 CH.sub.3 [00147]
H H H H H 1-103 Cl [00148]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-104 Cl [00149]
SO.sub.2CH.sub.3 [00150]
CH.sub.3 H H H H H 1-105 Cl [00151]
SO.sub.2CH.sub.3 CH.sub.3 [00152]
H H H H H 1-106 Cl [00153]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-107 Cl [00154]
SO.sub.2CH.sub.3 [00155]
CH.sub.3 H H H H H 1-108 Cl [00156]
SO.sub.2CH.sub.3 CH.sub.3 [00157]
H H H H H 1-109 Cl [00158]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-110 Cl [00159]
SO.sub.2CH.sub.3 [00160]
CH.sub.3 H H H H H 1-111 Cl [00161]
SO.sub.2CH.sub.3 CH.sub.3 [00162]
H H H H H 1-112 Cl [00163]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-113 Cl [00164]
SO.sub.2CH.sub.3 [00165]
CH.sub.3 H H H H H 1-114 Cl [00166]
SO.sub.2CH.sub.3 CH.sub.3 [00167]
H H H H H 1-115 Cl [00168]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H pale yellow oil 1-116 Cl [00169]
SO.sub.2CH.sub.3 [00170]
CH.sub.3 H H H H H 1-117 Cl [00171]
SO.sub.2CH.sub.3 CH.sub.3 [00172]
H H H H H 1-118 Cl [00173]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-119 Cl [00174]
SO.sub.2CH.sub.3 [00175]
CH.sub.3 H H H H H 1-120 Cl [00176]
SO.sub.2CH.sub.3 CH.sub.3 [00177]
H H H H H 1-121 Cl [00178]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-122 Cl [00179]
SO.sub.2CH.sub.3 [00180]
CH.sub.3 H H H H H 1-123 Cl [00181]
SO.sub.2CH.sub.3 CH.sub.3 [00182]
H H H H H 1-124 Cl [00183]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-125 Cl [00184]
SO.sub.2CH.sub.3 [00185]
CH.sub.3 H H H H H 1-126 Cl [00186]
SO.sub.2CH.sub.3 CH.sub.3 [00187]
H H H H H 1-127 Cl [00188]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-128 Cl [00189]
SO.sub.2CH.sub.3 [00190]
CH.sub.3 H H H H H 1-129 Cl [00191]
SO.sub.2CH.sub.3 CH.sub.3 [00192]
H H H H H 1-130 Cl SO.sub.2CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-131 Cl SO.sub.2CH.sub.3 SO.sub.2CH.sub.3 [00193]
CH.sub.3 H H H H H 1-132 Cl SO.sub.2CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 [00194]
H H H H H 1-133 Cl SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-134 Cl SO.sub.2CH.sub.3 CF.sub.3 [00195]
CH.sub.3 H H H H H 1-135 Cl SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [00196]
H H H H H 1-136 Cl [00197]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-137 Cl [00198]
SO.sub.2CH.sub.3 [00199]
CH.sub.3 H H H H H 1-138 Cl [00200]
SO.sub.2CH.sub.3 CH.sub.3 [00201]
H H H H H 1-139 Cl [00202]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-140 Cl [00203]
SO.sub.2CH.sub.3 [00204]
CH.sub.3 H H H H H 1-141 Cl [00205]
SO.sub.2CH.sub.3 CH.sub.3 [00206]
H H H H H 1-142 Cl [00207]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-143 Cl [00208]
SO.sub.2CH.sub.3 [00209]
CH.sub.3 H H H H H 1-144 Cl [00210]
SO.sub.2CH.sub.3 CH.sub.3 [00211]
H H H H H 1-145 Cl [00212]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-146 Cl [00213]
SO.sub.2CH.sub.3 [00214]
CH.sub.3 H H H H H 1-147 Cl [00215]
SO.sub.2CH.sub.3 CH.sub.3 [00216]
H H H H H 1-148 Cl [00217]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-149 Cl [00218]
SO.sub.2CH.sub.3 [00219]
CH.sub.3 H H H H H 1-150 Cl [00220]
SO.sub.2CH.sub.3 CH.sub.3 [00221]
H H H H H 1-151 Cl [00222]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-152 Cl [00223]
SO.sub.2CH.sub.3 [00224]
CH.sub.3 H H H H H 1-153 Cl [00225]
SO.sub.2CH.sub.3 CH.sub.3 [00226]
H H H H H 1-154 Cl [00227]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-155 Cl [00228]
SO.sub.2CH.sub.3 [00229]
CH.sub.3 H H H H H 1-156 Cl [00230]
SO.sub.2CH.sub.3 CH.sub.3 [00231]
H H H H H 1-157 Cl [00232]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-158 Cl [00233]
SO.sub.2CH.sub.3 [00234]
CH.sub.3 H H H H H 1-159 Cl [00235]
SO.sub.2CH.sub.3 CH.sub.3 [00236]
H H H H H 1-160 Cl [00237]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-161 Cl [00238]
SO.sub.2CH.sub.3 [00239]
CH.sub.3 H H H H H 1-162 Cl [00240]
SO.sub.2CH.sub.3 CH.sub.3 [00241]
H H H H H 1-163 Cl [00242]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-164 Cl [00243]
SO.sub.2CH.sub.3 [00244]
CH.sub.3 H H H H H 1-165 Cl [00245]
SO.sub.2CH.sub.3 CH.sub.3 [00246]
H H H H H 1-166 Cl [00247]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-167 Cl [00248]
SO.sub.2CH.sub.3 [00249]
CH.sub.3 H H H H H 1-168 Cl [00250]
SO.sub.2CH.sub.3 CH.sub.3 [00251]
H H H H H 1-169 Cl [00252]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-170 Cl [00253]
SO.sub.2CH.sub.3 [00254]
CH.sub.3 H H H H H 1-171 Cl [00255]
SO.sub.2CH.sub.3 CH.sub.3 [00256]
H H H H H 1-172 Cl [00257]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-173 Cl [00258]
SO.sub.2CH.sub.3 [00259]
CH.sub.3 H H H H H 1-174 Cl [00260]
SO.sub.2CH.sub.3 CH.sub.3 [00261]
H H H H H 1-175 Cl [00262]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-176 Cl [00263]
SO.sub.2CH.sub.3 [00264]
CH.sub.3 H H H H H 1-177 Cl [00265]
SO.sub.2CH.sub.3 CH.sub.3 [00266]
H H H H H 1-178 Cl [00267]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-179 Cl [00268]
SO.sub.2CH.sub.3 [00269]
CH.sub.3 H H H H H 1-180 Cl [00270]
SO.sub.2CH.sub.3 CH.sub.3 [00271]
H H H H H 1-181 Cl [00272]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-182 Cl [00273]
SO.sub.2CH.sub.3 [00274]
CH.sub.3 H H H H H 1-183 Cl [00275]
SO.sub.2CH.sub.3 CH.sub.3 [00276]
H H H H H 1-184 Cl [00277]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-185 Cl [00278]
SO.sub.2CH.sub.3 [00279]
CH.sub.3 H H H H H 1-186 Cl [00280]
SO.sub.2CH.sub.3 CH.sub.3 [00281]
H H H H H 1-187 Cl [00282]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-188 Cl [00283]
SO.sub.2CH.sub.3 [00284]
CH.sub.3 H H H H H 1-189 Cl [00285]
SO.sub.2CH.sub.3 CH.sub.3 [00286]
H H H H H 1-190 Cl [00287]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-191 Cl [00288]
SO.sub.2CH.sub.3 [00289]
CH.sub.3 H H H H H 1-192 Cl [00290]
SO.sub.2CH.sub.3 CH.sub.3 [00291]
H H H H H 1-193 Cl [00292]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-194 Cl [00293]
SO.sub.2CH.sub.3 [00294]
CH.sub.3 H H H H H 1-195 Cl [00295]
SO.sub.2CH.sub.3 CH.sub.3 [00296]
H H H H H 1-196 Cl CN SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-197 Cl CN SO.sub.2CH.sub.3 [00297]
CH.sub.3 H H H H H 1-198 Cl CN SO.sub.2CH.sub.3 CH.sub.3 [00298]
H H H H H 1-199 Cl NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-200 Cl NO.sub.2 SO.sub.2CH.sub.3 [00299]
CH.sub.3 H H H H H 1-201 Cl NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 [00300]
H H H H H 1-202 Cl [00301]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-203 Cl [00302]
SO.sub.2CH.sub.3 [00303]
CH.sub.3 H H H H H 1-204 Cl [00304]
SO.sub.2CH.sub.3 CH.sub.3 [00305]
H H H H H 1-205 Cl [00306]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-206 Cl [00307]
SO.sub.2CH.sub.3 [00308]
CH.sub.3 H H H H H 1-207 Cl [00309]
SO.sub.2CH.sub.3 CH.sub.3 [00310]
H H H H H 1-208 Cl [00311]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-209 Cl [00312]
SO.sub.2CH.sub.3 [00313]
CH.sub.3 H H H H H 1-210 Cl [00314]
SO.sub.2CH.sub.3 CH.sub.3 [00315]
H H H H H 1-211 Cl [00316]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-212 Cl [00317]
SO.sub.2CH.sub.3 [00318]
CH.sub.3 H H H H H 1-213 Cl [00319]
SO.sub.2CH.sub.3 CH.sub.3 [00320]
H H H H H 1-214 Cl [00321]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-215 Cl [00322]
SO.sub.2CH.sub.3 [00323]
CH.sub.3 H H H H H 1-216 Cl [00324]
SO.sub.2CH.sub.3 CH.sub.3 [00325]
H H H H H 1-217 Cl [00326]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-218 Cl [00327]
SO.sub.2CH.sub.3 [00328]
CH.sub.3 H H H H H 1-219 Cl [00329]
SO.sub.2CH.sub.3 CH.sub.3 [00330]
H H H H H 1-220 Cl [00331]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-221 Cl [00332]
SO.sub.2CH.sub.3 [00333]
CH.sub.3 H H H H H 1-222 Cl [00334]
SO.sub.2CH.sub.3 CH.sub.3 [00335]
H H H H H 1-223 Cl H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H white solid (150-152) 1-224 Cl H SO.sub.2CH.sub.3 [00336]
CH.sub.3 H H H H H 1-225 Cl H SO.sub.2CH.sub.3 CH.sub.3 [00337]
H H H H H 1-226 Cl H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00338]
H H pale yellow solid (185-187) 1-227 Cl H SO.sub.2CH.sub.3 [00339]
CH.sub.3 H [00340]
H H 1-228 Cl H SO.sub.2CH.sub.3 CH.sub.3 [00341]
H [00342]
H H 1-229 Cl H Cl CH.sub.3 CH.sub.3 H H H H H pale yellow solid (95-97) 1-230 Cl H Cl [00343]
CH.sub.3 H H H H H 1-231 Cl H Cl CH.sub.3 [00344]
H H H H H 1-232 Cl H Cl CH.sub.3 CH.sub.3 H [00345]
H H pale yellow solid (114-116) 1-233 Cl H Cl [00346]
CH.sub.3 H [00347]
H H 1-234 Cl H Cl CH.sub.3 [00348]
H [00349]
H H 1-235 NO.sub.2 H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H orange solid (196-198) 1-236 NO.sub.2 H SO.sub.2CH.sub.3 [00350]
CH.sub.3 H H H H H 1-237 NO.sub.2 H SO.sub.2CH.sub.3 CH.sub.3 [00351]
H H H H H 1-238 NO.sub.2 H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00352]
H H yellow solid (173-175) 1-239 NO.sub.2 H SO.sub.2CH.sub.3 [00353]
CH.sub.3 H [00354]
H H 1-240 NO.sub.2 H SO.sub.2CH.sub.3 CH.sub.3 [00355]
H [00356]
H H 1-241 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-242 Cl Cl SO.sub.2CH.sub.3 [00357]
CH.sub.3 H H H H H 1-243 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 [00358]
H H H H H 1-244 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00359]
H H 1-245 Cl Cl SO.sub.2CH.sub.3 [00360]
CH.sub.3 H [00361]
H H 1-246 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 [00362]
H [00363]
