Sulfamidosulfonamide derivatives and herbicides

TECHNICAL FIELD
The present invention relates to novel sulfamidosulfonamide derivatives and agriculturally suitable salts thereof, and herbicides containing them as active ingredients.
BACKGROUND TECHNIQUE
It is indispensable to use herbicides to protect important crop plants such as rice, wheat, corn, soybean, cotton and sugar beet from weeds and thereby to increase the harvest. Especially in recent years, a selective herbicide is desired which is capable of selectively killing weeds without showing any phytotoxicity against crop plants when applied to the foliages of crop plants and weeds simultaneously in a field where such useful crop plants and weeds are coexistent. Further, with a view to avoiding environmental pollution and reducing the costs for transportation and application, researches and developments have been conducted for many years for compounds having high herbicidal effects at low doses. Some of the compounds having such properties are presently used as selective herbicides. However, there still exists a need for better compounds having such properties.
As the prior art showing a chemical structure similar to that of the compounds of the present invention, Japanese Unexamined Patent Publication No. 45473/1990 discloses substituted sulfonyldiamides, and Japanese Unexamined Patent Publication No. 122671/1988 discloses 1-carbamoyl-2-pyrazolines. However, sulfamidosulfonamide derivatives having a pyrazoline structure like the compounds of the present invention have not been known at all, and they are novel compounds.
DISCLOSURE OF THE INVENTION
The present inventors have conducted extensive researches over years to develop selective herbicides for important crop plants and have studied herbicidal properties of many compounds with an aim to find out compounds having higher herbicidal activities as well as selectivity. As a result, it has been found that sulfamidosulfonamide derivatives of the following formula (1) and agriculturally suitable salts thereof (hereinafter referred to as the compounds of the present invention) exhibit remarkably strong herbicidal activities against many weeds in soil treatment or in foliage treatment and at the same time have a high level of safety for important crop plants such as wheat, corn, cotton, soybean, sugar beet and rice. The present invention has been accomplished on the basis of this discovery. On the other hand, since the compounds of the present invention show high herbicidal activities at a very low dose as compared with conventional herbicides, they are also useful as herbicides for orchards or for non-agricultural fields.
Namely, the present invention provides a sulfamidosulfonamide derivative of the formula (1) and an agriculturally suitable salt thereof: ##STR4## wherein Q is ##STR5## wherein R.sup.11 is a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.3-7 cycloalkyl group, a C.sub.1-6 alkyl group substituted by a C.sub.3-7 cycloalkyl group, a C.sub.2-6 alkenyl group, a C.sub.1-6 alkynyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 mono- or poly-halogenoalkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylthio group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylsulfonyl group, a C.sub.1-6 mono- or poly-halogenoalkyl group, a C.sub.1-6 alkyl group substituted by a cyano group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylcarbonyl group, a phenyl group or a benzyl group (provided that such a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a trifluoromethyl group, a nitro group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group and a C.sub.1-6 alkoxycarbonyl group);
R.sup.12 is a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a phenyl group or a benzyl group (provided that such a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a trifluoromethyl group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group and a C.sub.1-6 alkoxycarbonyl group);
R.sup.13 is a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.1-6 alkynyl group, a phenyl group or a benzyl group (provided that such a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a trifluoromethyl group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkoxycarbonyl group and a nitro group);
or, R.sup.12 and R.sup.13 form, together with the nitrogen atom to which they are bonded, a saturated 5-7 membered heterocyclic group;
or, R.sup.12 and R.sup.13 form, together with the oxygen atom and the nitrogen atom to which they are bonded, a saturated 5-7 membered heterocyclic group;
R.sup.21 is a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 mono- or poly-halogenoalkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylthio group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylsulfonyl group, a C.sub.1-6 mono- or poly-halogenoalkyl group, a C.sub.1-6 alkyl group substituted by a cyano group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylcarbonyl group, a phenyl group or a benzyl group (provided that such a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a trifluoromethyl group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkoxycarbonyl group and a nitro group);
R.sup.22 is a hydrogen atom or a C.sub.1-6 alkyl group;
R.sup.23 is a hydrogen atom or a C.sub.1-6 alkyl group;
R.sup.24 is a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a halogen atom, a C.sub.1-6 mono- or poly-halogenoalkyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.2-6 alkenyloxy group, a C.sub.1-6 alkyl group substituted by a C.sub.2-6 alkynyloxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 mono- or poly-halogenoalkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylthio group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylsulfonyl group, a C.sub.1-6 alkyl group substituted by a cyano group, a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 alkylcarbonyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylcarbonyl group, a phenyl group or a benzyl group (provided that such a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a trifluoromethyl group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkoxycarbonyl group and a nitro group);
R.sup.25 is a hydrogen atom or a C.sub.1-6 alkyl group;
R.sup.26 is a hydrogen atom or a C.sub.1-6 alkyl group;
R.sup.27 is a hydrogen atom or a C.sub.1-6 alkyl group;
R.sup.28 is a hydrogen atom, a halogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.1-6 mono- or poly-halogenoalkyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.2-6 alkenyloxy group, a C.sub.1-6 alkyl group substituted by a C.sub.2-6 alkynyloxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylthio group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylsulfonyl group, a C.sub.1-6 alkyl group substituted by a cyano group, a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 alkylcarbonyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylcarbonyl group, a phenyl group or a benzyl group (provided that such a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a trifluoromethyl group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkoxycarbonyl group and a nitro group);
X is an oxygen atom or a sulfur atom;
G is ##STR6## wherein each of a, b, c and d, which are independent from one another, is a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.1-6 alkyl group mono- or poly-substituted by a halogen atom, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkoxy group, a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylthio group, a C.sub.1-6 alkyl group substituted by a C.sub.1-6 alkylsulfonyl group, a C.sub.1-6 alkylthio group, a C.sub.1-6 alkylcarbonyl group, a C.sub.3-7 cycloalkyl group, a C.sub.3-7 cycloalkenyl group, a cyano group, a nitro group, a phenyl group or a benzyl group (provided that such a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a trifluoromethyl group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkoxycarbonyl group and a nitro group , a 5- or 6-membered heterocyclic group (provided that such a heterocyclic group contains from 1 to 3 hetero atoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms in the ring, or contains a sulfonyl group, and such a heterocyclic group may be substituted by one or more substituents selected from the group consisting of a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, a halogen atom, a trifluoromethyl group, a nitro group and a C.sub.1-6 alkoxycarbonyl group), a naphthyl group, a benzene-condensed heterocyclic group (provided that such a benzene-condensed heterocyclic group contains 1 or 2 hetero atoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms, and such a benzene-condensed heterocyclic group may be substituted by one or more substituents selected from the group consisting of a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, a halogen atom, a trifluoromethyl group, a nitro group and a C.sub.1-6 alkoxycarbonyl group).
The present invention also provides a selective herbicide containing one or more compounds of the present invention as active ingredients.
Further, the present invention provides a herbicidal composition comprising a herbicidally effective amount of one or more compounds of the present invention and an agricultural adjuvant.
Now, the present invention will be described in detail with reference to the preferred embodiments.
The compounds of the formula (1) of the present invention can easily be prepared by any one of the following reaction schemes 1 to 5. ##STR7## In the above formulas, Q, G and X are as defined above.
Namely, the reaction of a sulfamidosulfonyliso(thio)cyanate derivative (2) with a pyrazoline derivative (3), is conducted by using the sulfamidosulfonyliso(thio)cyanate derivative (2) in an amount of from 0.5 to 3.0 mols per mol of the pyrazoline derivative (3). Preferably the amount is within a range of from 0.8 to 1.2 mols.
The reaction temperature can be selected optionally within a range of from -50.degree. C. to 200.degree. C. However, the temperature is preferably within a range of from -20.degree. C. to 50.degree. C.
This reaction usually proceeds readily to present the compound (1) of the present invention. If the reaction tends to hardly proceed, a suitable base, for example, an organic base such as triethylamine, triethylenediamine, pyridine or 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), a metal alkoxide such as sodium methoxide or sodium ethoxide, a metal hydride such as sodium hydride, an alkyl metal such as n-butyl lithium, or an inorganic base such as potassium carbonate, potassium hydroxide or sodium hydroxide, may be added to facilitate the reaction. As the base, it is particularly preferred to employ an organic base or an inorganic base.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture.
After completion of the reaction, usual posttreatment is conducted to obtain the compound (1) of the present invention. The structure of the compound of the present invention was determined by e.g. IR, NMR or MASS. ##STR8## In the above formulas, Q, G and X are as defined above, and Y is a C.sub.1-6 alkyl group, a phenyl group or a benzyl group (provided that such an alkyl group, a phenyl group or a benzyl group may be substituted by one or more substituents selected from the group consisting of a C.sub.1-6 alkyl group, C.sub.1-6 alkoxy group and a halogen atom).
Namely, the reaction of a sulfamidosulfonamide derivative (4) with chloro(thio)formic acid ester or thio)carbonic acid diester is conducted by using the chloro(thio)formic acid ester or the (thio)carbonic acid diester in an amount of from 0.5 to 3.0 mols per mol of the sulfamidosulfonamide derivative (4). The amount is preferably within a range of from 0.8 to 1.2 mols.
The reaction temperature can be selected optionally within a range of from -50.degree. C. to 200.degree. C. However, it is preferably within a range of from -20.degree. C. to 100.degree. C.
This reaction is conducted by using various bases. The base is used in an amount of from 0.5 to 5.0 mols per mol of the sulfamidosulfonamide derivative (4). As a suitable base, an organic base such as triethylamine, triethylenediamine, pyridine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), a metal alkoxide such as sodium methoxide or sodium ethoxide, a metal hydride such as sodium hydride, an alkyl metal such as n-butyl lithium, or an inorganic base such as potassium carbonate, potassium hydroxide or sodium hydroxide, may, for example, be used. It is particularly preferred to employ an organic base or an inorganic base.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture.
After completion of the reaction, usual posttreatment is conducted to obtain an N-sulfamidosulfonyl(thio)carbamate derivative (5).
Then, the reaction of the N-sulfamidosulfonyl(thio)carbamate derivative (5) with a pyrazoline derivative (3) is conducted by using the pyrazoline derivative (3) in an amount of from 0.5 to 10.0 mols per mol of the N-sulfamidosulfonyl(thio)carbamate derivative (5). The amount is preferably within a range of from 0.5 to 3.0 mols.
The reaction temperature can be selected optionally within a range of from 0.degree. C. to 250.degree. C. However, it is preferably within a range of from 50.degree. C. to 150.degree. C.
This reaction usually proceeds readily to present the compound (1) of the present invention. However, if the reaction tends to hardly proceed, a suitable base, for example, an organic base such as triethylamine, triethylenediamine, pyridine or 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), a metal alkoxide such as sodium methoxide or sodium ethoxide, a metal hydride such as sodium hydride, an alkyl metal such as n-butyl lithium, or an inorganic base such as potassium carbonate, potassium hydroxide or sodium hydroxide, may be added to facilitate the reaction. As the base, it is particularly preferred to employ an organic base or an inorganic base.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture.
After completion of the reaction, usual posttreatment is conducted to obtain the compound (1) of the present invention. The structure of the compound of the present invention was determined by e.g. IR, NMR or MASS. ##STR9## In the above formulas, Q, G and Y are as defined above.
Namely, the reaction of a sulfamide (7) with an N-chlorosulfonylcarbamate derivative (6) is conducted by using the N-chlorosulfonylcarbamate derivative (6) in an amount of from 0.5 to 3.0 mols per mol of the sulfamide (7) The amount is preferably within a range of from 0.9 to 1.2 mols.
The reaction temperature may be selected optionally within a range of from -50.degree. C. to 100.degree. C. However, it is preferably within a range of from -20.degree. C. to 30.degree. C.
This reaction can be conducted by using various bases. The base is used in an amount of from 0.5 to 4.0 mols per mol of the sulfamide (7). As a suitable base, a metal hydride such as sodium hydride, a metal alkoxide such as sodium methoxide or sodium ethoxide, an alkyl metal such as n-butyl lithium, an organic base such as triethylamine, triethylenediamine, pyridine or 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), or an inorganic base such as potassium carbonate, potassium hydroxide or sodium hydroxide, may be employed. It is particularly preferred to employ a metal hydride, an organic base or an inorganic base.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture. It is particularly preferred to employ an ether or an amide.
After completion of the reaction, usual posttreatment is conducted to obtain an N-sulfamidosulfonylcarbamate derivative (5; X=0).
Then, the reaction of the N-sulfamidosulfonylcarbamate derivative (5; X=0) with a pyrazoline derivative (3) is conducted by using the pyrazoline derivative (3) in an amount of from 0.5 to 10.0 mols per mol of the N-sulfamidosulfonylcarbamate derivative (5; X=0). The amount is preferably within a range of from 0.5 to 3.0 mols.
The reaction temperature can be selected optionally within a range of from 0.degree. C. to 250.degree. C. However, it is preferably within a range of from 50.degree. C. to 150.degree. C.
This reaction usually proceeds readily to present the compound (1) of the present invention. However, if the reaction tends to hardly proceed, a suitable base, for example, an organic base such as triethylamine, triethylenediamine, pyridine or 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), a metal alkoxide such as sodium methoxide or sodium ethoxide, metal hydride such as sodium hydride, an alkyl metal such as n-butyl lithium, or an inorganic base such as potassium carbonate, potassium hydroxide or sodium hydroxide, may be added to facilitate the reaction. As the base, it is particularly preferred to employ an organic base or an inorganic base.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture.
After completion of the reaction, usual posttreatment is conducted to obtain the compound (1; X=0) of the present invention. The structure of the compound of the present invention was determined by e.g. IR, NMR or MASS. ##STR10## In the above formulas, Q, G and Y are as defined above.
Namely, the reaction of a sulfamidosulfonamide derivative (4) with a pyrazolinylformic acid ester (8) is conducted by using the pyrazolinylformic acid ester (8) in an amount of from 0.5 to 3.0 mols per mol of the sulfamidosulfonamide derivative (4). The amount is preferably within a range of from 0.8 to 1.2 mols.
The reaction temperature can be selected optionally within a range of from -50.degree. C. to 100.degree. C.
This reaction can be conducted by using various bases. The base is used in an amount of from 0.5 to 4.0 mols per mol of the sulfamidosulfonamide derivative (4). As a suitable base, an organic base such as triethylamine, triethylenediamine, pyridine or 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), an inorganic base such as potassium carbonate, potassium hydroxide or sodium hydroxide, an alkyl metal such as n-butyl lithium or trimethyl aluminum, a metal hydride such as sodium hydride, or a metal alkoxide such as sodium methoxide or sodium ethoxide, may be employed. It is particularly preferred to employ an organic base, an inorganic base or an alkyl metal.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture.
After completion of the reaction, usual posttreatment is conducted to obtain the compound (1; X=0) of the present invention. The structure of the compound of the present invention was determined by e.g. IR, NMR or MASS. ##STR11## In the above formulas, Q and G are as defined above.
Namely, the reaction of a pyrazoline derivative (3) with a chlorosulfonyl isocyanate is conducted by using the chlorosulfonyl isocyanate in an amount of from 0.5 to 3.0 mols per mol of the pyrazoline derivative (3). The amount is preferably within a range of from 0.8 to 1.2 mols.
The reaction temperature can be selected optionally within a range of from -50.degree. C. to 100.degree. C. However, it is preferably within a range of from -30.degree. C. to 50.degree. C.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture.
This reaction usually proceeds readily without using a base.
Then, a suitable base is added to the reaction system of the pyrazoline derivative (3) and the chlorosulfonyl isocyanate, and a sulfamide derivative (7) is reacted to obtain a compound of the present invention (1; X=0). The base is used in an amount of from 0.5 to 4.0 mols, preferably from 0.8 to 2.2 mols, per mol of the pyrazoline derivative (3). Further, the sulfamide derivative (7) is used in an amount of from 0.5 to 2.0 mols, preferably from 0.8 to 1.2 mols, per mol of the pyrazoline derivative (3).
As a suitable base, an organic base such as triethylamine, triethylenediamine, pyridine or 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), an inorganic base such as potassium carbonate, potassium hydroxide or sodium hydroxide, an alkyl metal such as n-butyl lithium, a metal hydride such as sodium hydride, or a metal alkoxide such as sodium methoxide or sodium ethoxide, may be employed. It is particularly preferred to employ an organic base, an inorganic base or a metal hydride.
The reaction temperature can be selected optionally within a range of from -50.degree. C. to 150.degree. C. However, it is preferably within a range of from -30.degree. C. to 60.degree. C.
After completion of the reaction, usual posttreatment is conducted to obtain the compound (1; X=0) of the present invention. The structure of the compound of the present invention was determined by e.g. IR, NMR or MASS.