H H 1-247 Cl [00364]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-248 Cl [00365]
SO.sub.2CH.sub.3 [00366]
CH.sub.3 H H H H H 1-249 Cl [00367]
SO.sub.2CH.sub.3 CH.sub.3 [00368]
H H H H H 1-250 Cl [00369]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00370]
H H 1-251 Cl [00371]
SO.sub.2CH.sub.3 [00372]
CH.sub.3 H [00373]
H H 1-252 Cl [00374]
SO.sub.2CH.sub.3 CH.sub.3 [00375]
H [00376]
H H 1-253 Cl [00377]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H 1-254 Cl [00378]
SO.sub.2CH.sub.3 [00379]
CH.sub.3 H H H H 1-255 Cl [00380]
SO.sub.2CH.sub.3 CH.sub.3 [00381]
H H H H 1-256 Cl [00382]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H 1-257 Cl [00383]
SO.sub.2CH.sub.3 [00384]
CH.sub.3 H H H H 1-258 Cl [00385]
SO.sub.2CH.sub.3 CH.sub.3 [00386]
H H H H 1-259 CH.sub.3 [00387]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H pale yellow solid (70-72) 1-260 CH.sub.3 [00388]
SO.sub.2CH.sub.3 [00389]
CH.sub.3 H H H H H 1-261 SO.sub.2CH.sub.3 [00390]
SO.sub.2CH.sub.3 CH.sub.3 [00391]
H H H H H 1-262 CH.sub.3 [00392]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [00393]
H H pale yellow solid (134-136) 1-263 CH.sub.3 [00394]
SO.sub.2CH.sub.3 [00395]
CH.sub.3 H [00396]
H H 1-264 CH.sub.3 [00397]
SO.sub.2CH.sub.3 CH.sub.3 [00398]
H [00399]
H H 1-265 CH.sub.3 [00400]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H white solid (187-188) 1-266 CH.sub.3 [00401]
SO.sub.2CH.sub.3 [00402]
CH.sub.3 H H H H H 1-267 CH.sub.3 [00403]
SO.sub.2CH.sub.3 CH.sub.3 [00404]
H H H H H 1-268 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H white solid (191-193) 1-269 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 [00405]
CH.sub.3 H H H H H 1-270 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 [00406]
H H H H H 1-271 CH.sub.3 CH.sub.2Br SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-272 CH.sub.3 CH.sub.2Br SO.sub.2CH.sub.3 [00407]
CH.sub.3 H H H H H 1-273 CH.sub.3 CH.sub.2Br SO.sub.2CH.sub.3 CH.sub.3 [00408]
H H H H H 1-274 CH.sub.3 F SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-275 CH.sub.3 F SO.sub.2CH.sub.3 [00409]
CH.sub.3 H H H H H 1-276 CH.sub.3 F SO.sub.2CH.sub.3 CH.sub.3 [00410]
H H H H H 1-277 CH.sub.3 Br SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-278 CH.sub.3 Br SO.sub.2CH.sub.3 [00411]
CH.sub.3 H H H H H 1-279 CH.sub.3 Br SO.sub.2CH.sub.3 CH.sub.3 [00412]
H H H H H 1-280 CH.sub.3 [00413]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H pale yellow solid (152-154) 1-281 CH.sub.3 [00414]
SO.sub.2CH.sub.3 [00415]
CH.sub.3 H H H H H 1-282 CH.sub.3 [00416]
SO.sub.2CH.sub.3 CH.sub.3 [00417]
H H H H H 1-283 CH.sub.3 [00418]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-284 CH.sub.3 [00419]
SO.sub.2CH.sub.3 [00420]
CH.sub.3 H H H H H 1-285 CH.sub.3 [00421]
SO.sub.2CH.sub.3 CH.sub.3 [00422]
H H H H H 1-286 CH.sub.3 [00423]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-287 CH.sub.3 [00424]
SO.sub.2CH.sub.3 [00425]
CH.sub.3 H H H H H I 1-288 CH.sub.3 [00426]
SO.sub.2CH.sub.3 CH.sub.3 [00427]
H H H H H 1-289 CH.sub.3 [00428]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-290 CH.sub.3 [00429]
SO.sub.2CH.sub.3 [00430]
CH.sub.3 H H H H H 1-291 CH.sub.3 [00431]
SO.sub.2CH.sub.3 CH.sub.3 [00432]
H H H H H 1-292 CH.sub.3 [00433]
SO.sub.2CH.sub.3 CH.sub.3 H H H H H H off- white solid (118-120) 1-293 CH.sub.3 [00434]
SO.sub.2CH.sub.3 [00435]
CH, H H H H H 1-294 CH.sub.3 [00436]
SO.sub.2CH.sub.3 CH.sub.3 [00437]
H H H H H 1-295 CN [00438]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-296 CN [00439]
SO.sub.2CH.sub.3 [00440]
CH.sub.3 H H H H H 1-297 CN [00441]
SO.sub.2CH.sub.3 CH.sub.3 [00442]
H H H H H 1-298 CF.sub.3 [00443]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-299 CF.sub.3 [00444]
SO.sub.2CH.sub.3 [00445]
CH.sub.3 H H H H H 1-300 CF.sub.3 [00446]
SO.sub.2CH.sub.3 CH.sub.3 [00447]
H H H H H 1-301 [00448]
[00449]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-302 [00450]
[00451]
SO.sub.2CH.sub.3 [00452]
CH.sub.3 H H H H H 1-303 [00453]
[00454]
SO.sub.2CH.sub.3 CH.sub.3 [00455]
H H H H H 1-304 [00456]
[00457]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-305 [00458]
[00459]
SO.sub.2CH.sub.3 [00460]
CH.sub.3 H H H H H 1-306 [00461]
[00462]
SO.sub.2CH.sub.3 CH.sub.3 [00463]
H H H H H 1-307 [00464]
[00465]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-308 [00466]
[00467]
SO.sub.2CH.sub.3 [00468]
CH.sub.3 H H H H H 1-309 [00469]
[00470]
SO.sub.2CH.sub.3 CH.sub.3 [00471]
H H H H H 1-310 [00472]
[00473]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-311 [00474]
[00475]
SO.sub.2CH.sub.3 [00476]
CH.sub.3 H H H H H 1-312 [00477]
[00478]
SO.sub.2CH.sub.3 CH.sub.3 [00479]
H H H H H 1-313 [00480]
[00481]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-314 [00482]
[00483]
SO.sub.2CH.sub.3 [00484]
CH.sub.3 H H H H H 1-315 [00485]
[00486]
SO.sub.2CH.sub.3 CH.sub.3 [00487]
H H H H H 1-316 [00488]
[00489]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-317 [00490]
[00491]
SO.sub.2CH.sub.3 [00492]
CH.sub.3 H H H H H 1-318 [00493]
[00494]
SO.sub.2CH.sub.3 CH.sub.3 [00495]
H H H H H 1-319 [00496]
[00497]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-320 [00498]
[00499]
SO.sub.2CH.sub.3 [00500]
CH.sub.3 H H H H H 1-321 [00501]
[00502]
SO.sub.2CH.sub.3 CH.sub.3 [00503]
H H H H H 1-322 SO.sub.2CH═CH, [00504]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-323 SO.sub.2CH═CH, [00505]
SO.sub.2CH.sub.3 [00506]
CH.sub.3 H H H H H 1-324 SO.sub.2CH═CH [00507]
SO.sub.2CH.sub.3 CH.sub.3 [00508]
H H H H H 1-325 [00509]
[00510]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-326 [00511]
[00512]
SO.sub.2CH.sub.3 [00513]
CH.sub.3 H H H H H 1-327 [00514]
[00515]
SO.sub.2CH.sub.3 CH.sub.3 [00516]
H H H H H 1-328 [00517]
[00518]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-329 [00519]
[00520]
SO.sub.2CH.sub.3 [00521]
CH.sub.3 H H H H H 1-330 [00522]
[00523]
SO.sub.2CH.sub.3 CH.sub.3 [00524]
H H H H H 1-331 [00525]
[00526]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-332 [00527]
[00528]
SO.sub.2CH.sub.3 [00529]
CH.sub.3 H H H H H 1-333 [00530]
[00531]
SO.sub.2CH.sub.3 CH.sub.3 [00532]
H H H H H 1-334 [00533]
[00534]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-335 [00535]
[00536]
SO.sub.2CH.sub.3 [00537]
CH.sub.3 H H H H H 1-336 [00538]
[00539]
SO.sub.2CH.sub.3 CH.sub.3 [00540]
H H H H H 1-337 [00541]
[00542]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-338 [00543]
[00544]
SO.sub.2CH.sub.3 [00545]
CH.sub.3 H H H H H 1-339 [00546]
[00547]
SO.sub.2CH.sub.3 CH.sub.3 [00548]
H H H H H 1-340 [00549]
[00550]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-341 [00551]
[00552]
SO.sub.2CH.sub.3 [00553]
CH.sub.3 H H H H H 1-342 [00554]
[00555]
SO.sub.2CH.sub.3 CH.sub.3 [00556]
H H H H H 1-343 [00557]
[00558]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-344 [00559]
[00560]
SO.sub.2CH.sub.3 [00561]
CH.sub.3 H H H H H 1-345 [00562]
[00563]
SO.sub.2CH.sub.3 CH.sub.3 [00564]
H H H H H 1-346 CH.sub.3 [00565]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H white solid (135-137) 1-347 CH.sub.3 [00566]
SO.sub.2CH.sub.3 [00567]
CH.sub.3 H H H H H 1-348 CH.sub.3 [00568]
SO.sub.2CH.sub.3 CH.sub.3 [00569]
H H H H H 1-349 CH.sub.3 [00570]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H yellow oil 1-350 CH.sub.3 [00571]
SO.sub.2CH.sub.3 [00572]
CH.sub.3 H H H H H 1-351 CH.sub.3 [00573]
SO.sub.2CH.sub.3 CH.sub.3 [00574]
H H H H H 1-352 CH.sub.3 [00575]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-353 CH.sub.3 [00576]
SO.sub.2CH.sub.3 [00577]
CH.sub.3 H H H H H 1-354 CH.sub.3 [00578]
SO.sub.2CH.sub.3 CH.sub.3 [00579]
H H H H H 1-355 CH.sub.3 [00580]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-356 CH.sub.3 [00581]
SO.sub.2CH.sub.3 [00582]
CH.sub.3 H H H H H 1-357 CH.sub.3 [00583]
SO.sub.2CH.sub.3 CH.sub.3 [00584]
H H H H H 1-358 CH.sub.3 [00585]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-359 CH.sub.3 [00586]
SO.sub.2CH.sub.3 [00587]
CH.sub.3 H H H H H 1-360 CH.sub.3 [00588]
SO.sub.2CH.sub.3 CH.sub.3 [00589]
H H H H H 1-361 CH.sub.3 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-362 CH.sub.3 SO.sub.2CH.sub.3 CF.sub.3 [00590]
CH.sub.3 H H H H H 1-363 CH.sub.3 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [00591]
H H H H H 1-364 CH.sub.3 [00592]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 1-365 CH.sub.3 [00593]
SO.sub.2CH.sub.3 [00594]
CH.sub.3 H H H H H 1-366 CH.sub.3 [00595]
SO.sub.2CH.sub.3 CH.sub.3 [00596]
H H H H H 1-367 NO.sub.2 H Cl CH.sub.3 CH.sub.3 H H H H H orange solid (107-109) 1-368 NO.sub.2 H Cl [00597]
CH.sub.3 H H H H H 1-369 NO.sub.2 H Cl CH.sub.3 [00598]
H H H H H 1-370 CH.sub.3 [00599]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H yellow oil 1-371 SO.sub.2CH.sub.3 H Cl CH.sub.3 CH.sub.3 H H H H H white solid (153-154) 1-372 CH.sub.3 [00600]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H H H H H H yellow oil 1-373 Cl [00601]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H yellow oil 1-374 Cl [00602]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H yellow oil 1-375 Cl [00603]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H yellow oil 1-376 Cl [00604]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H pale yellow oil 1-377 Cl [00605]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H pale yellow oil
[0118] In the compound of the formula I, W is CX.sub.2.