The sulfamidosulfonyliso(thio)cyanate derivative (2) to be used in the Reaction scheme 1, can be prepared from the sulfamide derivative (7) or the sulfamidosulfonamide derivative (4) in accordance with the method disclosed in e.g. Japanese Unexamined Patent Publications No. 45473/1990, No. 151577/1989, No. 31775/1984, No. 148879/1983, No. 13266/1980 and No. 81320/1974.
Further, the sulfamidosulfonamide derivative (4) can be prepared from the sulfamide derivative (7) in accordance with the following Reaction schemes 6 and 7. ##STR12## In the above formulas, Q is as defined above.
In the Reaction scheme 6, removal of the tert-butyl group is conducted by using trifluoroacetic acid.
The amount of trifluoroacetic acid can be selected optionally from an equimolar amount to excess amount. Further, trifluoroacetic acid may be used as a solvent without any problem.
The reaction temperature can be selected optionally within a range of from -50.degree. C. to 80.degree. C. It is preferably within a range of from -20.degree. C. to 30.degree. C.
In a case where a solvent is employed in this reaction, a solvent inert to the reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be used. These solvents may be used alone or in combination as a mixture. ##STR13## In the above formulas, Q is as defined above.
In the Reaction scheme 7, the reaction of t-butanol with chlorosulfonyl isocyanate can be conducted by a method per se known, such as the one disclosed in Japanese Unexamined Patent Publication No. 101323/1975.
The reaction of sulfamide (7) with tert-butyl sulfamoyl chloride is conducted by using tert-butyl sulfamoyl chloride in an amount of from 0.5 to 3.0 mols per mol of the sulfamide (7).
The reaction temperature can be selected optionally within a range of from -50.degree. C. to 100.degree. C. However, it is preferably within a range of from -20.degree. C. to 30.degree. C.
This reaction can be conducted by using various bases. The base is used in an amount of from 0.5 to 4.0 mols per mol of the sulfamide (7). The amount is preferably within a range of from 0.8 to 2.2 mols. As a suitable base, a metal hydride such as sodium hydride, a metal alkoxide such as sodium ethoxide, an alkyl metal such as n-butyl lithium, an organic base such as triethylamine, pyridine or 1,8-diazabicyclo[5.4.0]-7-undecene, or an inorganic base such as potassium hydroxide, sodium hydroxide or potassium carbonate, may be employed.
As a solvent suitable for this reaction, a solvent inert to this reaction, for example, an aromatic hydrocarbon such as benzene, toluene or xylene, a halogenated hydrocarbon such as dichloromethane, chloroform or carbon tetrachloride, an ether such as diethyl ether, isopropyl ether, dioxane or tetrahydrofuran, a nitrile such as acetonitrile or propionitrile, a hydrocarbon such as petroleum ether, petroleum benzin or n-hexane, a ketone such as acetone or methyl ethyl ketone, an ester such as ethyl acetate, or an amide such as dimethylformamide, dimethylacetamide or hexamethylphosphoric acid triamide, may be mentioned. These solvents may be used alone or in combination as a mixture. It is particularly preferred to employ an ether or an amide.
In the Reaction scheme 3, the N-chlorosulfonylcarbamate derivative (6) can be prepared by a method per se known in accordance with e.g. Chemishe Berichte, vol. 96, p. 56 (1963).
The sulfamide (7) to be used as the starting material for the above reactions, can readily be prepared in accordance with e.g. Synthetic organic Chemistry, Japan, vol. 27 (No. 10), p. 980 (1969); U.S. Pat. No. 2,624,729; Chemishe Berichte, vol. 111, p. 1915 (1978); Japanese Unexamined Patent Publications No. 208289/1983, No. 79894/1978; Indian Journal of Chemistry, Section B, vol. 21B, p. 941 (1982); Journal of the American Chemical Society, vol. 66, p. 1242 (1944); U.S. Pat. No. 2,826,594.
As typical examples, syntheses of 2,4-dimethyl-1,2,5-thiadiazolidine-1,1-dioxide, 2-methoxy-1,2,5-thiadiazolidine-1,1-dioxide, N,N-dimethyl-N'-ethylsulfamide, N,N-dimethyl-N'-methoxysulfamide and N-methyl-N-methoxy-N'-ethylsulfamide, will be described by Reaction schemes 8 to 12: ##STR14##
The pyrazoline derivative (3) to be used as a starting material in the above reactions can readily be prepared in accordance with e.g. Japanese Unexamined Patent Publication No. 122671/1988; U.S. Pat. No. 3,322,831; Journal of the American Chemical Society, vol. 80, p. 1926 (1958); Chemishe Berichte, vol. 35, p. 968 (1902); Shin Jikken Kagaku Koza, vol. 14, p. 1423. Typical Examples will be described by Reaction Schemes 13 to 21: ##STR15##
Now, preparation of the compounds of the present invention will be described in further detail with reference to Reference Examples and Examples. However, it should be understood that the present invention is by no means restricted by such specific Examples.

REFERENCE EXAMPLE 1
Preparation of phenyl N-[(N-dimethylsulfamoyl-N-methyl amino)sulfonyl]carbamate ##STR16##
4.0 g (100 mmol) of 60% sodium hydride was washed with n-hexane and suspended in 100 ml of dry tetrahydrofuran (THF). Then, 6.9 g (50 mmol) of N,N,N'-trimethylsulfamide dissolved in 20 ml of dry THF was added thereto under cooling with ice, and the mixture was gradually heated and stirred at room temperature for 3 hours.
Then, 50 ml of a dry THF solution containing 13.0 g (55 mmol) of phenyl N-chlorosulfonylcarbamate was dropwise added thereto under cooling with ice, and the mixture was gradually heated to room temperature and then stirred at room temperature for 3 hours.
The reaction mixture was poured into 1000 ml of ice water containing 1.05 g of 35% hydrochloric acid and extracted with diethyl ether. The diethyl ether layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 16.0 g of phenyl N-[(N-dimethylsulfamoyl-N-methylamino)sulfonyl]carbamate as slightly yellow oil.
REFERENCE EXAMPLE 2
Preparation of phenyl N-[(N-dimethylsulfamoyl-N-methoxyamino)sulfonyl]carbamate ##STR17##
2.69 g (61.5 mmol) of 55% sodium hydride was washed with n-hexane and then suspended in 100 ml of dry THF. Then, 4.62 g (30 mmol) of N,N-dimethyl-N'-methoxysulfamide dissolved in 20 ml of THF was dropwise added thereto under cooling with ice. The mixture is heated to room temperature and then stirred at room temperature for one hour. Then, this reaction mixture was again cooled with ice, and 7.07 g (30 mmol) of phenyl N-chlorosulfonylcarbamate dissolved in 30 ml of dry THF was dropwise added thereto. The mixture was heated to room temperature and then stirred at room temperature for 30 minutes. The reaction mixture was poured into 500 ml of ice water containing 6.4 g of 35% hydrochloric acid and extracted three times with 80 ml of diethyl ether. The extract solution was washed three times with 100 ml of water and once with 100 ml of a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 10.1 g of phenyl N-[(N-dimethylsulfamoyl-N-methoxyamino)sulfonyl]carbamate as slightly yellow oil.
REFERENCE EXAMPLE 3
Preparation of phenyl N-[(N-(N-methyl-N-methoxyaminosulfonyl)-N-methylamino)sulfonyl]carbamate ##STR18##
A mixture comprising 7 g (63 mmol) of methylsulfamic acid, 13.2 g (63 mmol) of phosphorus pentachloride and 100 ml of dry benzene, was refluxed for one hour. The reaction mixture was left to cool, and the solvent was distilled off under reduced pressure to obtain 7.63 g of methylsulfamoyl chloride.
5.75 g (58.9 mmol) of N,O-dimethylhydroxylamine hydrochloride was suspended in 300 ml of dichloromethane, and 11.9 g (118 mmol) of triethylamine was added thereto. Then, the mixture was cooled with ice, and a dichloromethane solution of 7.63 g of methylsulfamoyl chloride was dropwise added, and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure. To the residue, 200 ml of benzene was added, and insoluble substance was filtered off. Then, the solvent was distilled off again under reduced pressure. By the distillation under reduced pressure, 4.4 g of N,N'-dimethyl-N'-methoxysulfamide was obtained (boiling point: 85.degree.-88.degree. C./1.9 mmHg).
1.15 g (28.8 mmol) of 60% sodium hydride was washed with n-hexane, and dry THF was added, and the mixture was cooled with ice. To this mixture, a THF solution containing 2 g (13 mmol) of N,N'-dimethyl-N'-methoxysulfamide was dropwise added. After stirring the mixture for 10 minutes, a dry THF solution containing 3.21 g (13.6 mmol) of phenyl N-chlorosulfonylcarbamate was dropwise added thereto. The mixture was stirred at room temperature for 7 hours. The reaction mixture was poured into 500 ml of ice water containing 3.5 g of 35% hydrochloric acid and extracted three times with diethyl ether. The diethyl ether layer was washed sequentially with water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 4.3 g of phenyl N-[(N-(N-methyl N-methoxyaminosulfonyl)-N-methylamino)sulfonyl]carbamate as slightly yellow oil.
REFERENCE EXAMPLE 4
Preparation of phenyl N-(2-methyl-tetrahydro-1,2,6-thiadiazine-1,1-dioxide-6-sulfonyl)carbamate ##STR19##
A mixture comprising 30 g (312 mmol) of sulfamide, 27.5 g (312 mmol) of N-methyl-1,3-propanediamine and 300 ml of dry pyridine was refluxed overnight at 130.degree. C. The mixture was left to cool, and then pyridine was distilled off under reduced pressure. To the residue, 200 ml of chloroform was added and insoluble substance was filtered off. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (CHCl.sub.3) and then subjected to distillation under reduced pressure to obtain 36.2 g of 2-methyl-tetrahydro-1,2,6-thiadiazine-1,1-dioxide (boiling point: 130.degree.-133.degree. C./0.23 mmHg).
Then, 5.87 g (147 mmol) of 60% sodium hydride was washed twice with 30 ml of n-hexane, and then 30 ml of dry THF was added thereto, and the mixture was cooled with ice. To this mixture, a dry THF solution containing 10.0 g (66.7 mmol) of 2-methyl-tetrahydro-1,2,6-thiadiazine-1,1-dioxide was dropwise added, and the mixture was stirred at room temperature for 2.5 hours. The solution was cooled again with ice, and a dry THF solution containing 16.5 g (70 mmol) of phenyl N-chlorosulfonylcarbamate, was dropwise added thereto. The mixture was stirred at room temperature for 2 hours, and then poured into 1500 ml of ice water containing 17.4 g of 35% hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layer was washed twice with water and once with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 20.0 g of the desired phenyl N-(2-methyltetrahydro-1,2,6-thiadiazine-1,1-dioxide-6-sulfonyl)carbamate. Melting point: 144.degree.-145.degree. C.
The structures and physical properties or characteristics of the compounds prepared in the same manner as in the above Reference Examples 1 to 4 are shown below:
______________________________________ ##STR20## Slightly yellow oil ##STR21## Slightly yellow oil ##STR22## Slightly yellow oil ##STR23## Slightly yellow oil ##STR24## m.p. 96-97.degree. C. ##STR25## Slightly yellow oil ##STR26## Slightly yellow oil ##STR27## Slightly yellow oil ##STR28## Slightly yellow oil ##STR29## Slightly yellow oil ##STR30## Slightly yellow oil ##STR31## Slightly yellow oil ##STR32## Slightly yellow oil ##STR33## Slightly yellow oil ##STR34## Slightly yellow oil ##STR35## Slightly yellow oil ##STR36## Slightly yellow oil ##STR37## Slightly yellow oil ##STR38## Slightly yellow oil ##STR39## Slightly yellow oil ##STR40## Slightly yellow oil ##STR41## Slightly yellow oil ##STR42## Slightly yellow oil ##STR43## Slightly yellow oil ##STR44## Slightly yellow oil ##STR45## Slightly yellow oil ##STR46## Slightly yellow oil ##STR47## m.p. 137.about. 139.degree. C. ##STR48## Slightly yellow oil ##STR49## Slightly yellow oil ##STR50## Slightly yellow oil ##STR51## Slightly yellow oil ##STR52## Slightly yellow oil ##STR53## Slightly yellow oil ##STR54## Slightly yellow oil ##STR55## Slightly yellow oil ##STR56## Slightly yellow oil ##STR57## Slightly yellow oil ##STR58## Slightly yellow oil ##STR59## Slightly yellow oil ##STR60## Slightly yellow oil ##STR61## Slightly yellow oil ##STR62## Slightly yellow oil ##STR63## Slightly yellow oil ##STR64## Slightly yellow oil ##STR65## Slightly yellow oil ##STR66## Slightly yellow oil ##STR67## Slightly yellow oil ##STR68## Slightly yellow oil ##STR69## Slightly yellow oil ##STR70## Slightly yellow oil ##STR71## Slightly yellow oil ##STR72## Slightly yellow oil ##STR73## Slightly yellow oil ##STR74## Slightly yellow oil ##STR75## Slightly yellow oil ##STR76## Slightly yellow oil ##STR77## Slightly yellow oil ##STR78## Slightly yellow oil ##STR79## m.p. 139.about. 140.degree. C. ##STR80## Slightly yellow oil ##STR81## Slightly yellow oil ##STR82## m.p. 144.about. 145.degree. C. ##STR83## m.p. 142.about. 143.degree. C. ##STR84## Slightly yellow oil ##STR85## Slightly yellow oil ##STR86## m.p. 160.about. 161.degree. C. ##STR87## Slightly yellow oil______________________________________ m.p.: melting point
REFERENCE EXAMPLE 5
Preparation of 3-methyl-5-phenyl-2-pyrazoline ##STR88##
17.1 g (342 mmol) of hydrazine monohydrate was dissolved in 500 ml of methanol. Then, 50 g (342 mmol) of trans-4-phenyl-3-buten-2-one dissolved in 100 ml of methanol was gradually dropwise added thereto under stirring within a range of from 5.degree. C. to 15.degree. C. Then, the mixture was stirred at room temperature for 30 hours, and methanol was distilled off under reduced pressure. The residue was distilled under reduced pressure to obtain 41.0 g of the desired 3-methyl-5-phenyl-2-pyrazoline.
Boiling point: 113.degree.-115.degree. C./0.2 mmHg.
The structural formulas and the physical properties or characteristics of the pyrazoline derivatives (3) prepared in the same manner as in Reference Example 5 are shown below:
______________________________________ ##STR89## ##STR90## ##STR91## ##STR92## ##STR93## ##STR94## ##STR95## ##STR96## ##STR97## ##STR98## ##STR99## ##STR100## ##STR101## ##STR102## ##STR103## ##STR104## ##STR105## ##STR106## ##STR107## ##STR108## ##STR109## ##STR110## ##STR111## ##STR112## ##STR113## ##STR114## ##STR115## ##STR116## ##STR117## ##STR118## ##STR119## ##STR120## ##STR121## ##STR122## ##STR123## ##STR124## ##STR125## ##STR126## ##STR127## ##STR128## ##STR129## ##STR130## ##STR131## ##STR132## ##STR133## ##STR134## ##STR135## ##STR136##______________________________________ b.p.: boiling point
EXAMPLE 1
Preparation of 1-[(N-dimethylsulfamoyl-N-ethylamino)sulfonylcarbamoyl]-3-methyl-5-phenyl-2-pyrazoline ##STR137##
A mixture comprising 3.3 g (9.4 mmol) of phenyl N-(N-dimethylsulfamoyl-N-ethylamino)sulfonyl]carbamate, 3.76 g (23.5 mmol) of 3-methyl-5-phenyl-2-pyrazoline and 30 ml of dry benzene was refluxed for 5 minutes. The mixture was left to cool, and then 50 ml of benzene was added thereto. The benzene layer was washed twice with dilute hydrochloric acid and then twice with water. Then, it was dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl.sub.3) and then washed sequentially with n-hexane and diethyl ether to obtain 2 g of the desired 1-[(N-dimethylsulfamoyl-N-ethylamino)sulfonylcarbamoyl]-3-methyl-5-phenyl-2-pyrazoline.
Melting point: 138.degree.-139.degree. C.