##STR00606##
TABLE-US-00002 TABLE 2 Structures and Physical Properties of Part of Compounds of Formula I Appearance Com- (Melting pound X.sub.1 X.sub.2 X.sub.3 Z.sub.1 Z.sub.2 Q Point ° C.) 2-1 CH.sub.3 [00607]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00608]
white solid (170-171) 2-2 CH.sub.3 [00609]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00610]
2-3 CH.sub.3 [00611]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00612]
2-4 CH.sub.3 [00613]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00614]
2-5 CH.sub.3 [00615]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00616]
2-6 CH.sub.3 [00617]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00618]
2-7 CH.sub.3 [00619]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00620]
2-8 CH.sub.3 [00621]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00622]
2-9 CH.sub.3 [00623]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00624]
2-10 CH.sub.3 [00625]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00626]
2-11 CH.sub.3 [00627]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00628]
2-12 CH.sub.3 [00629]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00630]
2-13 CH.sub.3 [00631]
SO.sub.2CH.sub.3 CH.sub.3 H [00632]
2-14 CH.sub.3 [00633]
SO.sub.2CH.sub.3 CH.sub.3 H [00634]
2-15 CH.sub.3 [00635]
SO.sub.2CH.sub.3 CH.sub.3 H [00636]
2-16 CH.sub.3 [00637]
SO.sub.2CH.sub.3 CH.sub.3 H [00638]
2-17 CH.sub.3 [00639]
SO.sub.2CH.sub.3 CH.sub.3 H [00640]
2-18 CH.sub.3 [00641]
SO.sub.2CH.sub.3 CH.sub.3 H [00642]
2-19 CH.sub.3 [00643]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00644]
white solid (164-165) 2-20 CH.sub.3 [00645]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00646]
2-21 CH.sub.3 [00647]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00648]
2-22 CH.sub.3 [00649]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00650]
2-23 CH.sub.3 [00651]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00652]
2-24 CH.sub.3 [00653]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00654]
2-25 CH.sub.3 [00655]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00656]
2-26 CH.sub.3 [00657]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00658]
2-27 CH.sub.3 [00659]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00660]
2-28 CH.sub.3 [00661]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00662]
2-29 CH.sub.3 [00663]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00664]
2-30 CH.sub.3 [00665]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00666]
2-31 CH.sub.3 [00667]
SO.sub.2CH.sub.3 CH.sub.3 H [00668]
2-32 CH.sub.3 [00669]
SO.sub.2CH.sub.3 CH.sub.3 H [00670]
2-33 CH.sub.3 [00671]
SO.sub.2CH.sub.3 CH.sub.3 H [00672]
2-34 CH.sub.3 [00673]
SO.sub.2CH.sub.3 CH.sub.3 H [00674]
2-35 CH.sub.3 [00675]
SO.sub.2CH.sub.3 CH.sub.3 H [00676]
2-36 CH.sub.3 [00677]
SO.sub.2CH.sub.3 CH.sub.3 H [00678]
2-37 CH.sub.3 [00679]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00680]
white solid (157-158) 2-38 CH.sub.3 [00681]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00682]
2-39 CH.sub.3 [00683]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00684]
2-40 CH.sub.3 [00685]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00686]
2-41 CH.sub.3 [00687]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00688]
2-42 CH.sub.3 [00689]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00690]
2-43 CH.sub.3 [00691]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00692]
2-44 CH.sub.3 [00693]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00694]
2-45 CH.sub.3 [00695]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00696]
2-46 CH.sub.3 [00697]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00698]
2-47 CH.sub.3 [00699]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00700]
2-48 CH.sub.3 [00701]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00702]
2-49 CH.sub.3 [00703]
SO.sub.2CH.sub.3 CH.sub.3 H [00704]
2-50 CH.sub.3 [00705]
SO.sub.2CH.sub.3 CH.sub.3 H [00706]
2-51 CH.sub.3 [00707]
SO.sub.2CH.sub.3 CH.sub.3 H [00708]
2-52 CH.sub.3 [00709]
SO.sub.2CH.sub.3 CH.sub.3 H [00710]
2-53 CH.sub.3 [00711]
SO.sub.2CH.sub.3 CH.sub.3 H [00712]
2-54 CH.sub.3 [00713]
SO.sub.2CH.sub.3 CH.sub.3 H [00714]
2-55 CH.sub.3 [00715]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00716]
yellow oil 2-56 CH.sub.3 [00717]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00718]
2-57 CH.sub.3 [00719]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00720]
pale yellow solid (134-136) 2-58 CH.sub.3 [00721]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00722]
2-59 CH.sub.3 [00723]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00724]
2-60 CH.sub.3 [00725]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00726]
2-61 CH.sub.3 [00727]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00728]
yellow oil 2-62 CH.sub.3 [00729]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00730]
2-63 CH.sub.3 [00731]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00732]
yellow oil 2-64 CH.sub.3 [00733]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00734]
2-65 CH.sub.3 [00735]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00736]
2-66 CH.sub.3 [00737]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00738]
2-67 CH.sub.3 [00739]
SO.sub.2CH.sub.3 CH.sub.3 H [00740]
yellow oil 2-68 CH.sub.3 [00741]
SO.sub.2CH.sub.3 CH.sub.3 H [00742]
2-69 CH.sub.3 [00743]
SO.sub.2CH.sub.3 CH.sub.3 H [00744]
2-70 CH.sub.3 [00745]
SO.sub.2CH.sub.3 CH.sub.3 H [00746]
2-71 CH.sub.3 [00747]
SO.sub.2CH.sub.3 CH.sub.3 H [00748]
2-72 CH.sub.3 [00749]
SO.sub.2CH.sub.3 CH.sub.3 H [00750]
2-73 CH.sub.3 [00751]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00752]
brown oil 2-74 CH.sub.3 [00753]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00754]
2-75 CH.sub.3 [00755]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00756]
2-76 CH.sub.3 [00757]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00758]
2-77 CH.sub.3 [00759]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00760]
2-78 CH.sub.3 [00761]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00762]
2-79 CH.sub.3 [00763]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00764]
2-80 CH.sub.3 [00765]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00766]
2-81 CH.sub.3 [00767]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00768]
2-82 CH.sub.3 [00769]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00770]
2-83 CH.sub.3 [00771]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00772]
2-84 CH.sub.3 [00773]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00774]
2-85 CH.sub.3 [00775]
SO.sub.2CH.sub.3 CH.sub.3 H [00776]
2-86 CH.sub.3 [00777]
SO.sub.2CH.sub.3 CH.sub.3 H [00778]
2-87 CH.sub.3 [00779]
SO.sub.2CH.sub.3 CH.sub.3 H [00780]
2-88 CH.sub.3 [00781]
SO.sub.2CH.sub.3 CH.sub.3 H [00782]
2-89 CH.sub.3 [00783]
SO.sub.2CH.sub.3 CH.sub.3 H [00784]
2-90 CH.sub.3 [00785]
SO.sub.2CH.sub.3 CH.sub.3 H [00786]
2-91 CH.sub.3 [00787]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00788]
2-92 CH.sub.3 [00789]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00790]
2-93 CH.sub.3 [00791]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00792]
2-94 CH.sub.3 [00793]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00794]
2-95 CH.sub.3 [00795]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00796]
2-96 CH.sub.3 [00797]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00798]
2-97 CH.sub.3 [00799]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00800]
2-98 CH.sub.3 [00801]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00802]
2-99 CH.sub.3 [00803]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00804]
2-100 CH.sub.3 [00805]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00806]
2-101 CH.sub.3 [00807]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00808]
2-102 CH.sub.3 [00809]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00810]
2-103 CH.sub.3 [00811]
SO.sub.2CH.sub.3 CH.sub.3 H [00812]
2-104 CH.sub.3 [00813]
SO.sub.2CH.sub.3 CH.sub.3 H [00814]
2-105 CH.sub.3 [00815]
SO.sub.2CH.sub.3 CH.sub.3 H [00816]
2-106 CH.sub.3 [00817]
SO.sub.2CH.sub.3 CH.sub.3 H [00818]
2-107 CH.sub.3 [00819]
SO.sub.2CH.sub.3 CH.sub.3 H [00820]
2-108 CH.sub.3 [00821]
SO.sub.2CH.sub.3 CH.sub.3 H [00822]
2-109 CH.sub.3 [00823]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00824]
2-110 CH.sub.3 [00825]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00826]
2-111 CH.sub.3 [00827]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00828]
2-112 CH.sub.3 [00829]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00830]
2-113 CH.sub.3 [00831]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00832]
2-114 CH.sub.3 [00833]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00834]
2-115 CH.sub.3 [00835]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00836]
2-116 CH.sub.3 [00837]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00838]
2-117 CH.sub.3 [00839]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00840]
2-118 CH.sub.3 [00841]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00842]
2-119 CH.sub.3 [00843]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00844]
2-120 CH.sub.3 [00845]
SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00846]
2-121 CH.sub.3 [00847]
SO.sub.2CH.sub.3 CH.sub.3 H [00848]
white solid (209-210) 2-122 CH.sub.3 [00849]
SO.sub.2CH.sub.3 CH.sub.3 H [00850]
2-123 CH.sub.3 [00851]
SO.sub.2CH.sub.3 CH.sub.3 H [00852]
white solid (199-200) 2-124 CH.sub.3 [00853]
SO.sub.2CH.sub.3 CH.sub.3 H [00854]
2-125 CH.sub.3 [00855]
SO.sub.2CH.sub.3 CH.sub.3 H [00856]
2-126 CH.sub.3 [00857]
SO.sub.2CH.sub.3 CH.sub.3 H [00858]
2-127 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00859]
white solid (186-188) 2-128 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00860]
2-129 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00861]
2-130 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00862]
2-131 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00863]
2-132 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00864]
2-133 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00865]
2-134 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00866]
2-135 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00867]
2-136 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00868]
2-137 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00869]
2-138 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3CH.sub.2 H [00870]
2-139 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [00871]
2-140 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [00872]
2-141 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [00873]
2-142 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [00874]
2-143 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [00875]
2-144 CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [00876]
2-145 CH.sub.3 [00877]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00878]
white solid (116-118) 2-146 CH.sub.3 [00879]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00880]
2-147 CH.sub.3 [00881]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00882]
2-148 CH.sub.3 [00883]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00884]
2-149 CH.sub.3 [00885]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00886]
2-150 CH.sub.3 [00887]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00888]
2-151 CH.sub.3 [00889]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00890]
2-152 CH.sub.3 [00891]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00892]
2-153 CH.sub.3 [00893]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00894]
2-154 CH.sub.3 [00895]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00896]
2-155 CH.sub.3 [00897]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00898]
2-156 CH.sub.3 [00899]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00900]
2-157 CH.sub.3 [00901]
SO.sub.2CH.sub.3 CH.sub.3 H [00902]
2-158 CH.sub.3 [00903]
SO.sub.2CH.sub.3 CH.sub.3 H [00904]
2-159 CH.sub.3 [00905]
SO.sub.2CH.sub.3 CH.sub.3 H [00906]
2-160 CH.sub.3 [00907]
SO.sub.2CH.sub.3 CH.sub.3 H [00908]
2-161 CH.sub.3 [00909]
SO.sub.2CH.sub.3 CH.sub.3 H [00910]
2-162 CH.sub.3 [00911]
SO.sub.2CH.sub.3 CH.sub.3 H [00912]
2-163 Cl [00913]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00914]
2-164 Cl [00915]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00916]
2-165 Cl [00917]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00918]
2-166 Cl [00919]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00920]
2-167 Cl [00921]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00922]
2-168 Cl [00923]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00924]
2-169 Cl [00925]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00926]
2-170 Cl [00927]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00928]
2-171 Cl [00929]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00930]
2-172 Cl [00931]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00932]
2-173 Cl [00933]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00934]
2-174 Cl [00935]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00936]
2-175 Cl [00937]
SO.sub.2CH.sub.3 CH.sub.3 H [00938]
2-176 Cl [00939]
SO.sub.2CH.sub.3 CH.sub.3 H [00940]
2-177 Cl [00941]
SO.sub.2CH.sub.3 CH.sub.3 H [00942]
2-178 Cl [00943]
SO.sub.2CH.sub.3 CH.sub.3 H [00944]
2-179 Cl [00945]
SO.sub.2CH.sub.3 CH.sub.3 H [00946]
2-180 Cl [00947]
SO.sub.2CH.sub.3 CH.sub.3 H [00948]
2-181 Cl [00949]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00950]
2-182 Cl [00951]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00952]
2-183 Cl [00953]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00954]
2-184 Cl [00955]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00956]
2-185 Cl [00957]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00958]
2-186 Cl [00959]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00960]
2-187 Cl [00961]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00962]
2-188 Cl [00963]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00964]
2-189 Cl [00965]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00966]
2-190 Cl [00967]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00968]
2-191 Cl [00969]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00970]
2-192 Cl [00971]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00972]
2-193 Cl [00973]
SO.sub.2CH.sub.3 CH.sub.3 H [00974]
2-194 Cl [00975]
SO.sub.2CH.sub.3 CH.sub.3 H [00976]
2-195 Cl [00977]
SO.sub.2CH.sub.3 CH.sub.3 H [00978]
2-196 Cl [00979]
SO.sub.2CH.sub.3 CH.sub.3 H [00980]
2-197 Cl [00981]
SO.sub.2CH.sub.3 CH.sub.3 H [00982]
2-198 Cl [00983]
SO.sub.2CH.sub.3 CH.sub.3 H [00984]
2-199 Cl [00985]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00986]
2-200 Cl [00987]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00988]
2-201 Cl [00989]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00990]
2-202 Cl [00991]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00992]
2-203 Cl [00993]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00994]
2-204 Cl [00995]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [00996]
2-205 Cl [00997]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [00998]
2-206 Cl [00999]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01000]
2-207 Cl [01001]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01002]
2-208 Cl [01003]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01004]
2-209 Cl [01005]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01006]
2-210 Cl [01007]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01008]
2-211 Cl [01009]
SO.sub.2CH.sub.3 CH.sub.3 H [01010]
2-212 Cl [01011]
SO.sub.2CH.sub.3 CH.sub.3 H [01012]
2-213 Cl [01013]
SO.sub.2CH.sub.3 CH.sub.3 H [01014]
2-214 Cl [01015]
SO.sub.2CH.sub.3 CH.sub.3 H [01016]
2-215 Cl [01017]
SO.sub.2CH.sub.3 CH.sub.3 H [01018]
2-216 Cl [01019]
SO.sub.2CH.sub.3 CH.sub.3 H [01020]
2-217 Cl [01021]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01022]
2-218 Cl [01023]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01024]
2-219 Cl [01025]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01026]
2-220 Cl [01027]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01028]
2-221 Cl [01029]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01030]
2-222 Cl [01031]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01032]
2-223 Cl [01033]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01034]
2-224 Cl [01035]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01036]
2-225 Cl [01037]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01038]
2-226 Cl [01039]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01040]
2-227 Cl [01041]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01042]
2-228 Cl [01043]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01044]
2-229 Cl [01045]
SO.sub.2CH.sub.3 CH.sub.3 H [01046]
2-230 Cl [01047]
SO.sub.2CH.sub.3 CH.sub.3 H [01048]
2-231 Cl [01049]
SO.sub.2CH.sub.3 CH.sub.3 H [01050]
2-232 Cl [01051]
SO.sub.2CH.sub.3 CH.sub.3 H [01052]
2-233 Cl [01053]
SO.sub.2CH.sub.3 CH.sub.3 H [01054]
2-234 Cl [01055]
SO.sub.2CH.sub.3 CH.sub.3 H [01056]
2-235 Cl [01057]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01058]
2-236 Cl [01059]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01060]
2-237 Cl [01061]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01062]
2-238 Cl [01063]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01064]
2-239 Cl [01065]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01066]
2-240 Cl [01067]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01068]
2-241 Cl [01069]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01070]
2-242 Cl [01071]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01072]
2-243 Cl [01073]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01074]
2-244 Cl [01075]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01076]
2-245 Cl [01077]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01078]
2-246 Cl [01079]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01080]
2-247 Cl [01081]
SO.sub.2CH.sub.3 CH.sub.3 H [01082]
2-248 Cl [01083]
SO.sub.2CH.sub.3 CH.sub.3 H [01084]
2-249 Cl [01085]
SO.sub.2CH.sub.3 CH.sub.3 H [01086]
2-250 Cl [01087]
SO.sub.2CH.sub.3 CH.sub.3 H [01088]
2-251 Cl [01089]
SO.sub.2CH.sub.3 CH.sub.3 H [01090]
2-252 Cl [01091]
SO.sub.2CH.sub.3 CH.sub.3 H [01092]
2-253 Cl [01093]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01094]
2-254 Cl [01095]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01096]
2-255 Cl [01097]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01098]
2-256 Cl [01099]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01100]
2-257 Cl [01101]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01102]
2-258 Cl [01103]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01104]
2-259 Cl [01105]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01106]
2-260 Cl [01107]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01108]
2-261 Cl [01109]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01110]
2-262 Cl [01111]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01112]
2-263 Cl [01113]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01114]
2-264 Cl [01115]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01116]
2-265 Cl [01117]
SO.sub.2CH.sub.3 CH.sub.3 H [01118]
2-266 Cl [01119]
SO.sub.2CH.sub.3 CH.sub.3 H [01120]
2-267 Cl [01121]
SO.sub.2CH.sub.3 CH.sub.3 H [01122]
2-268 Cl [01123]
SO.sub.2CH.sub.3 CH.sub.3 H [01124]
2-269 Cl [01125]
SO.sub.2CH.sub.3 CH.sub.3 H [01126]
2-270 Cl [01127]
SO.sub.2CH.sub.3 CH.sub.3 H [01128]
2-271 Cl [01129]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01130]
2-272 Cl [01131]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01132]
2-273 Cl [01133]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01134]
2-274 Cl [01135]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01136]
2-275 Cl [01137]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01138]
2-276 Cl [01139]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01140]
2-277 Cl [01141]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01142]
2-278 Cl [01143]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01144]
2-279 Cl [01145]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01146]
2-280 Cl [01147]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01148]
2-281 Cl [01149]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01150]
2-282 Cl [01151]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01152]
2-283 Cl [01153]
SO.sub.2CH.sub.3 CH.sub.3 H [01154]
2-284 Cl [01155]
SO.sub.2CH.sub.3 CH.sub.3 H [01156]
2-285 Cl [01157]
SO.sub.2CH.sub.3 CH.sub.3 H [01158]
2-286 Cl [01159]
SO.sub.2CH.sub.3 CH.sub.3 H [01160]
2-287 Cl [01161]
SO.sub.2CH.sub.3 CH.sub.3 H [01162]
2-288 Cl [01163]
SO.sub.2CH.sub.3 CH.sub.3 H [01164]
2-289 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01165]
white solid (172-174) 2-290 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01166]
2-291 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01167]
white solid (137-139) 2-292 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01168]
2-293 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01169]
2-294 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01170]
2-295 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01171]
2-296 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01172]
2-297 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01173]
2-298 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01174]
2-299 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01175]
2-300 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01176]
2-301 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [01177]
2-302 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [01178]
2-303 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [01179]
2-304 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [01180]
2-305 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [01181]
2-306 Cl CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 H [01182]
2-307 Cl [01183]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01184]
white solid (181-183) 2-308 Cl [01185]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01186]
2-309 Cl [01187]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01188]
yellow solid (128-130) 2-310 Cl [01189]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01190]
2-311 Cl [01191]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01192]
2-312 Cl [01193]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01194]
2-313 Cl [01195]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01196]
2-314 Cl [01197]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01198]
2-315 Cl [01199]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01200]
2-316 Cl [01201]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01202]
2-317 Cl [01203]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01204]
2-318 Cl [01205]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01206]
2-319 Cl [01207]
SO.sub.2CH.sub.3 CH.sub.3 H [01208]
2-320 Cl [01209]
SO.sub.2CH.sub.3 CH.sub.3 H [01210]
2-321 Cl [01211]
SO.sub.2CH.sub.3 CH.sub.3 H [01212]
2-322 Cl [01213]
SO.sub.2CH.sub.3 CH.sub.3 H [01214]
2-323 Cl [01215]
SO.sub.2CH.sub.3 CH.sub.3 H [01216]
2-324 Cl [01217]
SO.sub.2CH.sub.3 CH.sub.3 H [01218]
2-325 Cl [01219]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01220]
2-326 Cl [01221]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01222]
2-327 Cl [01223]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01224]
2-328 Cl [01225]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01226]
2-329 Cl [01227]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01228]
2-330 Cl [01229]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01230]
2-331 Cl [01231]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01232]
2-332 Cl [01233]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01234]
2-333 Cl [01235]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01236]
2-334 Cl [01237]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01238]
2-335 Cl [01239]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01240]
2-336 Cl [01241]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01242]
2-337 Cl [01243]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01244]
2-338 Cl [01245]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01246]
2-339 Cl [01247]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01248]
2-340 Cl [01249]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01250]
2-341 Cl [01251]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01252]
2-342 Cl [01253]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01254]
2-343 SO.sub.2CH.sub.3 H Cl CH.sub.3 CH.sub.3 [01255]
white solid (170-171) 2-344 SO.sub.2CH.sub.3 H Cl CH.sub.3 CH.sub.3 [01256]
2-345 SO.sub.2CH.sub.3 H Cl CH.sub.3 CH.sub.3 [01257]
2-346 SO.sub.2CH.sub.3 H Cl CH.sub.3 CH.sub.3 [01258]
2-347 SO.sub.2CH.sub.3 H Cl CH.sub.3 CH.sub.3 [01259]
2-348 SO.sub.2CH.sub.3 H Cl CH.sub.3 CH.sub.3 [01260]
2-349 SO.sub.2CH.sub.3 H Cl CH.sub.2CH.sub.3 H [01261]
2-350 SO.sub.2CH.sub.3 H Cl CH.sub.2CH.sub.3 H [01262]
2-351 SO.sub.2CH.sub.3 H Cl CH.sub.2CH.sub.3 H [01263]
2-352 SO.sub.2CH.sub.3 H Cl CH.sub.2CH.sub.3 H [01264]
2-353 SO.sub.2CH.sub.3 H Cl CH.sub.2CH.sub.3 H [01265]
2-354 SO.sub.2CH.sub.3 H Cl CH.sub.2CH.sub.3 H [01266]
2-355 SO.sub.2CH.sub.3 H Cl CH.sub.3 H [01267]
2-356 SO.sub.2CH.sub.3 H Cl CH.sub.3 H [01268]
2-357 SO.sub.2CH.sub.3 H Cl CH.sub.3 H [01269]
2-358 SO.sub.2CH.sub.3 H Cl CH.sub.3 H [01270]
2-359 SO.sub.2CH.sub.3 H Cl CH.sub.3 H [01271]
2-360 SO.sub.2CH.sub.3 H Cl CH.sub.3 H [01272]
2-361 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01273]
2-362 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01274]
2-363 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01275]
2-364 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01276]
2-365 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01277]
2-366 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01278]
2-367 Cl Cl SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01279]
2-368 Cl Cl SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01280]
2-369 Cl Cl SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01281]
2-370 Cl Cl SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01282]
2-371 Cl Cl SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01283]
2-372 Cl Cl SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01284]
2-373 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 H [01285]
2-374 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 H [01286]
2-375 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 H [01287]
2-376 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 H [01288]
2-377 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 H [01289]
2-378 Cl Cl SO.sub.2CH.sub.3 CH.sub.3 H [01290]
2-379 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 [01291]
while solid (129-131) 2-380 SO.sub.2CH.sub.3 H CF.sub.3 CH.sub.3 CH.sub.3 [01292]
pale pink solid (124-126) 2-381 Cl [01293]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01294]
yellow oil 2-382 Cl [01295]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01296]
yellow oil 2-383 Cl H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01297]
yellow solid (168-170) 2-384 Cl H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01298]
pale yellow solid (136-138) 2-385 Cl H Cl CH.sub.3 CH.sub.3 [01299]
pink solid (133-135) 2-386 Cl H Cl CH.sub.3 CH.sub.3 [01300]
while solid (112-114) 2-387 NO.sub.2 H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01301]
pale yellow solid (144-146) 2-388 NO.sub.2 H SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01302]
orange solid (150-152) 2-389 Cl H NO.sub.2 CH.sub.3 CH.sub.3 [01303]
yellow oil 2-390 Cl H NO.sub.2 CH.sub.3 CH.sub.3 [01304]
yellow solid (115-117) 2-391 NO.sub.2 H Cl CH.sub.3 CH.sub.3 [01305]
pale yellow solid (128-130) 2-392 NO.sub.2 H Cl CH.sub.3 CH.sub.3 [01306]
pale yellow solid (134-136) 2-393 Cl [01307]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01308]
2-394 Cl [01309]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01310]
2-395 Cl [01311]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01312]
2-396 Cl [01313]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01314]
2-397 Cl [01315]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01316]
2-398 Cl [01317]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01318]
2-399 Cl [01319]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01320]
2-400 Cl [01321]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01322]
2-401 Cl [01323]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01324]
2-402 Cl [01325]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01326]
2-403 Cl [01327]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01328]
2-404 Cl [01329]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01330]
2-405 Cl [01331]
SO.sub.2CH.sub.3 CH.sub.3 H [01332]
2-406 Cl [01333]
SO.sub.2CH.sub.3 CH.sub.3 H [01334]
2-407 Cl [01335]
SO.sub.2CH.sub.3 CH.sub.3 H [01336]
2-408 Cl [01337]
SO.sub.2CH.sub.3 CH.sub.3 H [01338]
2-409 Cl [01339]
SO.sub.2CH.sub.3 CH.sub.3 H [01340]
2-410 Cl [01341]
SO.sub.2CH.sub.3 CH.sub.3 H [01342]
2-411 Cl CH.sub.3SO.sub.2CH.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01343]
2-412 Cl CH.sub.3SO.sub.2CH.sub.2 SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 H [01344]
2-413 Cl CH.sub.3SO.sub.2CH.sub.2 SO.sub.2CH.sub.3 CH.sub.3 H [01345]
2-414 CH.sub.3 [01346]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01347]
yellow solid (147-149) 2-415 CH.sub.3 [01348]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01349]
yellow solid (167-169) 2-416 CH.sub.3 [01350]
SO.sub.2CH.sub.3 CH.sub.3 [01351]
[01352]
yellow oil 2-417 CH.sub.3 [01353]
SO.sub.2CH.sub.3 CH.sub.3 [01354]
[01355]
yellow solid (110-111) 2-418 CH.sub.3 [01356]
SO.sub.2CH.sub.3 CH.sub.3 [01357]
[01358]
yellow solid (101-103) 2-419 CH.sub.3 [01359]
SO.sub.2CH.sub.3 CH.sub.3 [01360]
[01361]
yellow oil 2-420 CH.sub.3 [01362]
SO.sub.2CH.sub.3 CH.sub.2CH.sub.3 CH.sub.3 [01363]
yellow solid (105-106) 2-421 Cl [01364]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01365]
pink oil
[0119] In the compound of the formula I, W is N and the stereo configuration is trans.