EXAMPLE 2
Preparation of 1-[(N-dimethylsulfamoyl-N-methylamino)sulfonylcarbamoyl]-3-methyl-5-(2-thienyl)-2-pyrazoline ##STR138##
A mixture comprising 1.69 g (5.0 mmol) of phenyl N-[(N-dimethylsulfamoyl-N-methylamino)sulfonyl]carbamate, 0.58 g (3.5 mmol) of 3-methyl-5-(2-thienyl)-2-pyrazoline and 10 ml of dry benzene, was refluxed for 10 minutes. The mixture was left to cool, and then benzene was distilled off under reduced pressure. The obtained residue was washed with n-hexane. Then, the residue was stirred together with diethyl ether. The precipitated crystalline product was isolated by suction filtration and then washed with diethyl ether to obtain 1.1 g of the desired 1-[(N-dimethylsulfamoyl-N-methylamino)sulfonylcarbamoyl]-3-methyl-5-(2-thienyl)-2-pyrazoline.
Melting point: 112.degree.-113.degree. C.
EXAMPLE 3
Preparation of 1-[(N-dimethylsulfamoyl-N-methoxyamino)sulfonylcarbamoyl]-3-methyl-5-phenyl-2-pyrazoline ##STR139##
4.24 g (12 mmol) of phenyl N-[(N-dimethylsulfamoyl-N-methoxyamino)sulfonyl]carbamate was dissolved in 30 ml of dry benzene, and 1.6 g (10 mmol) of 3-methyl-5-phenyl-2-pyrazoline was added thereto. The mixture was refluxed for 5 minutes. The mixture was left to cool, and the solvent was distilled off under reduced pressure. The residue was purified by reverse phase column chromatography (CH.sub.3 CN: H.sub.2 O=7:3) to obtain 1.0 g of the desired 1-[(N-dimethylsulfamoyl-N-methoxyamino)sulfonylcarbamoyl]-3-methyl-5-phenyl-2-pyrazoline.
Melting point: 104.degree.-105.degree. C.
EXAMPLE 4
Preparation of 1-[(N-(N-methyl-N-methoxyaminosulfonyl)-N-methylamino)sulfonylcarbamoyl]-3-methyl-5-phenyl-2-pyrazoline ##STR140##
A mixture comprising 1 g (2.83 mmol) of phenyl N-[(N-(N-methyl-N-methoxyaminosulfonyl)-N-methylamino)sulfonyl]-carbamate, 0.45 g (2.81 mmol) of 3-methyl-5-phenyl-2-pyrazoline and 30 ml of dry benzene was heated at 80.degree. C. for 5 minutes. The mixture was left to cool, and then the solvent was distilled off under reduced pressure. The residue was purified by reverse phase column chromatography (CH.sub.3 CN: H.sub.2 O=7:3) to obtain 0.5 g of the desired 1-[(N-(N-methyl-N-methoxyaminosulfonyl)-N-methyl-amino)sulfonylcarbamoyl]-3-methyl-5-phenyl-2-pyrazoline as glassy substance.
EXAMPLE 5
Preparation of 1-(2-methyl-tetrahydro-1,2,6-thiadiazine-1,1-dioxide-6-sulfonylcarbamoyl)-3-methyl-5-phenyl-2-pyrazoline ##STR141##
A mixture comprising 0.70 g (2 mmol) of phenyl N-(2-methyl-tetrahydro-1,2,6-thiadiazine-1,1-dioxide-6-sulfonyl)carbamate, 0.80 g (5 mmol) of 3-methyl-5-phenyl-2-pyrazoline and 30 ml of dry benzene, was refluxed for 5 minutes. The mixture was left to cool, and then 50 ml of benzene was added thereto. The benzene layer was washed three times with dilute hydrochloric acid and twice with water. Then, it was dried over anhydrous sodium sulfate, and then solvent was distilled off under reduced pressure. The obtained residue was washed sequentially with n-hexane and diethyl ether to obtain 0.7 g of the desired 1-(2-methyl-tetrahydro-1,2,6-thiadiazine-1,1- dioxide-6-sulfonylcarbamoyl)-3-methyl-5-phenyl-2-pyrazoline.
Melting point: 147.degree.-148.degree. C.
EXAMPLE 6
Preparation of 1-(2-methyl-tetrahydro-1,2,6-thiadiazine- 1,1-dioxide-6-sulfonylcarbamoyl)-3,5-dimethyl-5-phenyl-2-pyrazoline ##STR142##
A mixture comprising 8 g (22.9 mmol) of phenyl N-(2-methyl-tetrahydro-1,2,6-thiadiazine-1,1-dioxide-6-sulfonyl)carbamate, 5.1 g (29.3 mmol) of 3,5-dimethyl-5-phenyl-2-pyrazoline and 200 ml of dry benzene, was heated at 80.degree. C. for 5 minutes. The mixture was left to cool, and then solvent was distilled off under reduced pressure. The residue was washed with diethyl ether to obtain 6.2 g of the desired 1-(2-methyl-tetrahydro-1,2,6-thiadiazine-1,1-dioxide-6-sulfonylcarbamoyl)-3,5-dimethyl-5-phenyl-2-pyrazoline.
Melting point: 151.degree.-154.degree. C.
The structural formulas and the physical properties or characteristics of the compounds prepared in the same manner as in Examples 1 to 6 are shown below: ##STR143##
Examples of compounds covered by the present invention including those prepared in the preceding Examples will be given in the following Tables 1 to 14 and Tables 1A to 14A. However, it should be understood that the compounds of the present invention are not limited to such specific Examples.
The symbols in the Tables have the following meanings.
Me: methyl group, Et: ethyl group, Pr-n: n-propyl group, Pr-i: isopropyl group, cyc-Pr: cyclopropyl group, Bu-n: n-butyl group, Bu-i: isobutyl group, Bu-sec: secondary butyl group, Bu-t: tert-butyl group, cyc-Bu: cyclobutyl group, Pen-n: n-pentyl group, cyc-Hex: cyclohexyl group, Ph: phenyl group, Gn is the same as the above G, and Ga, Gb and Gc have the following meanings.
Ga=G1-G643 (i.e. it means any one of G1 to G643.)
Gb=G1 -G72 and G102-G136 (i.e. it means any one of G1 to G72 and G102 to G136 .)
Gc=G1 -G35 and G102 -G136 (i.e. it means any one of G1 to G35 and G102 to G136 .) ##STR144##
TABLE 1______________________________________R.sup.11 R.sup.12 R.sup.13 Gn______________________________________H Me Me GaH Me Et GaH Me Ph GaH Me PhCH.sub.2 GaH Et Et GaH Pr-n Pr-n GbH (CH.sub.2).sub.4 GaH (CH.sub.2).sub.5 GaMe H Me GcMe H Et GcMe Me Me GaMe Me Et GaMe Me Pr-n GbMe Me Pr-i GbMe Me Bu-n GbMe Me Ph GaMe Me Ph-2-Cl GbMe Me Ph-2-CO.sub.2 Me GbMe Me Ph-2-OMe GbMe Me Ph-2-CF.sub.3 GbMe Me Ph-2-NO.sub.2 GbMe Me Ph-2-Me GbMe Me PhCH.sub.2 GaMe Et Et GaMe Pr-n Pr-n GbMe (CH.sub.2).sub.4 GaMe (CH.sub.2).sub.5 GaEt H Me GcEt H Et GcEt Me Me GaEt Me Et GaEt Me Pr-n GbEt Me Pr-i GbEt Me Bu-n GbEt Me Ph GaEt Me Ph-2-Cl GbEt Me Ph-2-CO.sub.2 Me GbEt Me Ph-2-OMe GbEt Me Ph-2-CF.sub.3 GbEt Me Ph-2-NO.sub.2 GbEt Me Ph-2-Me GbEt Me PhCH.sub.2 GaEt Et Et GaEt Pr-n Pr-n GbEt (CH.sub.2).sub.4 GaEt (CH.sub.2).sub.5 GaPr-n H Me GcPr-n H Et GcPr-n Me Me GaPr-n Me Et GaPr-n Me Pr-n GbPr-n Me Pr-i GbPr-n Me Bu-n GbPr-n Me Ph GaPr-n Me Ph-2-Cl GbPr-n Me Ph-2-CO.sub.2 Me GbPr-n Me Ph-2-OMe GbPr-n Me Ph-2-CF.sub.3 GbPr-n Me Ph-2-NO.sub.2 GbPr-n Me Ph-2-Me GbPr-n Me PhCH.sub.2 GaPr-n Et Et GaPr-n Pr-n Pr-n GbPr-n (CH.sub.2).sub.4 GaPr-n (CH.sub.2).sub.5 GaPr-i H Me GcPr-i H Et GcPr-i Me Me GaPr-i Me Et GaPr-i Me Pr-n GbPr-i Me Pr-i GbPr-i Me Bu-n GbPr-i Me Ph GaPr-i Me Ph-2-Cl GbPr-i Me Ph-2-CO.sub.2 Me GbPr-i Me Ph-2-OMe GbPr-i Me Ph-2-CF.sub.3 GbPr-i Me Ph-2-NO.sub.2 GbPr-i Me Ph-2-Me GbPr-i Me PhCH.sub.2 GaPr-i Et Et GaPr-i Pr-n Pr-n GbPr-i (CH.sub.2).sub.4 GaPr-i (CH.sub.2).sub.5 Gacyc-Pr Me Me Gacyc-Pr Me Et Gacyc-Pr Me Ph Gacyc-Pr Me PhCH.sub.2 Gacyc-Pr Et Et Gacyc-Pr Pr-n Pr-n Gbcyc-Pr (CH.sub.2).sub.4 Gacyc-Pr (CH.sub.2).sub.5 Gacyc-PrCH.sub.2 Me Me Gacyc-PrCH.sub.2 Me Et Gacyc-PrCH.sub.2 Me Ph Gacyc-PrCH.sub.2 Me PhCH.sub.2 Gacyc-PrCH.sub.2 Et Et Gacyc-PrCH.sub.2 Pr-n Pr-n Gbcyc-PrCH.sub.2 (CH.sub.2).sub.4 Gacyc-PrCH.sub.2 (CH.sub.2).sub.5 GaBu-n H Me GcBu-n H Et GcBu-n Me Me GaBu-n Me Et GaBu-n Me Pr-n GbBu-n Me Pr-i GbBu-n Me Bu-n GbBu-n Me Ph GaBu-n Me Ph-2-Cl GbBu-n Me Ph-2-CO.sub.2 Me GbBu-n Me Ph-2-OMe GbBu-n Me Ph-2-CF.sub.3 GbBu-n Me Ph-2-NO.sub.2 GbBu-n Me Ph-2-Me GbBu-n Me PhCH.sub.2 GaBu-n Et Et GaBu-n Pr-n Pr-n GbBu-n (CH.sub.2).sub.4 GaBu-n (CH.sub.2).sub.5 GaBu-sec H Me GcBu-sec H Et GcBu-sec Me Me GaBu-sec Me Et GaBu-sec Me Ph GaBu-sec Me PhCH.sub.2 GaBu-sec Et Et GaBu-sec Pr-n Pr-n GbBu-sec (CH.sub.2).sub.4 GaBu-sec (CH.sub.2).sub.5 GaBu-t H Me GcBu-t H Et GcBu-t Me Me GaBu-t Me Et GaBu-t Me Ph GaBu-t Me PhCH.sub.2 GaBu-t Et Et GaBu-t Pr-n Pr-n GbBu-t (CH.sub.2).sub.4 GaBu-t (CH.sub.2 ).sub.5 GaCH.sub.2CHCH.sub.2 H Me GcCH.sub.2CHCH.sub.2 H Et GcCH.sub.2CHCH.sub.2 Me Me GaCH.sub.2CHCH.sub.2 Me Et GaCH.sub.2CHCH.sub.2 Me Pr-n GbCH.sub.2CHCH.sub.2 Me Pr-i GbCH.sub.2CHCH.sub.2 Me Bu-n GbCH.sub.2CHCH.sub.2 Me Ph GaCH.sub.2CHCH.sub.2 Me Ph-2-Cl GbCH.sub.2CHCH.sub.2 Me Ph-2-CO.sub.2 Me GbCH.sub.2CHCH.sub.2 Me Ph-2-OMe GbCH.sub.2CHCH.sub.2 Me Ph-2-CF.sub.3 GbCH.sub.2CHCH.sub.2 Me Ph-2-NO.sub.2 GbCH.sub.2CHCH.sub.2 Me Ph-2-Me GbCH.sub.2CHCH.sub.2 Me PhCH.sub.2 GaCH.sub.2CHCH.sub.2 Et Et GaCH.sub.2CHCH.sub.2 Pr-n Pr-n GbCH.sub.2CHCH.sub.2 (CH.sub.2).sub.4 GaCH.sub.2CHCH.sub.2 (CH.sub.2).sub.5 GaCH CCH.sub.2 H Me GcCH CCH.sub.2 H Et GcCH CCH.sub.2 Me Me GaCH CCH.sub.2 Me Et GaCH CCH.sub.2 Me Pr-n GbCH CCH.sub.2 Me Pr-i GbCH CCH.sub.2 Me Bu-n GbCH CCH.sub.2 Me Ph GaCH CCH.sub.2 Me Ph-2-Cl GbCH CCH.sub.2 Me Ph-2-CO.sub.2 Me GbCH CCH.sub.2 Me Ph-2-OMe GbCH CCH.sub.2 Me Ph-2-CF.sub.3 GbCH CCH.sub.2 Me Ph-2-NO.sub.2 GbCH CCH.sub.2 Me Ph-2-Me GbCH CCH.sub.2 Me PhCH.sub.2 GaCH CCH.sub.2 Et Et GaCH CCH.sub.2 Pr-n Pr-n GbCH CCH.sub.2 (CH.sub.2).sub.4 GaCH CCH.sub.2 (CH.sub.2).sub.5 GaMeOCH.sub.2 Me Me GaMeOCH.sub.2 Me Et GaMeOCH.sub.2 Me Ph GaMeOCH.sub.2 Me PhCH.sub.2 GaMeOCH.sub.2 Et Et GaMeOCH.sub.2 Pr-n Pr-n GbMeOCH.sub.2 (CH.sub.2).sub.4 GaMeOCH.sub.2 (CH.sub.2).sub.5 GaEtOCH.sub.2 Me Me GaEtOCH.sub.2 Me Et GaEtOCH.sub.2 Me Ph GaEtOCH.sub.2 Me PhCH.sub.2 GaEtOCH.sub.2 Et Et GaEtOCH.sub.2 Pr-n Pr-n GbEtOCH.sub.2 (CH.sub.2).sub.4 GaEtOCH.sub.2 (CH.sub.2).sub.5 GaMeOCH.sub.2 CH.sub.2 H Me GcMeOCH.sub.2 CH.sub.2 H Et GcMeOCH.sub.2 CH.sub.2 Me Me GaMeOCH.sub.2 CH.sub.2 Me Et GaMeOCH.sub.2 CH.sub.2 Me Pr-n GbMeOCH.sub.2 CH.sub.2 Me Pr-i GbMeOCH.sub.2 CH.sub.2 Me Bu-n GbMeOCH.sub.2 CH.sub.2 Me Ph GaMeOCH.sub.2 CH.sub.2 Me Ph-2-Cl GbMeOCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbMeOCH.sub.2 CH.sub.2 Me Ph-2-OMe GbMeOCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbMeOCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbMeOCH.sub.2 CH.sub.2 Me Ph-2-Me GbMeOCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaMeOCH.sub.2 CH.sub.2 Et Et GaMeOCH.sub.2 CH.sub.2 Pr-n Pr-n GbMeOCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaMeOCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaEtOCH.sub.2 CH.sub.2 H Me GcEtOCH.sub.2 CH.sub.2 H Et GcEtOCH.sub.2 CH.sub.2 Me Me GaEtOCH.sub.2 CH.sub.2 Me Et GaEtOCH.sub.2 CH.sub.2 Me Pr-n GbEtOCH.sub.2 CH.sub.2 Me Pr-i GbEtOCH.sub.2 CH.sub.2 Me Bu-n GbEtOCH.sub.2 CH.sub.2 Me Ph GaEtOCH.sub.2 CH.sub.2 Me Ph-2-Cl GbEtOCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbEtOCH.sub.2 CH.sub.2 Me Ph-2-OMe GbEtOCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbEtOCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbEtOCH.sub.2 CH.sub.2 Me Ph-2-Me GbEtOCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaEtOCH.sub.2 CH.sub.2 Et Et GaEtOCH.sub.2 CH.sub.2 Pr-n Pr-n GbEtOCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtOCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaMeOCH.sub.2 (CH.sub.3)CH H Me GcMeOCH.sub.2 (CH.sub.3)CH H Et GcMeOCH.sub.2 (CH.sub.3)CH Me Me GaMeOCH.sub.2 (CH.sub.3)CH Me Et GaMeOCH.sub.2 (CH.sub.3)CH Me Pr-n GbMeOCH.sub.2 (CH.sub.3)CH Me Pr-i GbMeOCH.sub.2 (CH.sub.3)CH Me Bu-n GbMeOCH.sub.2 (CH.sub.3)CH Me Ph GaMeOCH.sub.2 (CH.sub.3)CH Me Ph-2-Cl GbMeOCH.sub.2 (CH.sub.3)CH Me Ph-2-CO.sub.2 Me GbMeOCH.sub.2 (CH.sub.3)CH Me Ph-2-OMe GbMeOCH.sub.2 (CH.sub.3)CH Me Ph-2-CF.sub.3 GbMeOCH.sub.2 (CH.sub.3)CH Me Ph-2-NO.sub.2 GbMeOCH.sub.2 (CH.sub. 3)CH Me Ph-2-Me GbMeOCH.sub.2 (CH.sub.3)CH Me PhCH.sub.2 GaMeOCH.sub.2 (CH.sub.3)CH Et Et GaMeOCH.sub.2 (CH.sub.3)CH Pr-n Pr-n GbMeOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GaMeOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.5 GaEtOCH.sub.2 (CH.sub.3)CH H Me GcEtOCH.sub.2 (CH.sub.3)CH H Et GcEtOCH.sub.2 (CH.sub.3)CH Me Me GaEtOCH.sub.2 (CH.sub.3)CH Me Et GaEtOCH.sub.2 (CH.sub.3)CH Me Pr-n GbEtOCH.sub.2 (CH.sub.3)CH Me Pr-i GbEtOCH.sub.2 (CH.sub.3)CH Me Bu-n GbEtOCH.sub.2 (CH.sub.3)CH Me Ph GaEtOCH.sub.2 (CH.sub.3)CH Me Ph-2-Cl GbEtOCH.sub.2 (CH.sub.3)CH Me Ph-2-CO.sub.2 Me GbEtOCH.sub.2 (CH.sub.3)CH Me Ph-2-OMe GbEtOCH.sub.2 (CH.sub.3)CH Me Ph-2-CF.sub.3 GbEtOCH.sub.2 (CH.sub.3)CH Me Ph-2-NO.sub.2 GbEtOCH.sub.2 (CH.sub.3)CH Me Ph-2-Me GbEtOCH.sub.2 (CH.sub.3)CH Me PhCH.sub.2 GaEtOCH.sub.2 (CH.sub.3)CH Et Et GaEtOCH.sub.2 (CH.sub.3 )CH Pr-n Pr-n GbEtOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GaEtOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.5 GaCHF.sub.2 OCH.sub.2 H Me GcCHF.sub.2 OCH.sub.2 H Et GcCHF.sub.2 OCH.sub.2 Me Me GaCHF.sub.2 OCH.sub.2 Me Et GaCHF.sub.2 OCH.sub.2 Me Pr-n GbCHF.sub.2 OCH.sub.2 Me Pr-i GbCHF.sub.2 OCH.sub.2 Me Bu-n GbCHF.sub.2 OCH.sub.2 Me Ph GaCHF.sub.2 OCH.sub.2 Me Ph-2-Cl GbCHF.sub.2 OCH.sub.2 Me Ph-2-CO.sub.2 Me GbCHF.sub.2 OCH.sub.2 Me Ph-2-OMe GbCHF.sub.2 OCH.sub.2 Me Ph-2-CF.sub.3 GbCHF.sub.2 OCH.sub.2 Me Ph-2-NO.sub.2 GbCHF.sub.2 OCH.sub.2 Me Ph-2-Me GbCHF.sub.2 OCH.sub.2 Me PhCH.sub.2 GaCHF.sub.2 OCH.sub.2 Et Et GaCHF.sub.2 OCH.sub.2 Pr-n Pr-n GbCHF.sub.2 OCH.sub.2 (CH.sub.2).sub.4 GaCHF.sub.2 OCH.sub.2 (CH.sub.2).sub.5 GaMeSCH.sub.2 Me Me GaMeSCH.sub.2 Me Et GaMeSCH.sub. 2 Me Ph GaMeSCH.sub.2 Me PhCH.sub.2 GaMeSCH.sub.2 Et Et GaMeSCH.sub.2 Pr-n Pr-n GbMeSCH.sub.2 (CH.sub.2).sub.4 GaMeSCH.sub.2 (CH.sub.2).sub.5 GaEtSCH.sub.2 Me Me GaEtSCH.sub.2 Me Et GaEtSCH.sub.2 Me Ph GaEtSCH.sub.2 Me PhCH.sub.2 GaEtSCH.sub.2 Et Et GaEtSCH.sub.2 Pr-n Pr-n GbEtSCH.sub.2 (CH.sub.2).sub.4 GaEtSCH.sub.2 (CH.sub.2).sub.5 GaMeSCH.sub.2 CH.sub.2 H Me GcMeSCH.sub.2 CH.sub.2 H Et GcMeSCH.sub.2 CH.sub.2 Me Me GaMeSCH.sub.2 CH.sub.2 Me Et GaMeSCH.sub.2 CH.sub.2 Me Pr-n GbMeSCH.sub.2 CH.sub.2 Me Pr-i GbMeSCH.sub.2 CH.sub.2 Me Bu-n GbMeSCH.sub.2 CH.sub.2 Me Ph GaMeSCH.sub.2 CH.sub.2 Me Ph-2-Cl GbMeSCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbMeSCH.sub.2 CH.sub.2 Me Ph-2-OMe GbMeSCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbMeSCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbMeSCH.sub.2 CH.sub. 2 Me Ph-2-Me GbMeSCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaMeSCH.sub.2 CH.sub.2 Et Et GaMeSCH.sub.2 CH.sub.2 Pr-n Pr-n GbMeSCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaMeSCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaEtSCH.sub.2 CH.sub.2 H Me GcEtSCH.sub.2 CH.sub.2 H Et GcEtSCH.sub.2 CH.sub.2 Me Me GaEtSCH.sub.2 CH.sub.2 Me Et GaEtSCH.sub.2 CH.sub.2 Me Pr-n GbEtSCH.sub.2 CH.sub.2 Me Pr-i GbEtSCH.sub.2 CH.sub.2 Me Bu-n GbEtSCH.sub.2 CH.sub.2 Me Ph GaEtSCH.sub.2 CH.sub.2 Me Ph-2-Cl GbEtSCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbEtSCH.sub.2 CH.sub.2 Me Ph-2-OMe GbEtSCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbEtSCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbEtSCH.sub.2 CH.sub.2 Me Ph-2-Me GbEtSCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaEtSCH.sub.2 CH.sub.2 Et Et GaEtSCH.sub.2 CH.sub.2 Pr-n Pr-n GbEtSCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtSCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaMeSO.sub.2 CH.sub.2 Me Me GaMeSO.sub.2 CH.sub.2 Me Et GaMeSO.sub.2 CH.sub.2 Me Ph GaMeSO.sub.2 CH.sub.2 Me PhCH.sub.2 GaMeSO.sub.2 CH.sub.2 Et Et GaMeSO.sub.2 CH.sub.2 Pr-n Pr-n GbMeSO.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaMeSO.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaEtSO.sub.2 CH.sub.2 Me Me GaEtSO.sub.2 CH.sub.2 Me Et GaEtSO.sub.2 CH.sub.2 Me Ph GaEtSO.sub.2 CH.sub.2 Me PhCH.sub.2 GaEtSO.sub.2 CH.sub.2 Et Et GaEtSO.sub.2 CH.sub.2 Pr-n Pr-n GbEtSO.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtSO.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaMeSO.sub.2 CH.sub.2 CH.sub.2 H Me GcMeSO.sub.2 CH.sub.2 CH.sub.2 H Et GcMeSO.sub.2 CH.sub.2 CH.sub.2 Me Me GaMeSO.sub.2 CH.sub.2 CH.sub.2 Me Et GaMeSO.sub.2 CH.sub.2 CH.sub.2 Me Pr-n GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Pr-i GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Bu-n GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Ph GaMeSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-Cl GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-OMe GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-Me GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me PhCH.sub.2 GaMeSO.sub.2 CH.sub.2 CH.sub.2 Et Et GaMeSO.sub.2 CH.sub.2 CH.sub.2 Pr-n Pr-n GbMeSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaMeSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaEtSO.sub.2 CH.sub.2 CH.sub.2 H Me GcEtSO.sub.2 CH.sub.2 CH.sub.2 H Et GcEtSO.sub.2 CH.sub.2 CH.sub.2 Me Me GaEtSO.sub.2 CH.sub.2 CH.sub.2 Me Et GaEtSO.sub.2 CH.sub.2 CH.sub.2 Me Pr-n GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Pr-i GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Bu-n GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Ph GaEtSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-Cl GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-OMe GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Ph-2-Me GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me PhCH.sub.2 GaEtSO.sub.2 CH.sub.2 CH.sub.2 Et Et GaEtSO.sub.2 CH.sub.2 CH.sub.2 Pr-n Pr-n GbEtSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaFCH.sub.2 Me Me GaFCH.sub.2 Me Et GaFCH.sub.2 Me Ph GaFCH.sub.2 Me PhCH.sub.2 GaFCH.sub.2 Et Et GaFCH.sub.2 Pr-n Pr-n GbFCH.sub.2 (CH.sub.2).sub.4 GaFCH.sub.2 (CH.sub.2).sub.5 GaClCH.sub.2 Me Me GaClCH.sub.2 Me Et GaClCH.sub.2 Me Ph GaClCH.sub.2 Me PhCH.sub.2 GaClCH.sub.2 Et Et GaClCH.sub.2 Pr-n Pr-n GbClCH.sub.2 (CH.sub.2).sub.4 GaClCH.sub.2 (CH.sub.2).sub.5 GaBrCH.sub.2 Me Me GaBrCH.sub.2 Me Et GaBrCH.sub.2 Me Ph GaBrCH.sub.2 Me PhCH.sub.2 GaBrCH.sub.2 Et Et GaBrCH.sub.2 Pr-n Pr-n GbBrCH.sub.2 (CH.sub.2).sub.4 GaBrCH.sub.2 (CH.sub.2).sub.5 GaICH.sub.2 Me Me GaICH.sub.2 Me Et GaICH.sub.2 Me Ph GaICH.sub.2 Me PhCH.sub.2 GaICH.sub.2 Et Et GaICH.sub.2 Pr-n Pr-n GbICH.sub.2 (CH.sub.2).sub.4 GaICH.sub.2 (CH.sub.2).sub.5 GaFCH.sub.2 CH.sub.2 H Me GcFCH.sub.2 CH.sub.2 H Et GcFCH.sub.2 CH.sub.2 Me Me GaFCH.sub.2 CH.sub.2 Me Et GaFCH.sub.2 CH.sub.2 Me Pr-n GbFCH.sub.2 CH.sub.2 Me Pr-i GbFCH.sub.2 CH.sub.2 Me Bu-n GbFCH.sub.2 CH.sub.2 Me Ph GaFCH.sub.2 CH.sub.2 Me Ph-2-Cl GbFCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbFCH.sub.2 CH.sub.2 Me Ph-2-OMe GbFCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbFCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbFCH.sub.2 CH.sub.2 Me Ph-2-Me GbFCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaFCH.sub.2 CH.sub.2 Et Et GaFCH.sub.2 CH.sub.2 Pr-n Pr-n GbFCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaFCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaClCH.sub.2 CH.sub.2 H Me GcClCH.sub.2 CH.sub.2 H Et GcClCH.sub.2 CH.sub.2 Me Me GaClCH.sub.2 CH.sub.2 Me Et GaClCH.sub.2 CH.sub.2 Me Pr-n GbClCH.sub.2 CH.sub.2 Me Pr-i GbClCH.sub.2 CH.sub.2 Me Bu-n GbClCH.sub.2 CH.sub.2 Me Ph GaClCH.sub.2 CH.sub.2 Me Ph-2-Cl GbClCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbClCH.sub.2 CH.sub.2 Me Ph-2-OMe GbClCH.sub. 2 CH.sub.2 Me Ph-2-CF.sub.3 GbClCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbClCH.sub.2 CH.sub.2 Me Ph-2-Me GbClCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaClCH.sub.2 CH.sub.2 Et Et GaClCH.sub.2 CH.sub.2 Pr-n Pr-n GbClCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaClCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaBrCH.sub.2 CH.sub.2 H Me GcBrCH.sub.2 CH.sub.2 H Et GcBrCH.sub.2 CH.sub.2 Me Me GaBrCH.sub.2 CH.sub.2 Me Et GaBrCH.sub.2 CH.sub.2 Me Pr-n GbBrCH.sub.2 CH.sub.2 Me Pr-i GbBrCH.sub.2 CH.sub.2 Me Bu-n GbBrCH.sub.2 CH.sub.2 Me Ph GaBrCH.sub.2 CH.sub.2 Me Ph-2-Cl GbBrCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbBrCH.sub.2 CH.sub.2 Me Ph-2-OMe GbBrCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbBrCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbBrCH.sub.2 CH.sub.2 Me Ph-2-Me GbBrCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaBrCH.sub.2 CH.sub.2 Et Et GaBrCH.sub.2 CH.sub.2 Pr-n Pr-n GbBrCH.sub. 2 CH.sub.2 (CH.sub.2).sub.4 GaBrCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaICH.sub.2 CH.sub.2 H Me GcICH.sub.2 CH.sub.2 H Et GcICH.sub.2 CH.sub.2 Me Me GaICH.sub.2 CH.sub.2 Me Et GaICH.sub.2 CH.sub.2 Me Pr-n GbICH.sub.2 CH.sub.2 Me Pr-i GbICH.sub.2 CH.sub.2 Me Bu-n GbICH.sub.2 CH.sub.2 Me Ph GaICH.sub.2 CH.sub.2 Me Ph-2-Cl GbICH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbICH.sub.2 CH.sub.2 Me Ph-2-OMe GbICH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbICH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbICH.sub.2 CH.sub.2 Me Ph-2-Me GbICH.sub.2 CH.sub.2 Me PhCH.sub.2 GaICH.sub.2 CH.sub.2 Et Et GaICH.sub.2 CH.sub.2 Pr-n Pr-n GbICH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaICH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaFCH.sub.2 (CH.sub.3)CH Me Me GaFCH.sub.2 (CH.sub.3)CH Me Et GaFCH.sub.2 (CH.sub. 3)CH Me Ph GaFCH.sub.2 (CH.sub.3)CH Me PhCH.sub.2 GaFCH.sub.2 (CH.sub.3)CH Et Et GaFCH.sub.2 (CH.sub.3)CH Pr-n Pr-n GbFCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GaFCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.5 GaClCH.sub.2 (CH.sub.3)CH Me Me GaClCH.sub.2 (CH.sub.3)CH Me Et GaClCH.sub.2 (CH.sub.3)CH Me Ph GaClCH.sub.2 (CH.sub.3)CH Me PhCH.sub.2 GaClCH.sub.2 (CH.sub.3)CH Et Et GaClCH.sub.2 (CH.sub.3)CH Pr-n Pr-n GbClCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GaClCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.5 GaBrCH.sub.2 (CH.sub.3)CH Me Me GaBrCH.sub.2 (CH.sub.3)CH Me Et GaBrCH.sub.2 (CH.sub.3)CH Me Ph GaBrCH.sub.2 (CH.sub.3)CH Me PhCH.sub.2 GaBrCH.sub.2 (CH.sub.3)CH Et Et GaBrCH.sub.2 (CH.sub.3)CH Pr-n Pr-n GbBrCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GaBrCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.5 GaICH.sub.2 (CH.sub.3)CH Me Me GaICH.sub.2 (CH.sub.3)CH Me Et GaICH.sub.2 (CH.sub.3)CH Me Ph GaICH.sub.2 (CH.sub.3)CH Me PhCH.sub.2 GaICH.sub.2 (CH.sub.3)CH Et Et GaICH.sub.2 (CH.sub.3)CH Pr-n Pr-n GbICH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GaICH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.5 GaCF.sub.3 CH.sub.2 H Me GcCF.sub.3 CH.sub.2 H Et GcCF.sub.3 CH.sub.2 Me Me GaCF.sub.3 CH.sub.2 Me Et GaCF.sub.3 CH.sub.2 Me Pr-n GbCF.sub.3 CH.sub.2 Me Pr-i GbCF.sub.3 CH.sub.2 Me Bu-n GbCF.sub.3 CH.sub.2 Me Ph GaCF.sub.3 CH.sub.2 Me Ph-2-Cl GbCF.sub.3 CH.sub.2 Me Ph-2-CO.sub.2 Me GbCF.sub.3 CH.sub.2 Me Ph-2-OMe GbCF.sub.3 CH.sub.2 Me Ph-2-CF.sub.3 GbCF.sub.3 CH.sub.2 Me Ph-2-NO.sub.2 GbCF.sub.3 CH.sub.2 Me Ph-2-Me GbCF.sub.3 CH.sub.2 Me PhCH.sub.2 GaCF.sub.3 CH.sub.2 Et Et GaCF.sub.3 CH.sub.2 Pr-n Pr-n GbCF.sub.3 CH.sub.2 (CH.sub.2).sub.4 GaCF.sub.3 CH.sub.2 (CH.sub.2).sub.5 GaNCCH.sub.2 H Me GcNCCH.sub.2 H Et GcNCCH.sub.2 Me Me GaNCCH.sub.2 Me Et GaNCCH.sub.2 Me Pr-n GbNCCH.sub.2 Me Pr-i GbNCCH.sub.2 Me Bu-n GbNCCH.sub.2 Me Ph GaNCCH.sub.2 Me