##STR01366##
TABLE-US-00003 TABLE 3 Structures and Physical Properties of Part of Compounds of Formula I Appear- ance (Melting Com- Point pound X.sub.1 X.sub.3 Z.sub.1 Z.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 ° C.) 3-1 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-2 SO.sub.2CH.sub.3 CF.sub.3 [01367]
CH.sub.3 H H H H H 3-3 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01368]
H H H H H 3-4 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 Cl H Cl H H 3-5 SO.sub.2CH.sub.3 CF.sub.3 [01369]
CH.sub.3 Cl H Cl H H 3-6 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01370]
Cl H Cl H H 3-7 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H H OCH.sub.3 H H 3-8 SO.sub.2CH.sub.3 CF.sub.3 [01371]
CH.sub.3 H H OCH.sub.3 H H 3-9 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01372]
H H OCH.sub.3 H H 3-10 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H H NO.sub.2 H H 3-11 SO.sub.2CH.sub.3 CF.sub.3 [01373]
CH.sub.3 H H NO.sub.2 H H 3-12 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01374]
H H NO.sub.2 H H 3-13 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H H CF.sub.3 H H 3-14 SO.sub.2CH.sub.3 CF.sub.3 [01375]
CH.sub.3 H H CF.sub.3 H H 3-15 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01376]
H H CF.sub.3 H H 3-16 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H OCF.sub.3 H H H 3-17 SO.sub.2CH.sub.3 CF.sub.3 [01377]
CH.sub.3 H OCF.sub.3 H H H 3-18 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01378]
H OCF.sub.3 H H H 3-19 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H H [01379]
H H 3-20 SO.sub.2CH.sub.3 CF.sub.3 [01380]
CH.sub.3 H H [01381]
H H 3-21 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01382]
H H [01383]
H H 3-22 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H [01384]
H H 3-23 SO.sub.2CH.sub.3 CF.sub.3 [01385]
CH.sub.3 H [01386]
H H 3-24 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01387]
H [01388]
H H 3-25 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H [01389]
H H 3-26 SO.sub.2CH.sub.3 CF.sub.3 [01390]
CH.sub.3 H [01391]
H H 3-27 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01392]
H [01393]
H H 3-28 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 H [01394]
H H 3-29 SO.sub.2CH.sub.3 CF.sub.3 [01395]
CH.sub.3 H [01396]
H H 3-30 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01397]
H [01398]
H H 3-31 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01399]
H H H 3-32 SO.sub.2CH.sub.3 CF.sub.3 [01400]
CH.sub.3 [01401]
H H H 3-33 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01402]
[01403]
H H H 3-34 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-35 NO.sub.2 SO.sub.2CH.sub.3 [01404]
CH.sub.3 H H H H H 3-36 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 [01405]
H H H H H 3-37 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [01406]
H H 3-38 NO.sub.2 SO.sub.2CH.sub.3 [01407]
CH.sub.3 H [01408]
H H 3-39 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 [01409]
H [01410]
H H 3-40 NO.sub.2 Cl CH.sub.3 CH.sub.3 H H H H H 3-41 NO.sub.2 Cl [01411]
CH.sub.3 H H H H H 3-42 NO.sub.2 Cl CH.sub.3 [01412]
H H H H H 3-43 Cl Cl CH.sub.3 CH.sub.3 H H H H H 3-44 Cl Cl [01413]
CH.sub.3 H H H H H 3-45 Cl Cl CH.sub.3 [01414]
H H H H H 3-46 Cl Cl CH.sub.3 CH.sub.3 H [01415]
H H 3-47 Cl Cl [01416]
CH.sub.3 H [01417]
H H 3-48 Cl Cl CH.sub.3 [01418]
H [01419]
H H 3-49 Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-50 Cl SO.sub.2CH.sub.3 [01420]
CH.sub.3 H H H H H 3-51 Cl SO.sub.2CH.sub.3 CH.sub.3 [01421]
H H H H H 3-52 Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H [01422]
H H 3-53 Cl SO.sub.2CH.sub.3 [01423]
CH.sub.3 H [01424]
H H 3-54 Cl SO.sub.2CH.sub.3 CH.sub.3 [01425]
H [01426]
H H 3-55 CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-56 CH.sub.3 SO.sub.2CH.sub.3 [01427]
CH.sub.3 H H H H H 3-57 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 [01428]
H H H H H 3-58 CN SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-59 CN SO.sub.2CH.sub.3 [01429]
CH.sub.3 H H H H H 3-60 CN SO.sub.2CH.sub.3 CH.sub.3 [01430]
H H H H H 3-61 CF.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-62 CF.sub.3 SO.sub.2CH.sub.3 [01431]
CH.sub.3 H H H H H 3-63 CF.sub.3 SO.sub.2CH.sub.3 CH.sub.3 [01432]
H H H H H 3-64 [01433]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-65 [01434]
SO.sub.2CH.sub.3 [01435]
CH.sub.3 H H H H H 3-66 [01436]
SO.sub.2CH.sub.3 CH.sub.3 [01437]
H H H H H 3-67 [01438]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-68 [01439]
SO.sub.2CH.sub.3 [01440]
CH.sub.3 H H H H H 3-69 [01441]
SO.sub.2CH.sub.3 CH.sub.3 [01442]
H H H H H 3-70 [01443]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-71 [01444]
SO.sub.2CH.sub.3 [01445]
CH.sub.3 H H H H H 3-72 [01446]
SO.sub.2CH.sub.3 CH.sub.3 [01447]
H H H H H 3-73 [01448]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-74 [01449]
SO.sub.2CH.sub.3 [01450]
CH.sub.3 H H H H H 3-75 [01451]
SO.sub.2CH.sub.3 CH.sub.3 [01452]
H H H H H 3-76 [01453]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-77 [01454]
SO.sub.2CH.sub.3 [01455]
CH.sub.3 H H H H H 3-78 [01456]
SO.sub.2CH.sub.3 CH.sub.3 [01457]
H H H H H 3-79 [01458]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-80 [01459]
SO.sub.2CH.sub.3 [01460]
CH.sub.3 H H H H H 3-81 [01461]
SO.sub.2CH.sub.3 CH.sub.3 [01462]
H H H H H 3-82 [01463]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-83 [01464]
SO.sub.2CH.sub.3 [01465]
CH.sub.3 H H H H H 3-84 [01466]
SO.sub.2CH.sub.3 CH.sub.3 [01467]
H H H H H 3-85 SO2CH═CH.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-86 SO2CH═CH.sub.2 SO.sub.2CH.sub.3 [01468]
CH.sub.3 H H H H H 3-87 SO2CH═CH.sub.2 SO.sub.2CH.sub.3 CH.sub.3 [01469]
H H H H H 3-88 [01470]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-89 [01471]
SO.sub.2CH.sub.3 [01472]
CH.sub.3 H H H H H 3-90 [01473]
SO.sub.2CH CH.sub.3 [01474]
H H H H H 3-91 [01475]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-92 [01476]
SO.sub.2CH.sub.3 [01477]
CH.sub.3 H H H H H 3-93 [01478]
SO.sub.2CH.sub.3 CH.sub.3 [01479]
H H H H H 3-94 [01480]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-95 [01481]
SO.sub.2CH.sub.3 [01482]
CH.sub.3 H H H H H 3-96 [01483]
SO.sub.2CH CH.sub.3 [01484]
H H H H H 3-97 [01485]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-98 [01486]
SO.sub.2CH.sub.3 [01487]
CH.sub.3 H H H H H 3-99 [01488]
SO.sub.2CH.sub.3 CH.sub.3 [01489]
H H H H H 3-100 [01490]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-101 [01491]
SO.sub.2CH.sub.3 [01492]
CH.sub.3 H H H H H 3-102 [01493]
SO.sub.2CH.sub.3 CH.sub.3 [01494]
H H H H H 3-103 [01495]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-104 [01496]
SO.sub.2CH.sub.3 [01497]
CH.sub.3 H H H H H 3-105 [01498]
SO.sub.2CH.sub.3 CH.sub.3 [01499]
H H H H H 3-106 [01500]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 H H H H H 3-107 [01501]
SO.sub.2CH.sub.3 [01502]
CH.sub.3 H H H H H 3-108 [01503]
SO.sub.2CH.sub.3 CH.sub.3 [01504]
H H H H H 3-109 H Cl CH.sub.3 CH.sub.3 H H H H H white solid (115- 120)
[0120] In the compound of the formula I, W is N.
##STR01505##
TABLE-US-00004 TABLE 4 Structures and Physical Properties of Part of Compounds of Formula I Appearance (Melting Compound X.sub.1 X.sub.3 R.sub.1 R.sub.2 Z Point ° C.) 4-1 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01506]
4-2 SO.sub.2CH.sub.3 CF.sub.3 [01507]
CH.sub.3 [01508]
4-3 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01509]
[01510]
4-4 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01511]
4-5 SO.sub.2CH.sub.3 CF.sub.3 [01512]
CH.sub.3 [01513]
4-6 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01514]
[01515]
4-7 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01516]
4-8 SO.sub.2CH.sub.3 CF.sub.3 [01517]
CH.sub.3 [01518]
4-9 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01519]
[01520]
4-10 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01521]
4-11 SO.sub.2CH.sub.3 CF.sub.3 [01522]
CH.sub.3 [01523]
4-12 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01524]
[01525]
4-13 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01526]
4-14 SO.sub.2CH.sub.3 CF.sub.3 [01527]
CH.sub.3 [01528]
4-15 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01529]
[01530]
4-16 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01531]
4-17 SO.sub.2CH.sub.3 CF.sub.3 [01532]
CH.sub.3 [01533]
4-18 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01534]
[01535]
4-19 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01536]
4-20 SO.sub.2CH.sub.3 CF.sub.3 [01537]
CH.sub.3 [01538]
4-21 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01539]
[01540]
4-22 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01541]
4-23 SO.sub.2CH.sub.3 CF.sub.3 [01542]
CH.sub.3 [01543]
4-24 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01544]
[01545]
4-25 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01546]
4-26 SO.sub.2CH.sub.3 CF.sub.3 [01547]
CH.sub.3 [01548]
4-27 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01549]
[01550]
4-28 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01551]
4-29 SO.sub.2CH.sub.3 CF.sub.3 [01552]
CH.sub.3 [01553]
4-30 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01554]
[01555]
4-31 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 [01556]
4-32 SO.sub.2CH.sub.3 CF.sub.3 [01557]
CH.sub.3 [01558]
4-33 SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 [01559]
[01560]
4-34 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01561]
4-35 NO.sub.2 SO.sub.2CH.sub.3 [01562]
CH.sub.3 [01563]
4-36 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 [01564]
[01565]
4-37 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01566]
4-38 NO.sub.2 SO.sub.2CH.sub.3 [01567]
CH.sub.3 [01568]
4-39 NO.sub.2 SO.sub.2CH.sub.3 CH.sub.3 [01569]
[01570]
4-40 NO.sub.2 Cl CH.sub.3 CH.sub.3 [01571]
4-41 NO.sub.2 Cl [01572]
CH.sub.3 [01573]
4-42 NO.sub.2 Cl CH.sub.3 [01574]
[01575]
4-43 Cl Cl CH.sub.3 CH.sub.3 [01576]
4-44 Cl Cl [01577]
CH.sub.3 [01578]
4-45 Cl Cl CH.sub.3 [01579]
[01580]
4-46 Cl Cl CH.sub.3 CH.sub.3 [01581]
4-47 Cl Cl [01582]
CH.sub.3 [01583]
4-48 Cl Cl CH.sub.3 [01584]
[01585]
4-49 Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01586]
4-50 Cl SO.sub.2CH.sub.3 [01587]
CH.sub.3 [01588]
4-51 Cl SO.sub.2CH.sub.3 CH.sub.3 [01589]
[01590]
4-52 Cl SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01591]
4-53 Cl SO.sub.2CH.sub.3 [01592]
CH.sub.3 [01593]
4-54 Cl SO.sub.2CH.sub.3 CH.sub.3 [01594]
[01595]
4-55 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01596]
4-56 CH.sub.3 SO.sub.2CH.sub.3 [01597]
CH.sub.3 [01598]
4-57 CH.sub.3 SO.sub.2CH.sub.3 CH.sub.3 [01599]
[01600]
4-58 CN SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01601]
4-59 CN SO.sub.2CH.sub.3 [01602]
CH.sub.3 [01603]
4-60 CN SO.sub.2CH.sub.3 CH.sub.3 [01604]
[01605]
4-61 CF.sub.3 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01606]
4-62 CF.sub.3 SO.sub.2CH.sub.3 [01607]
CH.sub.3 [01608]
4-63 CF.sub.3 SO.sub.2CH.sub.3 CH.sub.3 [01609]
[01610]
4-64 [01611]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01612]
4-65 [01613]
SO.sub.2CH.sub.3 [01614]
CH.sub.3 [01615]
4-66 [01616]
SO.sub.2CH.sub.3 CH.sub.3 [01617]
[01618]
4-67 [01619]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01620]
4-68 [01621]
SO.sub.2CH.sub.3 [01622]
CH.sub.3 [01623]
4-69 [01624]
SO.sub.2CH.sub.3 CH.sub.3 [01625]
[01626]
4-70 [01627]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01628]
4-71 [01629]
SO.sub.2CH.sub.3 [01630]
CH.sub.3 [01631]
4-72 [01632]
SO.sub.2CH.sub.3 CH.sub.3 [01633]
[01634]
4-73 [01635]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01636]
4-74 [01637]
SO.sub.2CH.sub.3 [01638]
CH.sub.3 [01639]
4-75 [01640]
SO.sub.2CH.sub.3 CH.sub.3 [01641]
[01642]
4-76 [01643]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01644]
4-77 [01645]
SO.sub.2CH.sub.3 [01646]
CH.sub.3 [01647]
4-78 [01648]
SO.sub.2CH.sub.3 CH.sub.3 [01649]
[01650]
4-79 [01651]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01652]
4-80 [01653]
SO.sub.2CH.sub.3 [01654]
CH.sub.3 [01655]
4-81 [01656]
SO.sub.2CH.sub.3 CH.sub.3 [01657]
[01658]
4-82 [01659]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01660]
4-83 [01661]
SO.sub.2CH.sub.3 [01662]
CH.sub.3 [01663]
4-84 [01664]
SO.sub.2CH.sub.3 CH.sub.3 [01665]
[01666]
4-85 SO.sub.2CH═CH.sub.2 SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01667]
4-86 SO.sub.2CH═CH.sub.2 SO.sub.2CH.sub.3 [01668]
CH.sub.3 [01669]
4-87 SO.sub.2CH═CH.sub.2 SO.sub.2CH.sub.3 CH.sub.3 [01670]
[01671]
4-88 [01672]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01673]
4-89 [01674]
SO.sub.2CH.sub.3 [01675]
CH.sub.3 [01676]
4-90 [01677]
SO.sub.2CH.sub.3 CH.sub.3 [01678]
[01679]
4-91 [01680]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01681]
4-92 [01682]
SO.sub.2CH.sub.3 [01683]
CH.sub.3 [01684]
4-93 [01685]
SO.sub.2CH.sub.3 CH.sub.3 [01686]
[01687]
4-94 [01688]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01689]
4-95 [01690]
SO.sub.2CH.sub.3 [01691]
CH.sub.3 [01692]
4-96 [01693]
SO.sub.2CH.sub.3 CH.sub.3 [01694]
[01695]
4-97 [01696]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01697]
4-98 [01698]
SO.sub.2CH.sub.3 [01699]
CH.sub.3 [01700]
4-99 [01701]
SO.sub.2CH.sub.3 CH.sub.3 [01702]
[01703]
4-100 [01704]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01705]
4-101 [01706]
SO.sub.2CH.sub.3 [01707]
CH.sub.3 [01708]
4-102 [01709]
SO.sub.2CH.sub.3 CH.sub.3 [01710]
[01711]
4-103 [01712]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01713]
4-104 [01714]
SO.sub.2CH.sub.3 [01715]
CH.sub.3 [01716]
4-105 [01717]
SO.sub.2CH.sub.3 CH.sub.3 [01718]
[01719]
4-106 [01720]
SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 [01721]
4-107 [01722]
SO.sub.2CH.sub.3 [01723]
CH.sub.3 [01724]
4-108 [01725]
SO.sub.2CH.sub.3 CH.sub.3 [01726]
[01727]
4-109 [01728]
CF.sub.3 CH.sub.3 CH.sub.3 [01729]
4-110 [01730]
CF.sub.3 CH.sub.3 CH.sub.3 [01731]
4-111 [01732]
CF.sub.3 CH.sub.3 CH.sub.3 [01733]
4-112 [01734]
CF.sub.3 CH.sub.3 CH.sub.3 [01735]
4-113 [01736]
CF.sub.3 CH.sub.3 CH.sub.3 [01737]
4-114 [01738]
CF.sub.3 CH.sub.3 CH.sub.3 [01739]
4-115 [01740]
CF.sub.3 CH.sub.3 CH.sub.3 [01741]
4-116 [01742]
CF.sub.3 CH.sub.3 CH.sub.3 [01743]
4-117 [01744]
CF.sub.3 CH.sub.3 CH.sub.3 [01745]
4-118 [01746]
CF.sub.3 CH.sub.3 CH.sub.3 [01747]
4-119 [01748]
CF.sub.3 CH.sub.3 CH.sub.3 [01749]
4-120 [01750]
CF.sub.3 CH.sub.3 CH.sub.3 [01751]
4-121 [01752]
CF.sub.3 CH.sub.3 CH.sub.3 [01753]
4-122 [01754]
CF.sub.3 CH.sub.3 CH.sub.3 [01755]
4-123 [01756]
CF.sub.3 CH.sub.3 CH.sub.3 [01757]
4-124 [01758]
CF.sub.3 CH.sub.3 CH.sub.3 [01759]
4-125 [01760]
CF.sub.3 CH.sub.3 CH.sub.3 [01761]
4-126 [01762]
CF.sub.3 CH.sub.3 CH.sub.3 [01763]
4-127 [01764]
CF.sub.3 CH.sub.3 CH.sub.3 [01765]
4-128 [01766]
CF.sub.3 CH.sub.3 CH.sub.3 [01767]
4-129 [01768]
CF.sub.3 CH.sub.3 CH.sub.3 [01769]
4-130 [01770]
CF.sub.3 CH.sub.3 CH.sub.3 [01771]
4-131 [01772]
CF.sub.3 CH.sub.3 CH.sub.3 [01773]
4-132 [01774]
CF.sub.3 CH.sub.3 CH.sub.3 [01775]
4-133 [01776]
CF.sub.3 CH.sub.3 CH.sub.3 [01777]
4-134 [01778]
CF.sub.3 CH.sub.3 CH.sub.3 [01779]
4-135 [01780]
CF.sub.3 CH.sub.3 CH.sub.3 [01781]
4-136 [01782]
CF.sub.3 CH.sub.3 CH.sub.3 [01783]
4-137 [01784]
CF.sub.3 CH.sub.3 CH.sub.3 [01785]
4-138 [01786]
CF.sub.3 CH.sub.3 CH.sub.3 [01787]
4-139 [01788]
CF.sub.3 CH.sub.3 CH.sub.3 [01789]
4-140 H Cl CH.sub.3 CH.sub.3 [01790]
white solid (122-126) 4-141 H Cl CH.sub.3 CH.sub.3 [01791]
yellow solid (105-109) .sup.1H NMR data of part of compounds is as follows:
[0121] Compound 1-1 (600 MHz, DMSO-d.sub.6): 8.11 (s, 2H), 7.63-7.67 (m, 3H), 7.42-7.51 (m, 4H), 6.28 (d, 1H), 3.57 (s, 3H), 3.34 (s, 3H), 2.33 (s, 3H).
[0122] Compound 1-7 (600 MHz, CDCl.sub.3): 8.18 (s, 1H), 7.81 (d, 1H), 7.45 (d, 1H), 7.37 (d, 1H), 6.96 (dd, 1H), 6.90 (s, 1H), 6.82 (d, 1H), 6.03 (s, 2H), 5.76 (d, 1H), 3.57 (s, 3H), 3.26 (s, 3H), 2.42 (s, 3H).
[0123] Compound 1-16 (600 MHz, CDCl.sub.3): 8.03 (d, 1H), 7.59 (d, 1H), 7.37-7.48 (m, 6H), 6.09 (d, 1H), 4.98 (s, 2H), 3.61 (s, 3H), 3.47 (s, 3H), 2.81 (s, 3H), 2.47 (s, 3H).
[0124] Compound 1-18 (600 MHz, DMSO-d.sub.6): 7.98 (d, 1H), 7.56-7.65 (m, 4H), 6.98 (d, 2H), 6.15 (d, 1H), 4.86 (s, 2H), 3.82 (s, 3H), 3.57 (s, 3H), 3.34 (s, 3H), 2.94 (s, 3H), 2.35 (s, 3H).
[0125] Compound 1-20 (600 MHz, DMSO-d.sub.6): 7.98 (d, 1H), 7.90 (d, 2H), 7.78 (d, 2H), 7.70 (d, 1H), 7.60 (d, 1H), 6.50 (d, 1H), 4.84 (s, 2H), 3.60 (s, 3H), 3.32 (s, 3H), 3.01 (s, 3H), 2.34 (s, 3H).
[0126] Compound 1-21 (600 MHz, DMSO-d.sub.6): 8.00 (d, 1H), 7.74-7.79 (m, 6H), 7.68 (d, 1H), 7.61 (d, 1H), 7.50 (t, 2H), 7.42 (t, 1H), 6.38 (d, 1H), 4.86 (s, 2H), 3.60 (s, 3H), 3.34 (s, 3H), 2.97 (s, 3H), 2.34 (s, 3H).
[0127] Compound 1-22 (600 MHz, DMSO-d.sub.6): 7.98 (d, 1H), 7.58 (d, 1H), 7.52 (d, 1H), 7.33 (s, 1H), 7.19 (d, 1H), 6.97 (d, 1H), 6.18 (d, 1H), 6.11 (s, 2H), 4.86 (s, 2H), 3.57 (s, 3H), 3.35 (s, 3H), 2.99 (s, 3H), 2.34 (s, 3H).
[0128] Compound 1-31 (600 MHz, CDCl.sub.3): 8.01 (d, 1H), 7.63 (d, 1H), 7.44-7.49 (m, 5H), 7.28 (d, 1H), 6.03 (d, 1H), 3.62 (s, 3H), 2.84 (s, 3H), 2.67 (s, 3H), 2.45 (s, 3H).
[0129] Compound 1-37 (600 MHz, DMSO-d.sub.6): 7.92 (d, 1H), 7.55 (d, 1H), 7.42 (d, 11H), 7.37 (s, 1H), 7.22 (d, 1H), 6.98 (d, 1H), 6.21 (d, 1H), 6.11 (s, 2H), 3.56 (s, 3H), 2.99 (s, 3H), 2.59 (s, 3H), 2.33 (s, 3H).
[0130] Compound 1-42 (600 MHz, CDCl.sub.3): 8.05 (d, 1H), 7.71 (t, 2H), 7.35 (d, 1H), 7.06 (s, 1H), 7.05 (s, 1H), 6.86 (d, 1H), 6.18 (d, 1H), 6.06 (s, 2H), 3.74 (s, 3H), 3.03 (s, 3H), 2.76 (s, 3H).
[0131] Compound 1-76 (600 MHz, DMSO-d.sub.6): 7.99 (d, 1H), 7.60-7.70 (m, 4H), 7.43-7.51 (m, 3H), 6.34 (d, 1H), 4.95 (s, 2H), 3.65 (t, 2H), 3.60 (s, 3H), 3.47 (t, 2H), 3.23 (s, 3H), 2.99 (s, 3H), 2.34 (s, 3H).
[0132] Compound 1-81 (600 MHz, CDCl.sub.3): 8.07 (d, 1H), 7.65-7.67 (m, 3H), 7.62 (d, 2H), 7.58 (d, 2H), 7.46-7.48 (m, 2H), 7.39-7.41 (m, 2H), 6.10 (d, J=15.6 Hz, 1H), 5.10 (s, 2H), 3.76-3.78 (m, 2H), 3.62 (s, 3H), 3.58-3.59 (m, 2H), 3.34 (s, 3H), 2.99 (s, 3H), 2.46 (s, 3H).
[0133] Compound 1-82 (600 MHz, CDCl.sub.3): 8.04 (d, 1H), 7.48 (d, 1H), 7.37 (d, 1H), 6.99-7.00 (m, 2H), 6.83 (d, 1H), 6.04 (s, 2H), 5.86 (d, 1H), 5.10 (s, 2H), 3.76-3.78 (m, 2H), 3.60 (s, 3H), 3.58-3.59 (m, 2H), 3.35 (s, 3H), 3.03 (s, 3H), 2.46 (s, 3H).
[0134] Compound 1-115 (600 MHz, CDCl.sub.3): 7.85 (d, 1H), 7.62 (d, 1H), 7.40-7.50 (m, 5H), 7.18 (d, 1H), 6.09 (d, 1H), 4.00 (s, 3H), 3.62 (s, 3H), 2.83 (s, 3H), 2.44 (s, 3H).
[0135] Compound 1-223 (600 MHz, DMSO-d.sub.6): 7.97 (d, 2H), 7.65-7.71 (m, 4H), 7.44-7.48 (m, 31H), 6.40 (d, 1H), 3.60 (s, 3H), 2.93 (s, 3H), 2.32 (s, 3H).
[0136] Compound 1-226 (600 MHz, DMSO-d.sub.6): 8.01 (s, 1H), 7.90 (d, 1H), 7.62 (d, 1H), 7.55 (d, 1H), 7.37 (s, 1H), 7.21 (d, 1H), 6.97 (d, 1H), 6.24 (d, 1H), 6.11 (s, 2H), 3.58 (s, 3H), 2.99 (s, 3H), 2.33 (s, 3H).
[0137] Compound 1-229 (600 MHz, DMSO-d.sub.6): 7.73 (d, 2H), 7.60 (d, 1H), 7.56 (d, 1H), 7.46-7.52 (m, 3H), 7.43 (dd, 1H), 7.36 (d, 1H), 6.39 (d, 1H), 3.59 (s, 3H), 2.33 (s, 3H).
[0138] Compound 1-232 (600 MHz, DMSO-d.sub.6): 7.59 (s, 1H), 7.46 (d, 1H), 7.40-7.43 (m, 2H), 7.34 (d, 1H), 7.22 (d, 1H), 7.00 (d, 1H), 6.23 (d, 1H), 6.12 (s, 2H), 3.57 (s, 3H), 2.32 (s, 3H).
[0139] Compound 1-235 (600 MHz, DMSO-d.sub.6): 8.58 (s, 1H), 8.36 (d, 1H), 7.84 (d, 1H), 7.69 (d, 2H), 7.62 (d, 1H), 7.44-7.51 (m, 3H), 6.37 (d, 1H), 3.58 (s, 3H), 3.01 (s, 3H), 2.35 (s, 3H).
[0140] Compound 1-238 (600 MHz, DMSO-d.sub.6): 8.58 (s, 1H), 8.34 (d, 1H), 7.82 (d, 1H), 7.51 (d, 1H), 7.36 (s, 1H), 7.20 (d, 1H), 6.98 (d, 1H), 6.20 (d, 1H), 6.12 (s, 2H), 3.55 (s, 3H), 3.07 (s, 3H), 2.36 (s, 3H).
[0141] Compound 1-259 (600 MHz, DMSO-d.sub.6): 7.68-7.70 (m, 3H), 7.62 (d, 1H), 7.48 (t, 1H), 7.42-7.44 (m, 2H), 7.23 (d, 1H), 6.40 (d, 1H), 4.01 (t, 2H), 3.62 (t, 2H), 3.59 (s, 3H), 3.30 (s, 3H), 2.88 (s, 3H), 2.34 (s, 3H), 2.17 (s, 3H).
[0142] Compound 1-262 (600 MHz, CDCl.sub.3): 7.78 (d, 1H), 7.44 (d, 1H), 7.13 (d, 1H), 6.93-6.96 (m, 2H), 6.81 (d, 1H), 6.01 (s, 2H), 5.83 (d, 1H), 4.09 (t, 2H), 3.69 (t, 2H), 3.58 (s, 3H), 3.40 (s, 3H), 2.96 (s, 3H), 2.39 (s, 3H), 2.26 (s, 3H).
[0143] Compound 1-265 (600 MHz, CDCl.sub.3): 7.82 (d, 1H), 7.58 (d, 1H), 7.41-7.49 (m, 5H), 7.17 (d, 1H), 6.07 (d, 1H), 3.85 (s, 3H), 3.63 (s, 3H), 2.84 (s, 3H), 2.44 (s, 3H), 2.28 (s, 3H).
[0144] Compound 1-268 (600 MHz, CDCl.sub.3): 7.95 (d, 1H), 7.59 (d, 1H), 7.41-7.48 (m, 5H), 7.22 (d, 1H), 5.98 (d, 1H), 3.61 (s, 3H), 2.81 (s, 3H), 2.52 (s, 3H), 2.42 (s, 3H), 2.23 (s, 3H).
[0145] Compound 1-280 (600 MHz, CDCl.sub.3): 7.78 (d, 1H), 7.55 (d, 1H), 7.39-7.47 (m, 5H), 7.12 (d, 1H), 6.04 (d, 1H), 3.97 (q, 2H), 3.61 (s, 3H), 2.83 (s, 3H), 2.42 (s, 3H), 2.24 (s, 3H), 1.37 (t, 3H).
[0146] Compound 1-292 (600 MHz, CDCl.sub.3): 8.00 (d, 1H), 7.79 (d, 1H), 7.75 (s, 1H), 7.53-7.56 (m, 3H), 7.41-7.47 (m, 3H), 6.40 (d, 1H), 4.54 (t, 2H), 3.75 (s, 3H), 3.29 (brs, 2H), 2.92 (s, 3H), 2.28 (s, 3H).
[0147] Compound 1-346 (600 MHz, CDCl.sub.3): 7.85 (d, 1H), 7.57 (d, 1H), 7.43-7.50 (m, 5H), 7.27 (d, 1H), 6.05 (d, 1H), 4.34 (q, 2H), 3.63 (s, 3H), 2.80 (s, 3H), 2.47 (s, 3H), 2.31 (s, 3H).
[0148] Compound 1-349 (600 MHz, CDCl.sub.3): 7.83 (d, 1H), 7.58 (d, 1H), 7.41-7.49 (m, 5H), 7.17 (d, 1H), 6.05 (d, 1H), 4.27-4.31 (m, 1H), 3.81-3.39 (m, 4H), 3.63 (s, 3H), 2.91 (s, 3H), 2.44 (s, 3H), 2.30 (s, 3H), 1.94-1.99 (m, 1H), 1.84-1.91 (m, 2H), 1.49-1.55 (m, 1H).