Ph-2-Cl GbNCCH.sub.2 Me Ph-2-CO.sub.2 Me GbNCCH.sub.2 Me Ph-2-OMe GbNCCH.sub.2 Me Ph-2-CF.sub.3 GbNCCH.sub.2 Me Ph-2-NO.sub.2 GbNCCH.sub.2 Me Ph-2-Me GbNCCH.sub.2 Me PhCH.sub.2 GaNCCH.sub.2 Et Et GaNCCH.sub.2 Pr-n Pr-n GbNCCH.sub.2 (CH.sub.2).sub.4 GaNCCH.sub.2 (CH.sub.2).sub.5 GaNCCH.sub.2 CH.sub.2 H Me GcNCCH.sub.2 CH.sub.2 H Et GcNCCH.sub.2 CH.sub.2 Me Me GaNCCH.sub.2 CH.sub.2 Me Et GaNCCH.sub.2 CH.sub.2 Me Pr-n GbNCCH.sub.2 CH.sub.2 Me Pr-i GbNCCH.sub.2 CH.sub.2 Me Bu-n GbNCCH.sub.2 CH.sub.2 Me Ph GaNCCH.sub.2 CH.sub.2 Me Ph-2-Cl GbNCCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbNCCH.sub.2 CH.sub.2 Me Ph-2-OMe GbNCCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbNCCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbNCCH.sub.2 CH.sub.2 Me Ph-2-Me GbNCCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaNCCH.sub.2 CH.sub.2 Et Et GaNCCH.sub.2 CH.sub.2 Pr-n Pr-n GbNCCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaNCCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaMeO.sub.2 CCH.sub.2 H Me GcMeO.sub.2 CCH.sub.2 H Et GcMeO.sub.2 CCH.sub.2 Me Me GaMeO.sub.2 CCH.sub.2 Me Et GaMeO.sub.2 CCH.sub.2 Me Pr-n GbMeO.sub.2 CCH.sub.2 Me Pr-i GbMeO.sub.2 CCH.sub.2 Me Bu-n GbMeO.sub.2 CCH.sub.2 Me Ph GaMeO.sub.2 CCH.sub.2 Me Ph-2-Cl GbMeO.sub.2 CCH.sub.2 Me Ph-2-CO.sub.2 Me GbMeO.sub.2 CCH.sub.2 Me Ph-2-OMe GbMeO.sub.2 CCH.sub.2 Me Ph-2-CF.sub.3 GbMeO.sub.2 CCH.sub.2 Me Ph-2-NO.sub.2 GbMeO.sub.2 CCH.sub.2 Me Ph-2-Me GbMeO.sub.2 CCH.sub.2 Me PhCH.sub.2 GaMeO.sub.2 CCH.sub.2 Et Et GaMeO.sub.2 CCH.sub.2 Pr-n Pr-n GbMeO.sub.2 CCH.sub.2 (CH.sub.2).sub.4 GaMeO.sub.2 CCH.sub.2 (CH.sub.2).sub.5 GaEtO.sub.2 CCH.sub.2 H Me GcEtO.sub.2 CCH.sub.2 H Et GcEtO.sub.2 CCH.sub.2 Me Me GaEtO.sub.2 CCH.sub.2 Me Et GaEtO.sub.2 CCH.sub.2 Me Pr-n GbEtO.sub.2 CCH.sub.2 Me Pr-i GbEtO.sub.2 CCH.sub.2 Me Bu-n GbEtO.sub.2 CCH.sub.2 Me Ph GaEtO.sub.2 CCH.sub.2 Me Ph-2-Cl GbEtO.sub.2 CCH.sub.2 Me Ph-2-CO.sub.2 Me GbEtO.sub.2 CCH.sub.2 Me Ph-2-OMe GbEtO.sub.2 CCH.sub.2 Me Ph-2-CF.sub.3 GbEtO.sub.2 CCH.sub.2 Me Ph-2-NO.sub.2 GbEtO.sub.2 CCH.sub.2 Me Ph-2-Me GbEtO.sub.2 CCH.sub.2 Me PhCH.sub.2 GaEtO.sub.2 CCH.sub.2 Et Et GaEtO.sub.2 CCH.sub.2 Pr-n Pr-n GbEtO.sub.2 CCH.sub.2 (CH.sub.2).sub.4 GaEtO.sub.2 CCH.sub.2 (CH.sub.2).sub.5 GaPr-nO.sub.2 CCH.sub.2 Me Me GaPr-nO.sub.2 CCH.sub.2 Me Et GaPr-nO.sub.2 CCH.sub.2 Me Ph GaPr-nO.sub.2 CCH.sub.2 Me PhCH.sub.2 GaPr-nO.sub.2 CCH.sub.2 Et Et GaPr-nO.sub.2 CCH.sub.2 Pr-n Pr-n GbPr-nO.sub.2 CCH.sub.2 (CH.sub.2).sub.4 GaPr-nO.sub.2 CCH.sub.2 (CH.sub.2).sub.5 GaMeO.sub.2 CCH.sub.2 CH.sub.2 H Me GcMeO.sub.2 CCH.sub.2 CH.sub.2 H Et GcMeO.sub.2 CCH.sub.2 CH.sub.2 Me Me GaMeO.sub.2 CCH.sub.2 CH.sub.2 Me Et GaMeO.sub.2 CCH.sub.2 CH.sub.2 Me Pr-n GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Pr-i GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Bu-n GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Ph GaMeO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-Cl GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-OMe GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-Me GbMeO.sub.2 CCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaMeO.sub.2 CCH.sub.2 CH.sub.2 Et Et GaMeO.sub.2 CCH.sub.2 CH.sub.2 Pr-n Pr-n GbMeO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaMeO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaEtO.sub.2 CCH.sub.2 CH.sub.2 H Me GcEtO.sub.2 CCH.sub.2 CH.sub.2 H Et GcEtO.sub.2 CCH.sub.2 CH.sub.2 Me Me GaEtO.sub.2 CCH.sub.2 CH.sub.2 Me Et GaEtO.sub.2 CCH.sub.2 CH.sub.2 Me Pr-n GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Pr-i GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Bu-n GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Ph GaEtO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-Cl GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-CO.sub.2 Me GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-OMe GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-CF.sub.3 GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-NO.sub.2 GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me Ph-2-Me GbEtO.sub.2 CCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaEtO.sub.2 CCH.sub.2 CH.sub.2 Et Et GaEtO.sub.2 CCH.sub.2 CH.sub.2 Pr-n Pr-n GbEtO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaPr-nO.sub.2 CCH.sub.2 CH.sub.2 Me Me GaPr-nO.sub.2 CCH.sub.2 CH.sub.2 Me Et GaPr-nO.sub.2 CCH.sub.2 CH.sub.2 Me Ph GaPr-nO.sub.2 CCH.sub.2 CH.sub.2 Me PhCH.sub.2 GaPr-nO.sub.2 CCH.sub.2 CH.sub.2 Et Et GaPr-nO.sub.2 CCH.sub.2 CH.sub.2 Pr-n Pr-n GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaPr-nO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GaMeCOCH.sub.2 Me Me GaMeCOCH.sub.2 Me Et GaMeCOCH.sub.2 Me Ph GaMeCOCH.sub.2 Me PhCH.sub.2 GaMeCOCH.sub.2 Et Et GaMeCOCH.sub.2 Pr-n Pr-n GbMeCOCH.sub.2 (CH.sub.2).sub.4 GaMeCOCH.sub.2 (CH.sub.2).sub.5 GaEtCOCH.sub.2 Me Me GaEtCOCH.sub.2 Me Et GaEtCOCH.sub.2 Me Ph GaEtCOCH.sub.2 Me PhCH.sub.2 GaEtCOCH.sub.2 Et Et GaEtCOCH.sub.2 Pr-n Pr-n GbEtCOCH.sub.2 (CH.sub.2).sub.4 GaEtCOCH.sub.2 (CH.sub.2).sub.5 GaPhCH.sub.2 H Me GcPhCH.sub.2 H Et GcPhCH.sub.2 Me Me GaPhCH.sub.2 Me Et GaPhCH.sub.2 Me Pr-n GbPhCH.sub.2 Me Pr-i GbPhCH.sub.2 Me Bu-n GbPhCH.sub.2 Me Ph GaPhCH.sub.2 Me Ph-2-Cl GbPhCH.sub.2 Me Ph-2-CO.sub.2 Me GbPhCH.sub.2 Me Ph-2-OMe GbPhCH.sub.2 Me Ph-2-CF.sub.3 GbPhCH.sub.2 Me Ph-2-NO.sub.2 GbPhCH.sub.2 Me Ph-2-Me GbPhCH.sub.2 Me PhCH.sub.2 GaPhCH.sub.2 Et Et GaPhCH.sub.2 Pr-n Pr-n GbPhCH.sub.2 (CH.sub.2).sub.4 GaPhCH.sub. 2 (CH.sub.2).sub.5 GaPh Me Me GaPh Me Et GaPh (CH.sub.2).sub.4 GaPh (CH.sub.2).sub.5 GaMe CH.sub.2CHCH.sub.2 Me GaEt CH.sub.2CHCH.sub.2 Me GaMe CH CCH.sub.2 Me GaEt CH CCH.sub.2 Me GaMe CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 GaEt CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 GaMe CH CCH.sub.2 CH CCH.sub.2 GaEt CH CCH.sub.2 CH CCH.sub.2 GaMe H H GbEt H H GbBu-i Me Me Gbcyc-Bu Me Me Gbcyc-Pen Me Me Gccyc-Hex Me Me GcPh-2-Me Me Me GbPh-3-Me Me Me GbPh-4-OMe Me Me GbPh-3-OMe Me Me GbPh-2-OMe Me Me GbPh-4-Cl Me Me GbPh-3-Cl Me Me GbPh-2-Cl Me Me GbPh-2,6-Cl.sub.2 Me Me Gb______________________________________
TABLE 2______________________________________ ##STR145##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me H Me GcMe H Et GcMe Me Me GaMe Me Et GaMe Me Pr-n GbMe Me Pr-i GbMe Me Bu-n GbMe Me Ph GaMe Me Ph-2-Cl GbMe Me Ph-2-CO.sub.2 Me GbMe Me Ph-2-OMe GbMe Me Ph-2-CF.sub.3 GbMe Me Ph-2-NO.sub.2 GbMe Me Ph-2-Me GbMe Me Ph-CH.sub.2 GaMe Et Et GaMe Pr-n Pr-n GbMe (CH.sub.2).sub.4 GaMe (CH.sub.2).sub.5 GaEt H Me GcEt H Et GcEt Me Me GaEt Me Et GaEt Me Pr-n GbEt Me Pr-i GbEt Me Bu-n GbEt Me Ph GaEt Me Ph-2-Cl GbEt Me Ph-2-CO.sub.2 Me GbEt Me Ph-2-OMe GbEt Me Ph-2-CF.sub.3 GbEt Me Ph-2-NO.sub.2 GbEt Me Ph-2-Me GbEt Me PhCH.sub.2 GaEt Et Et GaEt Pr-n Pr-n GbEt (CH.sub.2).sub.4 GaEt (CH.sub.2).sub.5 GaPr-n H Me GcPr-n H Et GcPr-n Me Me GaPr-n Me Et GaPr-n Me Ph GaPr-n Me PhCH.sub.2 GaPr-n Et Et GaPr-n Pr-n Pr-n GbPr-n (CH.sub.2).sub.4 GaPr-n (CH.sub.2).sub.5 GaCH.sub.2CHCH.sub.2 H Me GcCH.sub.2CHCH.sub.2 H Et GcCH.sub.2CHCH.sub.2 Me Me GaCH.sub.2CHCH.sub.2 Me Et GaCH.sub.2CHCH.sub.2 Me Pr-n GbCH.sub.2CHCH.sub.2 Me Pr-i GbCH.sub.2CHCH.sub.2 Me Bu-n GbCH.sub.2CHCH.sub.2 Me Ph GaCH.sub.2CHCH.sub.2 Me Ph-2-Cl GbCH.sub.2CHCH.sub.2 Me Ph-2-CO.sub.2 Me GbCH.sub.2CHCH.sub.2 Me Ph-2-OMe GbCH.sub.2CHCH.sub.2 Me Ph-2-CF.sub.3 GbCH.sub.2CHCH.sub.2 Me Ph-2-NO.sub.2 GbCH.sub.2CHCH.sub.2 Me Ph-2-Me GbCH.sub. 2CHCH.sub.2 Me PhCH.sub.2 GaCH.sub.2CHCH.sub.2 Et Et GaCH.sub.2CHCH.sub.2 Pr-n pr-n GbCH.sub.2CHCH.sub.2 (CH.sub.2).sub.4 GaCH.sub.2CHCH.sub.2 (CH.sub.2).sub.5 GaPh Me Me GaPh Me Et GaPh (CH.sub.2).sub.4 GaPh (CH.sub.2).sub.5 GaCHCCH.sub.2 Me Me GaMeOCH.sub.2 Me Me GaMeSCH.sub.2 Me Me GaMeO.sub.2 CCH.sub.2 Me Me GaPr-i Me Me GbPhCH.sub.2 Me Me Gc______________________________________
TABLE 3______________________________________ ##STR146##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________H Me Me GaMe Me Me GaEt Me Me GaPr-n Me Me GbPr-i Me Me Gbcyc-Pr Me Me Gbcyc-PrCH.sub.2 Me Me GbBu-n Me Me GbBu-sec Me Me GbBu-t Me Me GbCH.sub.2CHCH.sub.2 Me Me GaCHCCH.sub.2 Me Me GaMeOCH.sub.2 Me Me GaEtOCH.sub.2 Me Me GbMeOCH.sub.2 CH.sub.2 Me Me GaEtOCH.sub.2 CH.sub.2 Me Me GbMeOCH.sub.2 (CH.sub.3)CH Me Me GbEtOCH.sub.2 (CH.sub.3)CH Me Me GbCHF.sub.2 OCH.sub.2 Me Me GaMeSCH.sub.2 Me Me GaEtSCH.sub.2 Me Me GbMeSCH.sub.2 CH.sub.2 Me Me GaEtSCH.sub.2 CH.sub.2 Me Me GbMeSO.sub.2 CH.sub.2 Me Me GaEtSO.sub.2 CH.sub.2 Me Me GbMeSO.sub.2 CH.sub.2 CH.sub.2 Me Me GaEtSO.sub.2 CH.sub.2 CH.sub.2 Me Me GbFCH.sub.2 Me Me GaClCH.sub.2 Me Me GaBrCH.sub.2 Me Me GaICH.sub.2 Me Me GaFCH.sub.2 CH.sub.2 Me Me GaClCH.sub.2 CH.sub.2 Me Me GaBrCH.sub.2 CH.sub.2 Me Me GaICH.sub.2 CH.sub.2 Me Me GaFCH.sub.2 (CH.sub.3)CH Me Me GbClCH.sub.2 (CH.sub.3)CH Me Me GbBrCH.sub.2 (CH.sub.3)CH Me Me GbICH.sub.2 (CH.sub.3)CH Me Me GbCF.sub.3 CH.sub.2 Me Me GaNCCH.sub.2 Me Me GaNCCH.sub.2 CH.sub.2 Me Me GaMeO.sub.2 CCH.sub.2 Me Me GaEtO.sub.2 CCH.sub.2 Me Me GbPr-nO.sub.2 CCH.sub.2 Me Me GcMeO.sub.2 CCH.sub.2 CH.sub.2 Me Me GaEtO.sub.2 CCH.sub.2 CH.sub.2 Me Me GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 Me Me GcMeCOCH.sub.2 Me Me GaPhCH.sub.2 Me Me GaPh Me Me GaH Me Et GaMe Me Et GaEt Me Et GaPr-n Me Et GbPr-i Me Et Gbcyc-Pr Me Et Gbcyc-Pr CH.sub.2 Me Et GbBu-n Me Et GbBu-sec Me Et GaBu-t Me Et GaCH.sub.2CHCH.sub.2 Me Et GaCHCCH.sub.2 Me Et GbMeOCH.sub.2 Me Et GaEtOCH.sub.2 Me Et GaMeOCH.sub.2 CH.sub.2 Me Et GbEtOCH.sub.2 CH.sub.2 Me Et GbMeOCH.sub.2 (CH.sub.3)CH Me Et GbEtOCH.sub.2 (CH.sub.3)CH Me Et GbCHF.sub.2 OCH.sub.2 Me Et GbMeSCH.sub.2 Me Et GaEtSCH.sub.2 Me Et GaMeSCH.sub.2 CH.sub.2 Me Et GbEtSCH.sub.2 CH.sub.2 Me Et GaMeSO.sub.2 CH.sub.2 Me Et GbEtSO.sub.2 CH.sub.2 Me Et GaMeSO.sub.2 CH.sub.2 CH.sub.2 Me Et GbEtSO.sub.2 CH.sub.2 CH.sub.2 Me Et GbFCH.sub.2 Me Et GaClCH.sub.2 Me Et GaBrCH.sub.2 Me Et GaICH.sub.2 Me Et GaFCH.sub.2 CH.sub.2 Me Et GaClCH.sub.2 CH.sub.2 Me Et GaBrCH.sub.2 CH.sub.2 Me Et GaICH.sub.2 CH.sub.2 Me Et GaFCH.sub.2 (CH.sub.3)CH Me Et GbClCH.sub.2 (CH.sub.3)CH Me Et GbBrCH.sub.2 (CH.sub.3)CH Me Et GbICH.sub.2 (CH.sub.3)CH Me Et GbCF.sub.3 CH.sub.2 Me Et GaNCCH.sub.2 Me Et GaNCCH.sub.2 CH.sub.2 Me Et GaMeO.sub.2 CCH.sub.2 Me Et GaEtO.sub.2 CCH.sub.2 Me Et GbPr-nO.sub.2 CCH.sub.2 Me Et GcMeO.sub.2 CCH.sub.2 CH.sub.2 Me Et GaEtO.sub.2 CCH.sub.2 CH.sub.2 Me Et GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 Me Et GcMeCOCH.sub.2 Me Et GaPhCH.sub.2 Me Et GaPh Me Et GaH Me Pr-n GaMe Me Pr-n GaEt Me Pr-n GaPr-n Me Pr-n GbPr-i Me Pr-n Gbcyc-Pr Me Pr-n GbCH.sub.2CHCH.sub.2 Me Pr-n GaCHCCH.sub.2 Me Pr-n GaMeOCH.sub.2 Me Pr-n GaMeOCH.sub.2 CH.sub.2 Me Pr-n GaCHF.sub.2 OCH.sub.2 Me Pr-n GaMeSCH.sub.2 Me Pr-n GaMeSCH.sub.2 CH.sub.2 Me Pr-n GaMeSO.sub.2 CH.sub.2 Me Pr-n GaMeSO.sub.2 CH.sub.2 CH.sub.2 Me Pr-n GaFCH.sub.2 Me Pr-n GaClCH.sub.2 Me Pr-n GaBrCH.sub.2 Me Pr-n GaICH.sub.2 Me Pr-n GaFCH.sub.2 CH.sub.2 Me Pr-n GaClCH.sub.2 CH.sub.2 Me Pr-n GaBrCH.sub.2 CH.sub.2 Me Pr-n GaICH.sub.2 CH.sub.2 Me Pr-n GaCF.sub.3 CH.sub.2 Me Pr-n GaNCCH.sub.2 Me Pr-n GaNCCH.sub.2 CH.sub.2 Me Pr-n GaMeO.sub.2 CCH.sub.2 Me Pr-n GaMeCOCH.sub.2 Me Pr-n GaPhCH.sub.2 Me