[0149] Compound 1-367 (600 MHz, CDCl.sub.3): 8.04 (s, 1H), 7.46-7.60 (m, 7H), 7.33 (d, 1H), 6.06 (d, 1H), 3.58 (s, 3H), 2.47 (s, 3H).
[0150] Compound 1-370 (600 MHz, CDCl.sub.3): 7.82 (d, 1H), 7.52 (d, 1H), 7.43 (d, 2H), 7.17 (d, 1H), 6.92 (d, 2H), 5.88 (d, 1H), 4.10 (t, 2H), 3.86 (s, 3H), 3.69 (t, 2H), 3.61 (s, 3H), 3.42 (s, 3H), 2.91 (s, 3H), 2.44 (s, 3H), 2.29 (s, 3H).
[0151] Compound 1-371 (600 MHz, CDCl.sub.3): 7.93 (d, 1H), 7.50-7.56 (m, 4H), 7.42-7.49 (m, 3H), 7.29 (d, 1H), 6.10 (d, 1H), 3.61 (s, 3H), 3.26 (s, 3H), 2.40 (s, 3H).
[0152] Compound 1-372 (600 MHz, CDCl.sub.3): 7.86 (d, 1H), 7.81 (d, 1H), 7.70 (s, 1H), 7.55-7.57 (m, 2H), 7.41-7.46 (m, 3H), 7.26 (d, 1H), 6.44 (d, 1H), 4.17 (t, 2H), 4.03-4.07 (m, 2H), 3.75 (t, 2H), 3.44 (s, 3H), 3.10 (s, 3H), 2.33 (s, 3H), 1.46 (t, 3H).
[0153] Compound 1-373 (600 MHz, CDCl.sub.3): 7.87 (d, 1H), 7.65 (d, 1H), 7.41-7.51 (m, 5H), 7.19 (d, 1H), 6.11 (d, 1H), 4.32 (t, 2H), 3.79 (t, 2H), 3.62 (s, 3H), 3.57 (q, 2H), 2.89 (s, 3H), 2.43 (s, 3H), 1.22 (t, 3H).
[0154] Compound 1-374 (600 MHz, CDCl.sub.3): 7.87 (d, 1H), 7.64 (d, 1H), 7.41-7.51 (m, 5H), 7.18 (d, 1H), 6.10 (d, 1H), 4.24 (t, 2H), 3.62 (s, 3H), 3.55 (t, 2H), 3.34 (s, 3H), 2.87 (s, 3H), 2.44 (s, 3H), 2.09-2.10 (m, 2H).
[0155] Compound 1-375 (600 MHz, CDCl.sub.3): 7.84 (d, 1H), 7.59 (d, 1H), 7.39-7.49 (m, 5H), 7.15 (d, 1H), 6.07 (d, 1H), 4.15 (t, 2H), 3.60 (s, 3H), 3.41 (t, 2H), 3.32 (s, 3H), 2.82 (s, 3H), 2.43 (s, 3H), 1.88-1.89 (m, 2H), 1.69-1.70 (m, 2H).
[0156] Compound 1-376 (600 MHz, CDCl.sub.3): 7.85 (d, 1H), 7.62 (d, 1H), 7.40-7.50 (m, 5H), 7.15 (d, 1H), 6.08 (d, 1H), 4.10 (td, 2H), 3.61 (s, 3H), 2.84 (s, 3H), 2.44 (s, 3H), 1.84 (p, 2H), 0.99 (t, 3H).
[0157] Compound 1-377 (600 MHz, CDCl.sub.3): 7.89 (d, 1H), 7.66 (d, 1H), 7.40-7.51 (m, 5H), 7.11 (d, 1H), 6.12 (d, 1H), 5.21-5.27 (m, 1H), 3.62 (s, 3H), 2.83 (s, 3H), 2.40 (s, 3H), 1.35 (d, 6H).
[0158] Compound 2-1 (600 MHz, CDCl.sub.3): 7.79 (d, 1H), 7.11 (d, 1H), 6.82-6.84 (m, 1H), 3.91 (s, 3H), 3.57 (s, 3H), 3.21 (s, 3H), 2.47 (s, 3H), 2.23 (s, 3H), 2.21 (q, 2H), 2.00-2.02 (m, 2H), 1.57-1.64 (m, 4H).
[0159] Compound 2-19 (600 MHz, CDCl.sub.3): 7.80 (d, 1H), 7.10 (d, 1H), 6.81-6.83 (m, 1H), 4.07 (q, 2H), 3.56 (s, 3H), 3.22 (s, 3H), 2.47 (s, 3H), 2.21 (s, 3H), 2.19-2.22 (m, 2H), 1.99-2.02 (m, 2H), 1.58-1.63 (m, 4H), 1.48 (t, 3H).
[0160] Compound 2-37 (600 MHz, CDCl.sub.3): 7.84 (d, 1H), 7.22 (d, 1H), 6.85-6.87 (m, 1H), 4.46 (q, 2H), 3.57 (s, 3H), 3.24 (s, 3H), 2.46 (s, 3H), 2.25 (s, 3H), 2.20 (q, 2H), 1.98-2.01 (m, 2H), 1.57-1.64 (m, 4H).
[0161] Compound 2-55 (600 MHz, CDCl.sub.3): 7.80 (d, 1H), 7.12 (d, 1H), 6.85 (t, 1H), 4.18 (t, 2H), 3.80 (t, 2H), 3.57 (s, 3H), 3.47 (s, 3H), 3.26 (s, 3H), 2.45 (s, 3H), 2.26 (s, 3H), 2.19-2.21 (m, 2H), 2.00-2.01 (m, 2H), 1.57-1.63 (m, 4H).
[0162] Compound 2-57 (600 MHz, CDCl.sub.3): 7.78 (d, 1H), 7.09 (d, 1H), 6.68 (t, 1H), 4.15 (t, 2H), 3.78 (t, 2H), 3.56 (s, 3H), 3.45 (s, 3H), 3.24 (s, 3H), 2.50-2.52 (m, 2H), 2.43 (s, 3H), 2.32-2.34 (m, 2H), 2.24 (s, 3H), 1.93-1.95 (m, 2H).
[0163] Compound 2-61 (600 MHz, CDCl.sub.3): 7.84 (d, 1H), 7.72 (s, 1H), 7.22 (d, 1H), 7.12-7.13 (m, 1H), 4.21 (t, 2H), 3.97-4.00 (m, 2H), 3.79 (t, 2H), 3.46 (s, 3H), 3.27 (s, 3H), 2.30 (s, 3H), 2.20-2.21 (m, 2H), 2.19-2.20 (m, 2H), 1.65-1.70 (m, 2H), 1.62-1.64 (m, 2H), 1.43 (t, 3H).
[0164] Compound 2-63 (600 MHz, CDCl.sub.3): 7.82-7.84 (m, 1H), 7.72 (s, 1H), 7.22 (d, 1H), 6.70 (d, 1H), 4.20 (d, 2H), 3.97-4.01 (m, 2H), 3.79 (d, 2H), 3.45 (s, 3H), 3.27 (s, 3H), 2.53-2.60 (m, 4H), 2.32 (s, 3H), 2.00-2.03 (m, 2H), 1.42 (t, 3H).
[0165] Compound 2-67 (600 MHz, CDCl.sub.3): 7.85 (d, 1H), 7.73 (s, 1H), 7.22 (d, 1H), 7.12-7.13 (m, 1H), 4.20 (t, 2H), 3.80 (t, 2H), 3.70 (s, 3H), 3.47 (s, 3H), 3.28 (s, 3H), 2.31 (s, 3H), 2.25-2.28 (m, 2H), 2.20-2.22 (m, 2H), 1.67-1.70 (m, 2H), 1.62-1.65 (m, 2H).
[0166] Compound 2-73 (600 MHz, CDCb3): 7.81 (d, 1H), 7.11 (d, 1H), 6.82-6.84 (m, 1H), 4.35-4.39 (m, 1H), 4.01 (d, 2H), 3.85-3.97 (m, 2H), 3.56 (s, 3H), 3.26 (s, 3H), 2.45 (s, 3H), 2.26 (s, 3H), 2.19-2.20 (m, 2H), 1.95-2.00 (m, 4H), 1.57-1.63 (m, 6H).
[0167] Compound 2-121 (600 MHz, CDCl.sub.3): 8.01 (d, 1H), 7.75 (s, 1H), 7.50 (d, 1H), 7.10-7.12 (m, 1H), 4.57 (t, 2H), 3.69 (s, 3H), 3.36-3.32 (m, 2H), 3.18 (s, 3H), 2.25-2.28 (m, 5H), 2.09-2.10 (m, 2H), 1.67-1.69 (m, 2H), 1.62-1.63 (m, 2H).
[0168] Compound 2-123 (600 MHz, CDCl.sub.3): 8.01 (d, 1H), 7.76 (s, 1H), 7.51 (d, 1H), 6.95-6.98 (m, 1H), 4.58 (t, 2H), 3.71 (s, 3H), 3.32-3.37 (m, 2H), 3.19 (s, 3H), 2.58-2.62 (m, 2H), 2.52-2.54 (m, 2H), 2.26 (s, 3H), 2.01-2.04 (m, 2H).
[0169] Compound 2-127 (600 MHz, CDCl.sub.3): 7.92 (d, 1H), 7.15 (d, 1H), 6.68-6.69 (m, 1H), 3.55 (s, 3H), 3.05 (s, 3H), 2.61 (s, 3H), 2.49 (s, 3H), 2.19 (s, 3H), 2.16-2.17 (m, 2H), 1.94-1.95 (m, 2H), 1.55-1.65 (m, 4H).
[0170] Compound 2-145 (600 MHz, CDCl.sub.3): 7.95 (d, 1H), 7.26 (d, 1H), 6.69-6.70 (m, 1H), 4.87 (s, 2H), 3.54 (s, 3H), 3.47 (s, 3H), 3.15 (s, 3H), 2.47 (s, 3H), 2.31 (s, 3H), 2.15-2.16 (m, 2H), 1.94-1.95 (m, 2H), 1.56-1.60 (m, 4H).
[0171] Compound 2-289 (600 MHz, CDCl.sub.3): 7.98 (d, 1H), 7.20 (d, 1H), 6.72 (s, 1H), 3.54 (s, 3H), 3.07 (s, 3H), 2.74 (s, 3H), 2.49 (s, 3H), 2.16-2.17 (m, 2H), 1.96-1.97 (m, 2H), 1.55-1.60 (m, 4H).
[0172] Compound 2-291 (600 MHz, CDCl.sub.3): 7.97 (d, 1H), 7.21 (d, 1H), 6.59 (s, 1H), 3.55 (s, 3H), 3.07 (s, 3H), 2.73 (s, 3H), 2.50-2.52 (m, 5H), 2.30-2.32 (m, 2H), 1.91-1.96 (m, 2H). Compound 2-307 (600 MHz, CDCl.sub.3): 8.01 (d, 1H), 7.31 (d, 1H), 6.71 (s, 1H), 5.01 (s, 2H), 3.52 (s, 3H), 3.46 (s, 3H), 3.19 (s, 3H), 2.46 (s, 3H), 2.13-2.14 (m, 2H), 1.94-1.95 (m, 2H), 1.54-1.56 (m, 4H).
[0173] Compound 2-309 (600 MHz, CDCl.sub.3): 8.03 (d, 1H), 7.33 (d, 1H), 6.60 (s, 1H), 5.03 (s, 2H), 3.56 (s, 3H), 3.48 (s, 3H), 3.22 (s, 3H), 2.49-2.52 (m, 5H), 2.30-2.33 (m, 2H), 1.91-1.96 (m, 2H).
[0174] Compound 2-343 (600 MHz, CDCl.sub.3): 8.01 (d, 1H), 7.54 (q, 1H), 7.23 (d, 1H), 6.77-6.78 (m, 1H), 3.55 (s, 3H), 3.26 (s, 3H), 2.45 (s, 3H), 2.17 (q, 2H), 2.00-2.01 (m, 2H), 1.56-1.63 (m, 4H).
[0175] Compound 2-379 (600 MHz, DMSO-d.sub.6): 8.22 (s, 1H), 8.16 (d, 1H), 7.61 (d, 1H), 6.58 (s, 1H), 3.51 (s, 3H), 3.32 (s, 3H), 2.36 (s, 3H), 2.02-2.04 (m, 2H), 1.85-1.87 (m, 2H), 1.40-1.50 (m, 4H).
[0176] Compound 2-380 (600 MHz, DMSO-d.sub.6): 8.21 (s, 1H), 8.17 (d, 1H), 7.61 (d, 1H), 6.49 (s, 1H), 3.52 (s, 3H), 3.32 (s, 3H), 2.34-2.36 (m, 5H), 2.20-2.21 (m, 2H), 1.76-1.82 (m, 2H).
[0177] Compound 2-381 (600 MHz, CDCl.sub.3): 8.05 (d, 1H), 7.34 (d, 1H), 6.74 (s, 1H), 5.16 (s, 2H), 3.77 (t, 2H), 3.56 (t, 2H), 3.55 (s, 3H), 3.34 (s, 3H), 3.29 (s, 3H), 2.50 (s, 3H), 2.16-2.17 (m, 2H), 1.98-1.99 (m, 2H), 1.57-1.61 (m, 4H).
[0178] Compound 2-382 (600 MHz, CDCl.sub.3): 8.04 (d, 1H), 7.34 (d, 1H), 6.61 (s, 1H), 5.15 (s, 2H), 3.77 (t, 2H), 3.56-3.58 (m, 5H), 3.34 (s, 3H), 3.29 (s, 3H), 2.50-2.53 (m, 5H), 2.31-2.33 (m, 2H), 1.92-1.97 (m, 2H).
[0179] Compound 2-383 (600 MHz, CDCh3): 7.91 (s, 1H), 7.79 (d, 1H), 7.37 (d, 1H), 6.77 (s, 1H), 3.54 (s, 3H), 3.03 (s, 3H), 2.47 (s, 3H), 2.15-2.16 (m, 2H), 1.97-1.98 (m, 2H), 1.55-1.58 (m, 4H).
[0180] Compound 2-384 (600 MHz, CDCl.sub.3): 7.93 (s, 1H), 7.81 (d, 1H), 7.40 (d, 1H), 6.67 (s, 1H), 3.58 (s, 3H), 3.07 (s, 3H), 2.49-2.52 (m, 5H), 2.33-2.34 (m, 2H), 1.93-1.96 (m, 2H).
[0181] Compound 2-385 (600 MHz, CDCl.sub.3): 7.36 (s, 1H), 7.22 (d, 1H), 7.15 (d, 1H), 6.87 (s, 1H), 3.57 (s, 3H), 2.47 (s, 3H), 2.20-2.22 (m, 2H), 2.04-2.06 (m, 2H), 1.61-1.63 (m, 4H).
[0182] Compound 2-386 (600 MHz, CDCl.sub.3): 7.36 (d, 1H), 7.24 (dd, 1H), 7.15 (d, 1H), 6.73 (s, 1H), 3.59 (s, 3H), 2.52-2.54 (m, 2H), 2.46 (s, 3H), 2.38-2.42 (m, 2H), 1.94-1.99 (m, 2H).
[0183] Compound 2-387 (600 MHz, CDCl.sub.3): 8.66 (s, 1H), 8.19 (d, 1H), 7.55 (d, 1H), 6.75 (s, 1H), 3.52 (s, 3H), 3.11 (s, 3H), 2.52 (s, 3H), 2.18-2.21 (m, 2H), 1.92-1.93 (m, 2H), 1.57-1.64 (m, 4H).
[0184] Compound 2-388 (600 MHz, CDCl.sub.3): 8.64 (s, 1H), 7.19 (d, 1H), 7.54 (d, 1H), 6.63 (s, 1H), 3.52 (s, 3H), 3.11 (s, 3H), 2.51-2.54 (m, 5H), 2.26-2.28 (m, 2H), 1.92-1.94 (m, 2H).
[0185] Compound 2-389 (600 MHz, CDCl.sub.3): 8.21 (d, 1H), 8.10 (dd, 1H), 7.37 (d, 1H), 6.82 (t, 1H), 3.56 (s, 3H), 2.47 (s, 3H), 2.06-2.08 (m, 2H), 1.98-1.99 (m, 2H), 1.44-1.53 (m, 4H).
[0186] Compound 2-390 (600 MHz, CDCl.sub.3): 8.20 (d, 1H), 8.09 (dd, 1H), 7.38 (d, 1H), 6.69 (s, 1H), 3.57 (s, 3H), 2.44 (s, 3H), 2.38-2.41 (m, 2H), 2.34-2.36 (m, 2H), 1.82-1.88 (m, 2H).
[0187] Compound 2-391 (600 MHz, CDCl.sub.3): 8.09 (s, 1H), 7.63 (d, 1H), 7.28 (d, 1H), 6.83 (s, 1H), 3.52 (s, 3H), 2.51 (s, 3H), 2.20-2.21 (m, 2H), 1.98-1.99 (m, 2H), 1.62-1.64 (m, 4H).
[0188] Compound 2-392 (600 MHz, CDCl.sub.3): 8.08 (s, 1H), 7.63 (d, 1H), 7.29 (d, 1H), 6.71 (s, 1H), 3.54 (s, 3H), 2.53-2.55 (m, 2H), 2.50 (s, 3H), 2.34-2.36 (m, 2H), 1.96-1.99 (m, 2H).
[0189] Compound 2-414 (600 MHz, CDCl.sub.3): 7.83 (d, 1H), 7.07 (d, 1H), 6.90-6.91 (m, 1H), 4.77-4.81 (m, 1H), 3.57 (s, 3H), 3.19 (s, 3H), 2.36 (s, 3H), 2.23 (s, 3H), 2.17-2.20 (m, 2H), 2.05-2.07 (m, 2H), 1.57-1.63 (m, 4H), 1.34 (d, 6H).
[0190] Compound 2-415 (600 MHz, CDCl.sub.3): 7.83 (d, 1H), 7.08 (d, 1H), 6.76-6.77 (m, 1H), 4.76-4.81 (m, 1H), 3.59 (s, 3H), 3.20 (s, 3H), 2.50-2.54 (m, 2H), 2.40-2.43 (m, 2H), 2.37 (s, 3H), 2.24 (s, 3H), 1.93-1.98 (m, 2H), 1.35 (d, 6H).
[0191] Compound 2-416 (600 MHz, CDCl.sub.3): 7.79 (d, 1H), 7.11 (d, 1H), 6.76-6.78 (m, 1H), 4.16 (t, 2H), 3.79 (t, 2H), 3.55-3.59 (m, 4H), 3.47 (s, 3H), 3.24 (s, 3H), 2.24 (s, 3H), 2.17-2.19 (m, 2H), 1.96-1.97 (m, 2H), 1.59-1.63 (m, 4H), 1.32 (d, 6H).
[0192] Compound 2-417 (600 MHz, CDCl.sub.3): 7.79 (d, 1H), 7.11 (d, 1H), 6.79-6.81 (m, 1H), 4.17 (t, 2H), 3.79 (t, 2H), 3.56 (s, 3H), 3.47 (s, 3H), 3.25 (s, 3H), 2.91 (q, 2H), 2.25 (s, 3H), 2.18-2.20 (m, 2H), 1.97-1.99 (m, 2H), 1.59-1.64 (m, 4H), 1.28 (t, 3H).
[0193] Compound 2-418 (600 MHz, CDCl.sub.3): 7.81 (d, 1H), 7.16 (d, 1H), 7.09 (t, 1H), 6.86-6.87 (m, 1H), 4.17 (t, 2H), 3.79 (t, 2H), 3.69 (s, 3H), 3.47 (s, 3H), 3.26 (s, 3H), 2.27 (s, 3H), 2.18-2.20 (m, 2H), 1.98-2.00 (m, 2H), 1.59-1.63 (m, 4H).
[0194] Compound 2-419 (600 MHz, CDCl.sub.3): 7.80 (d, 1H), 7.15 (d, 1H), 6.86-6.87 (m, 1H), 4.17 (t, 2H), 3.79 (t, 2H), 3.52 (s, 3H), 3.47 (s, 3H), 3.25 (s, 3H), 2.34-2.39 (m, 1H), 2.28 (s, 3H), 2.18-2.21 (m, 2H), 2.02-2.04 (m, 2H), 1.58-1.64 (m, 4H), 0.89-0.98 (m, 4H).
[0195] Compound 2-420 (600 MHz, CDCl.sub.3): 7.80 (d, 1H), 7.12 (d, 1H), 6.85-6.87 (m, 1H), 4.17 (t, 2H), 3.85 (q, 2H), 3.79 (t, 2H), 3.47 (s, 3H), 3.25 (s, 3H), 2.44 (s, 3H), 2.26 (s, 3H), 2.19-2.21 (m, 2H), 2.02-2.04 (m, 2H), 1.57-1.62 (m, 4H), 1.38 (t, 3H).
[0196] Compound 2-421 (600 MHz, CDCl.sub.3): 8.02 (d, 1H), 7.31 (d, 1H), 6.72-6.73 (m, 1H), 5.14 (s, 2H), 4.04-4.05 (m, 1H), 3.79-3.80 (m, 1H), 3.72-3.73 (m, 1H), 3.62-3.65 (m, 2H), 3.53 (s, 3H), 3.27 (s, 3H), 2.48 (s, 3H), 2.15-2.17 (m, 2H), 1.97-2.00 (m, 2H), 1.91-1.92 (m, 1H), 1.84-1.87 (m, 2H), 1.57-1.60 (m, 5H).
[0197] Compound 3-109 (600 MHz, CDCl.sub.3): 8.64 (d, 1H), 7.88-7.92 (m, 1H), 7.63 (d, 1H), 7.51 (d, 2H), 7.39-7.47 (m, 3H), 7.33 (d, 1H), 6.22 (d, 1H), 3.67 (s, 3H), 2.40 (s, 3H).
[0198] Compound 4-140 (600 MHz, CDCl.sub.3): 8.54 (d, 1H), 7.81-7.85 (m, 1H), 7.35 (d, 1H), 6.91-6.97 (m, 1H), 3.62 (s, 3H), 2.42 (s, 3H), 2.18-2.24 (m, 2H), 2.01-2.06 (m, 2H), 1.55-1.64 (m, 4H).
[0199] Compound 4-141 (600 MHz, CDCl.sub.3): 8.56 (d, 1H), 7.83-7.87 (m, 1H), 7.35 (d, 1H), 6.80-6.85 (m, 1H), 3.62 (s, 3H), 2.50-2.55 (m, 2H), 2.38-2.43 (m, 5H), 1.89-2.00 (m, 2H).
Biometric Test Examples
Embodiment 4 Determination of Herbicidal Activity
[0200] Seeds of broadleaf weeds (zinnia and piemarker) or grassy weeds (green bristlegrass and barnyard grass) were respectively sown in a paper cup having a diameter of 7 cm and containing nutrient soil; after sowing, the seeds were covered with 1 cm of soil, the soil was pressed and watered, and then the seeds were cultivated in a greenhouse according to a conventional method; and stems and leaves were sprayed after 2-3 leaf stage of the weeds.
[0201] After the original medicinal acetone was dissolved, the test requires to use 1‰ of Tween 80 to stand in running water to prepare the solution to be tested with a required concentration. According to the design dose of the test, spray treatment was carried out on a track-type crop sprayer (designed and produced by British Engineer Research Ltd.) (spray pressure is 1.95 kg/cm.sup.2, spray volume is 500 L/hm.sup.2 and track speed is 1.48 km/h). The test was repeated for three times. The test material was treated and then placed in an operation hall. The medicinal liquid was naturally dried in the shade, and then was placed in a greenhouse and managed according to the conventional method. The response of the weeds to the drug was observed and recorded. After treatment, the control effects of the test drug on the weeds were visually inspected regularly, expressed by 0-100%. “0” represents no control effect and “100%4” represents complete killing.
[0202] The test results show that the compounds of the formula I generally have high control effects on various weeds. Part of the test compounds, such as compounds 1-1, 1-7, 1-18, 1-20, 1-42, 1-76, 1-81, 1-82, 1-226, 1-259, 1-262, 1-265, 1-280, 1-292, 1-346, 1-349, 1-367, 1-370, 1-371, 2-1, 2-19, 2-37, 2-55, 2-67, 2-73, 2-121, 2-123, 2-289, 2-291, 2-307, 2-309, 2-379, 2-380, 2-383, 2-386, 2-391, 2416, 2417, 2-418, 2-419 and 2420, have good control effects on zinnia, piemarker, green bristlegrass or barnyard grass at the application dose of 600 g a.i./hm.sup.2, and the control effects are greater than or equal to 90%.
[0203] According to the above test method, part of the compounds of the formula I and KC.sub.1 are selected for activity test of controlling the zinnia. The results are shown in Table 5.
TABLE-US-00005 TABLE 5 Zinnia Control Activity of Part of Compounds of Formula 1 and Reference Compound KC.sub.1 (after emergence, control effect %) dose g a.i./hm.sup.2 Compound 600 150 37.5 1-42 100 100 100 1-81 100 95 90 KC.sub.1 0 0 0
[0204] According to the above test method, part of the compounds of the formula and KC.sub.1 are selected for activity test of controlling the piemarker. The results are shown in Table 6.
TABLE-US-00006 TABLE 6 Piemarker Control Activity of Part of Compounds of Formula 1 and Reference Compound KC.sub.1 (after emergence, control effect %) dose g a.i./hm.sup.2 Compound 600 150 37.5 1-1 100 95 90 1-42 100 95 90 1-259 / 100 100 1 -292 95 90 90 KC.sub.1 100 70 20 “/” in the table indicates no test.
[0205] According to the above test method, part of the compounds of the formula I and KC.sub.1 or KC.sub.2 are selected for activity test of controlling the green bristlegrass. The results are shown in Table 7.
TABLE-US-00007 TABLE 7 Green Bristlegrass Control Activity of Part of Compounds of Formula 1 and Reference Compounds KC.sub.1 or KC.sub.2 (after emergence, control effect %) dose g a.i./hm.sup.2 Compound 600 150 37.5 1-259 / 100 100 1-280 100 90 80 1 -292 95 90 90 KC.sub.1 10 10 10 2-121 98 90 80 2-123 100 100 90 KC.sub.2 / 60 30 “/” in the table indicates no test.
[0206] According to the above test method, part of the compounds of the formula I and KC.sub.1 or KC.sub.2 are selected for activity test of controlling the barnyard grass. The results are shown in Table 8.
TABLE-US-00008 TABLE 8 Barnyard Grass Control Activity of Part of Compounds of Formula 1 and Reference Compounds KC.sub.1 or KC.sub.2 (after emergence, control effect %) dose g a.i./hm.sup.2 Compound 600 150 37.5 1-42 100 95 80 1-81 95 90 80 1-82 100 95 90 1-259 / 100 100 1-280 100 95 85 1-292 100 95 90 KC.sub.1 0 0 0 2.37 100 100 95 2-67 100 100 90 2-73 100 100 95 2-123 100 100 100 KC.sub.2 / 90 60 “/” in the table indicates no test.
[0207] To sum up, the alkene-containing carboxylic ester compound of the present invention has excellent herbicidal activity, also has high herbicidal activity at a lower dosage, and can be used for agriculturally controlling various weeds.