Pr-n GaPh Me Pr-n GaH Et Me GaMe Et Me GaEt Et Me GaPr-n Et Me GbPr-i Et Me Gbcyc-Pr Et Me Gbcyc-PrCH.sub.2 Et Me GbBu-n Et Me GbBu-sec Et Me GbBu-t Et Me GbCH.sub.2CHCH.sub.2 Et Me GaCHCCH.sub.2 Et Me GaMeOCH.sub.2 Et Me GaEtOCH.sub.2 Et Me GbMeOCH.sub.2 CH.sub.2 Et Me GaEtOCH.sub.2 CH.sub.2 Et Me GbMeOCH.sub.2 (CH.sub.3)CH Et Me GbEtOCH.sub.2 (CH.sub.3)CH Et Me GbCHF.sub.2 OCH.sub.2 Et Me GaMeSCH.sub.2 Et Me GaEtSCH.sub.2 Et Me GbMeSCH.sub.2 CH.sub.2 Et Me GaEtSCH.sub.2 CH.sub.2 Et Me GbMeSO.sub.2 CH.sub.2 Et Me GaEtSO.sub.2 CH.sub.2 Et Me GbMeSO.sub.2 CH.sub.2 CH.sub.2 Et Me GbEtSO.sub.2 CH.sub.2 CH.sub.2 Et Me GaFCH.sub.2 Et Me GaClCH.sub.2 Et Me GaBrCH.sub.2 Et Me GaICH.sub.2 Et Me GaFCH.sub.2 CH.sub.2 Et Me GaClCH.sub.2 CH.sub.2 Et Me GaBrCH.sub.2 CH.sub.2 Et Me GaICH.sub.2 CH.sub.2 Et Me GaFCH.sub.2 (CH.sub.3)CH Et Me GbClCH.sub.2 (CH.sub.3)CH Et Me GbBrCH.sub.2 (CH.sub.3)CH Et Me GbICH.sub.2 (CH.sub.3)CH Et Me GbCF.sub.3 CH.sub.2 Et Me GaNCCH.sub.2 Et Me GaNCCH.sub.2 CH.sub.2 Et Me GaMeO.sub.2 CCH.sub.2 Et Me GaEtO.sub.2 CCH.sub.2 Et Me GbPr-nO.sub.2 CCH.sub.2 Et Me GcMeO.sub.2 CCH.sub.2 CH.sub.2 Et Me GaEtO.sub.2 CCH.sub.2 CH.sub.2 Et Me GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 Et Me GcMeCOCH.sub.2 Et Me GaPhCH.sub.2 Et Me GaPh Et Me GaH Pr-n Me GaMe Pr-n Me GaEt Pr-n Me GaPr-n Pr-n Me GbPr-i Pr-n Me Gbcyc-Pr Pr-n Me GbCH.sub.2CHCH.sub.2 Pr-n Me GaCHCCH.sub.2 Pr-n Me GaMeOCH.sub.2 Pr-n Me GaMeSCH.sub.2 Pr-n Me GaMeSCH.sub.2 CH.sub.2 Pr-n Me GaMeSO.sub.2 CH.sub.2 Pr-n Me GaMeSO.sub.2 CH.sub.2 CH.sub.2 Pr-n Me GaFCH.sub.2 Pr-n Me GaClCH.sub.2 Pr-n Me GaBrCH.sub.2 Pr-n Me GaICH.sub.2 Pr-n Me GaFCH.sub.2 CH.sub.2 Pr-n Me GaClCH.sub.2 CH.sub.2 Pr-n Me GaBrCH.sub.2 CH.sub.2 Pr-n Me GaICH.sub.2 CH.sub.2 Pr-n Me GaCF.sub.3 CH.sub.2 Pr-n Me GaNCCH.sub.2 Pr-n Me GaNCCH.sub.2 CH.sub.2 Pr-n Me GaMeO.sub.2 CCH.sub.2 Pr-n Me GaMeCOCH.sub.2 Pr-n Me GaPhCH.sub.2 Pr-n Me GaPh Pr-n Me GaH Et Et GaMe Et Et GaEt Et Et GaPr-n Et Et GbPr-i Et Et Gbcyc-Pr Et Et GbCH.sub.2CHCH.sub.2 Et Et GaCHCCH.sub.2 Et Et GaMeOCH.sub.2 Et Et GaMeOCH.sub.2 CH.sub.2 Et Et GaMeSCH.sub.2 Et Et GaMeSCH.sub.2 CH.sub.2 Et Et GaMeSO.sub.2 CH.sub.2 Et Et GaMeSO.sub.2 CH.sub.2 CH.sub.2 Et Et GaFCH.sub.2 Et Et GaClCH.sub.2 Et Et GaBrCH.sub.2 Et Et GaICH.sub.2 Et Et GaFCH.sub.2 CH.sub.2 Et Et GaClCH.sub.2 CH.sub.2 Et Et GaBrCH.sub.2 CH.sub.2 Et Et GaICH.sub.2 CH.sub.2 Et Et GaCF.sub.3 CH.sub.2 Et Et GaNCCH.sub.2 Et Et GaNCCH.sub.2 CH.sub.2 Et Et GaMeO.sub.2 CCH.sub.2 Et Et GaMeO.sub.2 CCH.sub.2 CH.sub.2 Et Et GaMeCOCH.sub.2 Et Et GaPhCH.sub.2 Et Et GaPh Et Et GaH CH.sub.2CHCH.sub.2 Me GaMe CH.sub.2CHCH.sub.2 Me GaEt CH.sub.2CHCH.sub.2 Me GaPr-n CH.sub.2CHCH.sub.2 Me GbPr-i CH.sub.2CHCH.sub.2 Me Gbcyc-Pr CH.sub.2 CHCH.sub.2 Me Gbcyc-PrCH.sub.2 CH.sub.2CHCH.sub.2 Me GbBu-n CH.sub.2CHCH.sub.2 Me GbBu-sec CH.sub.2CHCH.sub.2 Me GbBu-t CH.sub.2CHCH.sub.2 Me GbCH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 Me GaCHCCH.sub.2 CH.sub.2CHCH.sub.2 Me GaMeOCH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtOCH.sub.2 CH.sub.2CHCH.sub.2 Me GbMeOCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtOCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GbMeOCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Me GbEtOCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Me GbCHF.sub.2 OCH.sub.2 CH.sub.2CHCH.sub.2 Me GaMeSCH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtSCH.sub.2 CH.sub.2CHCH.sub.2 Me GbMeSCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtSCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GbMeSO.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtSO.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GbMeSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtSO.sub.2 CH.sub. 2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GbFCH.sub.2 CH.sub.2CHCH.sub.2 Me GaClCH.sub.2 CH.sub.2CHCH.sub.2 Me GaBrCH.sub.2 CH.sub.2CHCH.sub.2 Me GaICH.sub.2 CH.sub.2CHCH.sub.2 Me GaFCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaClCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaBrCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaICH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaFCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Me GbClCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Me GbBrCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Me GbICH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Me GbCF.sub.3 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaNCCH.sub.2 CH.sub.2CHCH.sub.2 Me GaNCCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaMeO.sub.2 CCH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtO.sub.2 CCH.sub.2 CH.sub.2CHCH.sub.2 Me GbPr-nO.sub.2 CCH.sub.2 CH.sub.2CHCH.sub.2 Me GcMeO.sub.2 CCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GaEtO.sub.2 CCH.sub.2 CH.sub. 2 CH.sub.2CHCH.sub.2 Me GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Me GcMeCOCH.sub.2 CH.sub.2CHCH.sub.2 Me GaPhCH.sub.2 CH.sub.2CHCH.sub.2 Me GaPh CH.sub.2CHCH.sub.2 Me GaH CH.sub.2CHCH.sub.2 Et GaMe CH.sub.2CHCH.sub.2 Et GaEt CH.sub.2CHCH.sub.2 Et GaPr-n CH.sub.2CHCH.sub.2 Et GbPr-i CH.sub.2CHCH.sub.2 Et Gbcyc-Pr CH.sub.2CHCH.sub.2 Et Gbcyc-PrCH.sub.2 CH.sub.2CHCH.sub.2 Et GbBu-n CH.sub.2CHCH.sub.2 Et GbBu-sec CH.sub.2CHCH.sub.2 Et GbBu-t CH.sub.2CHCH.sub.2 Et GbCH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 Et GaCHCCH.sub.2 CH.sub.2CHCH.sub.2 Et GaMeOCH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtOCH.sub.2 CH.sub.2CHCH.sub.2 Et GbMeOCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtOCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GbMeOCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Et GbEtOCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Et GbCHF.sub.2 OCH.sub.2 CH.sub.2CHCH.sub.2 Et GaMeSCH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtSCH.sub.2 CH.sub.2CHCH.sub.2 Et GbMeSCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtSCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GbMeSO.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtSO.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GbMeSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GbFCH.sub.2 CH.sub.2CHCH.sub.2 Et GaClCH.sub.2 CH.sub.2CHCH.sub.2 Et GaBrCH.sub.2 CH.sub.2CHCH.sub.2 Et GaICH.sub.2 CH.sub.2CHCH.sub.2 Et GaFCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaClCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaBrCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaICH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaFCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Et GbClCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Et GbBrCH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Et GbICH.sub.2 (CH.sub.3)CH CH.sub.2CHCH.sub.2 Et GbCF.sub.3 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaNCCH.sub.2 CH.sub.2CHCH.sub.2 Et GaNCCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaMeO.sub.2 CCH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtO.sub.2 CCH.sub.2 CH.sub.2CHCH.sub.2 Et GbPr-nO.sub.2 CCH.sub.2 CH.sub.2CHCH.sub.2 Et GcMeO.sub.2 CCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GaEtO.sub.2 CCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 CH.sub.2CHCH.sub.2 Et GcMeCOCH.sub.2 CH.sub.2CHCH.sub.2 Et GaPhCH.sub.2 CH.sub.2CHCH.sub.2 Et GaPh CH.sub.2CHCH.sub.2 Et GaH Ph Me GaMe Ph Me GaEt Ph Me GaPr-n Ph Me GbPr-i Ph Me Gbcyc-Pr Ph Me Gbcyc-PrCH.sub.2 Ph Me GbBu-n Ph Me GbBu-sec Ph Me GbBu-t Ph Me GbCH.sub.2CHCH.sub.2 Ph Me GaCHCCH.sub.2 Ph Me GaMeOCH.sub.2 Ph Me GaEtOCH.sub.2 Ph Me GbMeOCH.sub.2 CH.sub. 2 Ph Me GaEtOCH.sub.2 CH.sub.2 Ph Me GbMeOCH.sub.2 (CH.sub.3)CH Ph Me GbEtOCH.sub.2 (CH.sub.3)CH Ph Me GbCHF.sub.2 OCH.sub.2 Ph Me GaMeSCH.sub.2 Ph Me GaEtSCH.sub.2 Ph Me GbMeSCH.sub.2 CH.sub.2 Ph Me GaEtSCH.sub.2 CH.sub.2 Ph Me GbMeSO.sub.2 CH.sub.2 Ph Me GaEtSO.sub.2 CH.sub.2 Ph Me GbMeSO.sub.2 CH.sub.2 CH.sub.2 Ph Me GbEtSO.sub.2 CH.sub.2 CH.sub.2 Ph Me GaFCH.sub.2 Ph Me GaClCH.sub.2 Ph Me GaBrCH.sub.2 Ph Me GaICH.sub.2 Ph Me GaFCH.sub.2 CH.sub.2 Ph Me GaClCH.sub.2 CH.sub.2 Ph Me GaBrCH.sub.2 CH.sub.2 Ph Me GaICH.sub.2 CH.sub.2 Ph Me GaFCH.sub.2 (CH.sub.3)CH Ph Me GbClCH.sub.2 (CH.sub.3)CH Ph Me GbBrCH.sub.2 (CH.sub.3)CH Ph Me GbICH.sub.2 (CH.sub.3)CH Ph Me GbCF.sub.3 CH.sub.2 Ph Me GaNCCH.sub.2 Ph Me GaNCCH.sub.2 CH.sub.2 Ph Me GaMeO.sub.2 CCH.sub.2 Ph Me GaEtO.sub.2 CCH.sub.2 Ph Me GbPr-nO.sub.2 CCH.sub.2 Ph Me GcMeO.sub.2 CCH.sub.2 CH.sub.2 Ph Me GaEtO.sub.2 CCH.sub.2 CH.sub.2 Ph Me GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 Ph Me GcMeCOCH.sub.2 Ph Me GaPhCH.sub.2 Ph Me GaPh Ph Me GaH Ph Et GaMe Ph Et GaEt Ph Et GaPr-n Ph Et GbPr-i Ph Et Gbcyc-Pr Ph Et Gbcyc-PrCH.sub.2 Ph Et GbBu-n Ph Et GbBu-sec Ph Et GbBu-t Ph Et GbCH.sub.2CHCH.sub.2 Ph Et GaCHCCH.sub.2 Ph Et GaMeOCH.sub.2 Ph Et GaEtOCH.sub.2 Ph Et GbMeOCH.sub.2 CH.sub.2 Ph Et GaEtOCH.sub.2 CH.sub.2 Ph Et GbMeOCH.sub.2 (CH.sub.3)CH Ph Et GbEtOCH.sub.2 (CH.sub.3)CH Ph Et GbCHF.sub.2 OCH.sub.2 Ph Et GaMeSCH.sub.2 Ph Et GaEtSCH.sub.2 Ph Et GbMeSCH.sub.2 CH.sub.2 Ph Et GaEtSCH.sub.2 CH.sub.2 Ph Et GbMeSO.sub.2 CH.sub.2 Ph Et GaEtSO.sub.2 CH.sub.2 Ph Et GbMeSO.sub.2 CH.sub.2 CH.sub.2 Ph Et GaEtSO.sub.2 CH.sub.2 CH.sub.2 Ph Et GbFCH.sub.2 Ph Et GaClCH.sub.2 Ph Et GaBrCH.sub.2 Ph Et GaICH.sub.2 Ph Et GaFCH.sub.2 CH.sub.2 Ph Et GaClCH.sub.2 CH.sub.2 Ph Et GaBrCH.sub.2 CH.sub.2 Ph Et GaICH.sub.2 CH.sub.2 Ph Et GaFCH.sub.2 (CH.sub.3)CH Ph Et GbClCH.sub.2 (CH.sub.3)CH Ph Et GbBrCH.sub.2 (CH.sub.3)CH Ph Et GbICH.sub.2 (CH.sub.3)CH Ph Et GbCF.sub.3 CF.sub.2 Ph Et GaNCCH.sub.2 Ph Et GaNCCH.sub.2 CH.sub.2 Ph Et GaMeO.sub.2 CCH.sub.2 Ph Et GaEtO.sub.2 CCH.sub.2 Ph Et GbPr-nO.sub.2 CCH.sub.2 Ph Et GcMeO.sub.2 CCH.sub.2 CH.sub.2 Ph Et GaEtO.sub.2 CCH.sub.2 CH.sub.2 Ph Et GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 Ph Et GcMeCOCH.sub.2 Ph Et GaPhCH.sub.2 Ph Et GaPh Ph Et GaH (CH.sub.2).sub.3 GaMe (CH.sub.2).sub.3 GaEt (CH.sub.2).sub.3 GaPr-n (CH.sub.2).sub.3 GbPr-i (CH.sub.2).sub.3 Gbcyc-Pr (CH.sub.2).sub.3 Gbcyc-PrCH.sub.2 (CH.sub.2).sub.3 GbBu-n (CH.sub.2).sub.3 GbBu-sec (CH.sub.2).sub.3 GbBu-t (CH.sub.2).sub.3 GbCH.sub.2CHCH.sub.2 (CH.sub.2).sub.3 GaCHCCH.sub.2 (CH.sub.2).sub.3 GaMeOCH.sub.2 (CH.sub.2).sub.3 GaEtOCH.sub.2 (CH.sub.2).sub.3 GbMeOCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaEtOCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GbMeOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.3 GbEtOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.3 GbCHF.sub.2 OCH.sub.2 (CH.sub.2).sub.3 GaMeSCH.sub.2 (CH.sub.2).sub.3 GaEtSCH.sub.2 (CH.sub.2).sub.3 GbMeSCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaEtSCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GbMeSO.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaEtSO.sub.2 CH.sub.2 (CH.sub.2).sub.3 GbMeSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GbEtSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaFCH.sub.2 (CH.sub.2).sub.3 GaClCH.sub.2 (CH.sub.2).sub.3 GaBrCH.sub.2 (CH.sub.2).sub.3 GaICH.sub.2 (CH.sub.2).sub.3 GaFCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaClCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaBrCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaICH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaFCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.3 GbClCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.3 GbBrCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.3 GbICH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.3 GbCF.sub.3 CH.sub.2 (CH.sub.2).sub.3 GaNCCH.sub.2 (CH.sub. 2).sub.3 GaNCCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaMeO.sub.2 CCH.sub.2 (CH.sub.2).sub.3 GaEtO.sub.2 CCH.sub.2 (CH.sub.2).sub.3 GbPr-nO.sub.2 CCH.sub.2 (CH.sub.2).sub.3 GcMeO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GaEtO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.3 GcMeCOCH.sub.2 (CH.sub.2).sub.3 GaPhCH.sub.2 (CH.sub.2).sub.3 GaPh (CH.sub.2).sub.3 GaH (CH.sub.2).sub.4 GaMe (CH.sub.2).sub.4 GaEt (CH.sub.2).sub.4 GaPr-n (CH.sub.2).sub.4 GbPr-i (CH.sub.2).sub.4 Gbcyc-Pr (CH.sub.2).sub.4 Gbcyc-PrCH.sub.2 (CH.sub.2).sub.4 GbBu-n (CH.sub.2).sub.4 GbBu-sec (CH.sub.2).sub.4 GbBu-t (CH.sub.2).sub.4 GbCH.sub.2CHCH.sub.2 (CH.sub.2).sub.4 GaCHCCH.sub.2 (CH.sub.2).sub.4 GaMeOCH.sub.2 (CH.sub.2).sub.4 GaEtOCH.sub.2 (CH.sub.2).sub.4 GbMeOCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtOCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GbMeOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GbEtOCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GbCHF.sub.2 OCH.sub.2 (CH.sub.2).sub.4 GaMeSCH.sub.2 (CH.sub.2).sub.4 GaEtSCH.sub.2 (CH.sub.2).sub.4 GbMeSCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtSCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GbMeSO.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtSO.sub.2 CH.sub.2 (CH.sub.2).sub.4 GbMeSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtSO.sub.2 CH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GbFCH.sub.2 (CH.sub.2).sub.4 GaClCH.sub.2 (CH.sub.2).sub.4 GaBrCH.sub.2 (CH.sub.2).sub.4 GaICH.sub.2 (CH.sub.2).sub.4 GaFCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaClCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaBrCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaICH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaFCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GbClCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GbBrCH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GbICH.sub.2 (CH.sub.3)CH (CH.sub.2).sub.4 GbCF.sub.3 CH.sub.2 (CH.sub.2).sub.4 GaNCCH.sub.2 (CH.sub.2).sub.4 GaNCCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaMeO.sub.2 CCH.sub.2 (CH.sub.2).sub.4 GaEtO.sub.2 CCH.sub.2 (CH.sub.2).sub.4 GbPr-nO.sub.2 CCH.sub.2 (CH.sub.2).sub.4 GcMeO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GaEtO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GbPr-nO.sub.2 CCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GcMeCOCH.sub.2 (CH.sub.2).sub.4 GaPhCH.sub.2 (CH.sub.2).sub.4 GaPh (CH.sub.2).sub.4 Ga______________________________________
TABLE 4______________________________________ ##STR147##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me GbMe Me Et GcMe Et Et GbMe Me Ph GcMe (CH.sub.2).sub.4 GbMe (CH.sub.2).sub.5 GbEt Me Me GbEt Me Et GcEt Et Et GbEt Me Ph GcEt (CH.sub.2).sub.4 GbEt (CH.sub.2).sub.5 GbPr-n Me Me GbPr-n Me Et GcPr-n Et Et GbPr-n Me Ph GcPr-n (CH.sub.2).sub.4 GbPr-n (CH.sub.2).sub.5 GbCH.sub.2CHCH.sub.2 Me Me GbCH.sub.2CHCH.sub.2 Me Et GcCH.sub.2CHCH.sub.2 Et Et GbCH.sub.2CHCH.sub.2 Me Ph GcCH.sub.2CHCH.sub.2 (CH.sub.2 ).sub.4 GbCH.sub.2CHCH.sub.2 (CH.sub.2).sub.5 GbCHCCH.sub.2 Me Me GbCHCCH.sub.2 Me Et GcCHCCH.sub.2 Et Et GbCHCCH.sub.2 Me Ph GcCHCCH.sub.2 (CH.sub.2).sub.4 GbCHCCH.sub.2 (CH.sub.2).sub.5 GbMeOCH.sub.2 CH.sub.2 Me Me GbMeOCH.sub.2 CH.sub.2 Me Et GcMeOCH.sub.2 CH.sub.2 Et Et GbMeOCH.sub.2 CH.sub.2 Me Ph GcMeOCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GbMeOCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GbClCH.sub.2 CH.sub.2 Me Me GbClCH.sub.2 CH.sub.2 Me Et GcClCH.sub.2 CH.sub.2 Et Et GbClCH.sub.2 CH.sub.2 Me Ph GcClCH.sub.2 CH.sub.2 (CH.sub.2).sub.4 GbClCH.sub.2 CH.sub.2 (CH.sub.2).sub.5 GbCF.sub.3 CH.sub.2 Me Me GbCF.sub.3 CH.sub.2 Me Et GcCF.sub.3 CH.sub.2 Et Et GbCF.sub.3 CH.sub.2 Me Ph GcCF.sub.3 CH.sub.2 (CH.sub.2).sub.4 GbCF.sub.3 CH.sub.2 (CH.sub.2).sub.5 GbNCCH.sub.2 Me Me GbNCCH.sub.2 Me Et GcNCCH.sub.2 Et Et GbNCCH.sub.2 Me Ph GcNCCH.sub.2 (CH.sub.2).sub.4 GbNCCH.sub.2 (CH.sub.2).sub.5 GbMeO.sub.2 CCH.sub.2 Me Me GbMeO.sub.2 CCH.sub.2 Me Et GcMeO.sub.2 CCH.sub.2 Et Et GbMeO.sub.2 CCH.sub.2 Me Ph GcMeO.sub.2 CCH.sub.2 (CH.sub.2).sub.4 GbMeO.sub.2 CCH.sub.2 (CH.sub.2).sub.5 GbPhCH.sub.2 Me Me GbPhCH.sub.2 Me Et GcPhCH.sub.2 Et Et GbPhCH.sub.2 Me Ph GcPhCH.sub.2 (CH.sub.2).sub.4 GbPhCH.sub.2 (CH.sub.2).sub.5 Gb______________________________________
TABLE 5______________________________________ ##STR148##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me GbMe Me Et GcMe Et Et GbMe Me Ph GcMe (CH.sub.2).sub.4 GbMe (CH.sub.2).sub.5 GbEt Me Me GbEt Me Et GcEt Et Et GbEt Me Ph GcEt (CH.sub.2).sub.4 GbEt (CH.sub.2).sub.5 GbPr-n Me Me GbPr-n Me Et GcPr-n Et Et GbPr-n Me Ph GcPr-n (CH.sub.2).sub.4 GbPr-n (CH.sub.2).sub.5 GbCH.sub.2CHCH.sub.2 Me Me GbCH.sub.2CHCH.sub.2 Me Et GcCH.sub.2CHCH.sub.2 Et Et GbCH.sub.2CHCH.sub.2 Me Ph GcCH.sub.2CHCH.sub.2 (CH.sub. 2).sub.4 GbCH.sub.2CHCH.sub.2 (CH.sub.2).sub.5 Gb______________________________________
TABLE 6______________________________________ ##STR149##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me GbEt Me Me Gbcyc-Pr Me Me GbCH.sub.2CHCH.sub.2 Me Me GcCHCCH.sub.2 Me Me GcMeOCH.sub.2 Me Me GcMeOCH.sub.2 CH.sub.2 Me Me GcMeSCH.sub.2 Me Me GcMeSO.sub.2 CH.sub.2 Me Me GcClCH.sub.2 CH.sub.2 Me Me GcCF.sub.3 CH.sub.2 Me Me GcNCCH.sub.2 CH.sub.2 Me Me GcMeO.sub.2 CCH.sub.2 Me Me GcMeCOCH.sub.2 Me Me GcPhCH.sub.2 Me Me GcPh Me Me GcMe Me Et GbMe Me Pr-n GbMe Et Me GbMe Pr-n Me GbMe Et Et GbMe CH.sub.2CHCH.sub.2 Me GbMe CH.sub.2CHCH.sub.2 Et GbMe Ph Me GbMe Ph Et GbMe (CH.sub.2).sub.3 GbMe (CH.sub.2).sub.4 Gb______________________________________
TABLE 7______________________________________ ##STR150##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________H H H H GaH H H Me GaH H H Et GbH Me H H GaH Et H H GbH Me H Me GbH Me H Et GbH H Me Me GaH H Me Et GbH H H CF.sub.3 GaH H H CH.sub.2 F GaH H H CH.sub.2 Cl GaH H H CH.sub.2 Br GbH H H CH.sub.2 I GbH H H CH.sub.2 OMe GaH H H CH.sub.2 OEt GaH H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaH H H CH.sub.2 OCH.sub.2 CCH GaH H H CH.sub.2 OCHF.sub. 2 GaH H H CH.sub.2 OCF.sub.3 GaH H H CH.sub.2 SMe GaH H H CH.sub.2 SEt GaH H H CH.sub.2 SO.sub.2 Me GaH H H CH.sub.2 SO.sub.2 Et GaH H H CH.sub.2 CF.sub.3 GaH H H CH.sub.2 CN GaH H H CO.sub.2 Me GaH H H CO.sub.2 Et GaH H H CH.sub.2 CO.sub.2 Me GaH H H CH.sub.2 CO.sub.2 Et GaH H H COMe GaH H H COEt GaH H H CH.sub.2 COMe GaH H H CH.sub.2 COEt GaMe H H H GaMe H H Me GaMe H H Et GbMe H H Pr-n GbMe H H Pr-i GbMe H H Bu-n GcMe Me H H GaMe Et H H GbMe Me H Me GbMe Me H Et GbMe H Me Me GaMe H Me Et GbMe H H F GaMe H H Cl GaMe H H Br GbMe H H I GbMe H H CF.sub.3 GaMe H H CH.sub.2 F GaMe H H CH.sub.2 Cl GaMe H H CH.sub.2 Br GbMe H H CH.sub.2 I GbMe H H CH.sub.2 CH.sub.2 F GaMe H H CH.sub.2 CH.sub.2 Cl GaMe H H CH.sub.2 CH.sub.2 Br GbMe H H CH.sub.2 CH.sub.2 I GbMe H H CH(CH.sub.3)CH.sub.2 F GaMe H H CH(CH.sub.3)CH.sub.2 Cl GaMe H H CH(CH.sub.3)CH.sub.2 Br GbMe H H CH(CH.sub.3 CH.sub.2 I GbMe H H CH.sub.2 OMe GaMe H H CH.sub.2 OEt GaMe H H CH.sub.2 CH.sub.2 OMe GaMe H H CH.sub.2 CH.sub.2 OEt GaMe H H CH(CH.sub.3)CH.sub.2 OMe GbMe H H CH(CH.sub.3)CH.sub.2 OEt GbMe H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaMe H H CH.sub.2 OCH.sub.2 CCH GaMe H H CH.sub.2 OCHF.sub.2 GaMe H H CH.sub.2 OCF.sub.3 GaMe H H CH.sub. 2 SMe GaMe H H CH.sub.2 SEt GaMe H H CH.sub.2 SO.sub.2 Me GaMe H H CH.sub.2 SO.sub.2 Et GaMe H H CH.sub.2 CF.sub.3 GaMe H H CH.sub.2 CN GaMe H H CO.sub.2 Me GaMe H H CO.sub.2 Et GaMe H H CO.sub.2 Pr-n GbMe H H CH.sub.2 CO.sub.2 Me GaMe H H CH.sub.2 CO.sub.2 Et GaMe H H CH.sub.2 CO.sub.2 Pr-n GbMe H H COMe GaMe H H COEt GaMe H H COPr-n GbMe H H CH.sub.2 COMe GaMe H H CH.sub.2 COEt GaEt H H H GaEt H H Me GaEt H H Et GbEt H H Pr-n GbEt H H Pr-i GbEt H H Bu-n GcEt Me H H GaEt Et H H GbEt Me H Me GbEt Me H Et GbEt H Me Me GaEt H Me Et GbEt H H F GaEt H H Cl GaEt H H Br GbEt H H I GbEt H H CF.sub.3 GaEt H H CH.sub.2 F GaEt H H CH.sub.2 Cl GaEt H H CH.sub.2 Br GbEt H H CH.sub.2 I GbEt H H CH.sub.2 CH.sub.2 F GaEt H H CH.sub.2 CH.sub.2 Cl GaEt H H CH.sub.2 CH.sub.2 Br GbEt H H CH.sub.2 CH.sub.2 I GbEt H H CH(CH.sub.3)CH.sub.2 F GaEt H H CH(CH.sub.3)CH.sub.2 Cl GaEt H H CH(CH.sub.3)CH.sub.2 Br GbEt H H CH(CH.sub.3)CH.sub.2 I GbEt H H CH.sub.2 OMe GaEt H H CH.sub.2 OEt GaEt H H CH.sub.2 CH.sub.2 OMe GaEt H H CH.sub.2 CH.sub.2 OEt GaEt H H CH(CH.sub.3)CH.sub.2 OMe GbEt H H CH(CH.sub.3)CH.sub.2 OEt GbEt H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaEt H H CH.sub.2 OCH.sub.2 CCH GaEt H H CH.sub.2 OCHF.sub.2 GaEt H H CH.sub.2 OCF.sub.3 GaEt H H CH.sub.2 SMe GaEt H H CH.sub.2 SEt GaEt H H CH.sub.2 SO.sub.2 Me GaEt H H CH.sub.2 SO.sub.2 Et GaEt H H CH.sub.2 CF.sub.3 GaEt H H CH.sub.2 CN GaEt H H CO.sub.2 Me GaEt H H CO.sub.2 Et GaEt H H CO.sub.2 Pr-n GbEt H H CH.sub.2 CO.sub.2 Me GaEt H H CH.sub.2 CO.sub.2 Et GaEt H H CH.sub.2 CO.sub.2 Pr-n GbEt H H COMe GaEt H H COEt GaEt H H COPr-n GbEt H H CH.sub.2 COMe GaEt H H CH.sub.2 COEt GaPr-n H H H GaPr-n H H Me GaPr-n H H Et GbPr-n Me H H GaPr-n Et H H GbPr-n Me H Me GbPr-n Me H Et GbPr-n H Me Me GaPr-n H Me Et GbPr-n H H CF.sub.3 GaPr-n H H CH.sub.2 F GaPr-n H H CH.sub.2 Cl GaPr-n H H CH.sub.2 Br GbPr-n H H CH.sub.2 I GbPr-n H H CH.sub.2 OMe GaPr-n H H CH.sub.2 OEt GaPr-n H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaPr-n H H CH.sub.2 OCH.sub.2 CCH GaPr-n H H CH.sub.2 OCHF.sub.2 GaPr-n H H CH.sub.2 OCF.sub.3 GaPr-n H H CH.sub.2 SMe GaPr-n H H CH.sub.2 SEt GaPr-n H H CH.sub.2 SO.sub.2 Me GaPr-n H H CH.sub.2 SO.sub.2 Et GaPr-n H H CH.sub.2 CF.sub.3 GaPr-n H H CH.sub.2 CN GaPr-n H H CO.sub.2 Me GaPr-n H H CO.sub.2 Et GaPr-n H H CH.sub.2 CO.sub.2 Me GaPr-n H H CH.sub.2 CO.sub.2 Et GaPr-n H H COMe GaPr-n H H COEt GaPr-n H H CH.sub.2 COMe GaPr-n H H CH.sub.2 COEt GaPr-i H H H GaPr-i H H Me GaPr-i H H Et GbPr-i Me H H GaPr-i Et H H GbPr-i Me H Me GbPr-i Me H Et GbPr-i H Me Me GaPr-i H Me Et GbPr-i H H CF.sub.3 GaPr-i H H CH.sub.2 F GaPr-i H H CH.sub.2 Cl GaPr-i H H CH.sub.2 Br GbPr-i H H CH.sub.2 I GbPr-i H H CH.sub.2 OMe GaPr-i H H CH.sub.2 OEt GaPr-i H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaPr-i H H CH.sub.2 OCH.sub.2 CCH GaPr-i H H CH.sub.2 OCHF.sub.2 GaPr-i H H CH.sub.2 OCF.sub.3 GaPr-i H H CH.sub.2 SMe GaPr-i H H CH.sub.2 SEt GaPr-i H H CH.sub.2 SO.sub.2 Me GaPr-i H H CH.sub.2 SO.sub.2 Et GaPr-i H H CH.sub.2 CF.sub.3 GaPr-i H H CH.sub.2 CN GaPr-i H H CO.sub.2 Me GaPr-i H H CO.sub.2 Et GaPr-i H H CH.sub.2 CO.sub.2 Me GaPr-i H H CH.sub.2 CO.sub.2 Et GaPr-i H H COMe GaPr-i H H COEt GaPr-i H H CH.sub.2 COMe GaPr-i H H CH.sub.2 COEt GaBu-n H H H GaBu-n H H Me GaBu-n Me H H GaBu-n Me H Me GbBu-n H Me Me GaBu-n H H CF.sub.3 GaBu-n H H CH.sub.2 F GaBu-n H H CH.sub.2 Cl GaBu-n H H CH.sub.2 Br GbBu-n H H CH.sub.2 I GbBu-n H H CH.sub.2 OMe GaBu-n H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaBu-n H H CH.sub.2 OCH.sub.2 CCH GaBu-n H H CH.sub.2 OCHF.sub.2 GaBu-n H H CH.sub.2 OCF.sub.3 GaBu-n H H CH.sub.2 SMe GaBu-n H H CH.sub.2 SO.sub.2 Me GaBu-n H H CH.sub.2 CF.sub.3 GaBu-n H H CH.sub.2 CN GaBu-n H H CO.sub.2 Me GaBu-n H H CH.sub.2 CO.sub.2 Me GaBu-n H H COMe GaBu-n H H CH.sub.2 COMe GaCH.sub.2 CHCH.sub.2 H H H GaCH.sub.2 CHCH.sub.2 H H Me GbCH.sub.2 CHCH.sub.2 H H Et GbCH.sub.2 CHCH.sub.2 Me H H GaCH.sub.2 CHCH.sub.2 Et H H GbCH.sub.2 CHCH.sub.2 Me H Me GbCH.sub.2 CHCH.sub.2 Me H Et GbCH.sub.2 CHCH.sub.2 H Me Me GaCH.sub.2 CHCH.sub.2 H Me Et GbCH.sub.2 CHCH.sub.2 H H CF.sub.3 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 F GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 Cl GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 Br GbCH.sub.2 CHCH.sub.2 H H CH.sub.2 I GbCH.sub.2 CHCH.sub.2 H H CH.sub.2 OMe GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OEt GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OCHF.sub.2 GaCH.sub. 2 CHCH.sub.2 H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SMe GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SEt GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CF.sub.3 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CN GaCH.sub.2 CHCH.sub.2 H H CO.sub.2 Me GaCH.sub.2 CHCH.sub.2 H H CO.sub.2 Et GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CHCH.sub.2 H H COMe GaCH.sub.2 CHCH.sub.2 H H COEt GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 COMe GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 COEt GaCH.sub.2 CCH H H H GaCH.sub.2 CCH H H Me GbCH.sub.2 CCH H H Et GbCH.sub.2 CCH Me H H GaCH.sub.2 CCH Et H H GbCH.sub.2 CCH Me H Me GbCH.sub.2 CCH Me H Et GbCH.sub.2 CCH H Me Me GaCH.sub.2 CCH H H F GaCH.sub.2 CCH H Me Et GbCH.sub.2 CCH H H CF.sub.3 GaCH.sub.2 CCH H H CH.sub.2 F GaCH.sub.2 CCH H H CH.sub.2 Cl GaCH.sub.2 C CH H H CH.sub.2 Br GbCH.sub.2 CCH H H CH.sub.2 I GbCH.sub.2 CCH H H CH.sub.2 OMe GaCH.sub.2 CCH H H CH.sub.2 OEt GaCH.sub.2 CCH H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CCH H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CCH H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CCH H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CCH H H CH.sub.2 SMe GaCH.sub.2 CCH H H CH.sub.2 SEt GaCH.sub.2 CCH H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CCH H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CCH H H CH.sub.2 CF.sub.3 GaCH.sub.2 CCH H H CH.sub.2 CN GaCH.sub.2 CCH H H CO.sub.2 Me GaCH.sub.2 CCH H H CO.sub.2 Et GaCH.sub.2 CCH H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CCH H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CCH H H COMe GaCH.sub.2 CCH H H COEt GaCH.sub. 2 CCH H H CH.sub.2 COMe GaCH.sub.2 CCH H H CH.sub.2 COEt GaCH.sub.2 OMe H H H GaCH.sub.2 OMe H H Me GbCH.sub.2 OMe H H Et GbCH.sub.2 OMe H H Pr-n GbCH.sub.2 OMe H H Pr-i GbCH.sub.2 OMe H H Bu-n GcCH.sub.2 OMe Me H H GaCH.sub.2 OMe Et H H GbCH.sub.2 OMe Me H Me GbCH.sub.2 OMe Me H Et GbCH.sub.2 OMe H Me Me GaCH.sub.2 OMe H Me Et GbCH.sub.2 OMe H H F GaCH.sub.2 OMe H H Cl GaCH.sub.2 OMe H H Br GbCH.sub.2 OMe H H I GbCH.sub.2 OMe H H CF.sub.3 GaCH.sub.2 OMe H H CH.sub.2 F GaCH.sub.2 OMe H H CH.sub.2 Cl GaCH.sub.2 OMe H H CH.sub.2 Br GbCH.sub.2 OMe H H CH.sub.2 I GbCH.sub.2 OMe H H CH.sub.2 CH.sub.2 F GaCH.sub.2 OMe H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 OMe H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 OMe H H CH.sub.2 CH.sub.2 I GbCH.sub.2 OMe H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 OMe H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 OMe H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 OMe H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 OMe H H CH.sub.2 OMe GaCH.sub.2 OMe H H CH.sub.2 OEt GaCH.sub.2 OMe H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 OMe H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 OMe H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 OMe H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 OMe H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 OMe H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 OMe H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 OMe H H CH.sub.2 OCF.sub.3 GaCH.sub.2 OMe H H CH.sub.2 SMe GaCH.sub.2 OMe H H CH.sub.2 SEt GaCH.sub.2 OMe H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 OMe H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 OMe H H CH.sub.2 CF.sub.3 GaCH.sub.2 OMe H H CH.sub.2 CN GaCH.sub.2 OMe H H CO.sub.2 Me GaCH.sub.2 OMe H H CO.sub.2 Et GaCH.sub.2 OMe H H CO.sub.2 Pr-n GbCH.sub.2 OMe H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 OMe H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 OMe H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 OMe H H COMe GaCH.sub.2 OMe H H COEt GaCH.sub.2 OMe H H COPr-n GbCH.sub.2 OMe H H CH.sub.2 COMe GaCH.sub.2 OMe H H CH.sub.2 COEt GaCH.sub.2 OEt H H H GaCH.sub.2 OEt H H Me GbCH.sub.2 OEt H H Et GbCH.sub.2 OEt Me H H GaCH.sub.2 OEt Et H H GbCH.sub.2 OEt Me H Me GbCH.sub.2 OEt Me H Et GbCH.sub.2 OEt H Me Me GaCH.sub.2 OEt H Me Et GbCH.sub.2 OEt H H CF.sub.3 GaCH.sub.2 OEt H H CH.sub.2 F GaCH.sub.2 OEt H H CH.sub.2 Cl GaCH.sub.2 OEt H H CH.sub.2 Br GbCH.sub.2 OEt H H CH.sub.2 I GbCH.sub.2 OEt H H CH.sub.2 OMe GaCH.sub.2 OEt H H CH.sub.2 OEt GaCH.sub.2 OEt H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 OEt H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 OEt H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 OEt H H CH.sub.2 OCF.sub.3 GaCH.sub.2 OEt H H CH.sub.2 SMe GaCH.sub.2 OEt H H CH.sub.2 SEt GaCH.sub.2 OEt H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 OEt H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 OEt H H CH.sub.2 CF.sub.3 GaCH.sub.2 OEt H H CH.sub.2 CN GaCH.sub.2 OEt H H CO.sub.2 Me GaCH.sub.2 OEt H H CO.sub.2 Et GaCH.sub.2 OEt H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 OEt H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 OEt H H COMe GaCH.sub.2 OEt H H COEt GaCH.sub.2 OEt H H CH.sub.2 COMe GaCH.sub.2 OEt H H CH.sub.2 COEt GaCH.sub.2 CH.sub.2 OMe H H H GaCH.sub.2 CH.sub.2 OMe H H Me GbCH.sub.2 CH.sub.2 OMe H H Et GbCH.sub.2 CH.sub.2 OMe Me H H GaCH.sub.2 CH.sub.2 OMe Et H H GbCH.sub.2 CH.sub.2 OMe Me H Me GbCH.sub.2 CH.sub.2 OMe Me H Et GbCH.sub.2 CH.sub.2 OMe H Me Me GaCH.sub.2 CH.sub.2 OMe H Me Et GbCH.sub.2 CH.sub.2 OMe H H CF.sub.3 GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 F GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 Cl GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 Cl GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 OMe H H CH.sub.2 I GbCH.sub.2 CH.sub.2 OMe H H CH.sub.2 OMe GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 OEt GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 SMe GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 SEt GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 CF.sub.3 GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 CN GaCH.sub.2 CH.sub.2 OMe H H CO.sub.2 Me GaCH.sub.2 CH.sub.2 OMe H H CO.sub.2 Et GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CH.sub.2 OMe H H COMe GaCH.sub.2 CH.sub.2 OMe H H COEt GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 COMe GaCH.sub.2 CH.sub.2 OMe H H CH.sub.2 COEt GaCH.sub.2 CH.sub.2 OEt H H H GaCH.sub.2 CH.sub.2 OEt H H Me GbCH.sub.2 CH.sub.2 OEt Me H H GaCH.sub.2 CH.sub.2 OEt Me H Me GbCH.sub.2 CH.sub.2 OEt H Me Me GaCH.sub.2 CH.sub.2 OEt H H CF.sub.3 GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 F GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 Cl GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 OEt H H CH.sub.2 I GbCH.sub.2 CH.sub.2 OEt H H CH.sub.2 OMe GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 OCH.sub.2 C CH GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 SMe GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 CF.sub.3 GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 CN GaCH.sub.2 CH.sub.2 OEt H H CO.sub.2 Me GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CH.sub.2 OEt H H COMe GaCH.sub.2 CH.sub.2 OEt H H CH.sub.2 COMe GaCH(CH.sub.3)CH.sub.2 OMe H H H GaCH(CH.sub.3)CH.sub.2 OMe H H Me GbCH(CH.sub.3)CH.sub.2 OMe H H Et GbCH(CH.sub.3)CH.sub.2 OMe Me H H GaCH(CH.sub.3)CH.sub.2 OMe Et H H GbCH(CH.sub.3)CH.sub.2 OMe Me H Me GbCH(CH.sub.3)CH.sub.2 OMe Me H Et GbCH(CH.sub.3)CH.sub.2 OMe H Me Me GaCH(CH.sub.3)CH.sub.2 OMe H Me Et GbCH(CH.sub.3 )CH.sub.2 OMe H H CF.sub.3 GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 F GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 Cl GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 Br GbCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 I GbCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 OMe GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 OEt GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 OCH.sub.2 CCH GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 OCHF.sub.2 GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 OCF.sub.3 GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 SMe GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 SEt GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 SO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 SO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 CF.sub.3 GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 CN GaCH(CH.sub.3)CH.sub.2 OMe H H CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 OMe H H CO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 CO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 OMe H H COMe GaCH(CH.sub.3)CH.sub.2 OMe H H COEt GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 COMe GaCH(CH.sub.3)CH.sub.2 OMe H H CH.sub.2 COEt GaCH(CH.sub.3)CH.sub.2 OEt H H H GaCH(CH.sub.3)CH.sub.2 OEt H H Me GbCH(CH.sub.3)CH.sub.2 OEt Me H H GaCH(CH.sub.3)CH.sub.2 OEt Me H Me GbCH(CH.sub.3)CH.sub.2 OEt H Me Me GaCH(CH.sub.3)CH.sub.2 OEt H H CF.sub.3 GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 F GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 Cl GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 Br GbCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 I GbCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 OMe GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 OCH.sub.2 CCH GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 OCHF.sub.2 GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 OCF.sub.3 GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 SMe GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 SO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 CF.sub.3 GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 CN GaCH(CH.sub.3)CH.sub.2 OEt H H CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 OEt H H COMe GaCH(CH.sub.3)CH.sub.2 OEt H H CH.sub.2 COMe GaCH.sub.2 OCHF.sub.2 H H H GaCH.sub.2 OCHF.sub.2 H H Me GbCH.sub.2 OCHF.sub.2 H H Et GbCH.sub.2 OCHF.sub.2 H H Pr-n GbCH.sub.2 OCHF.sub.2 H H Pr-i GbCH.sub.2 OCHF.sub.2 H H Bu-n GcCH.sub.2 OCHF.sub.2 Me H H GaCH.sub.2 OCHF.sub.2 Et H H GbCH.sub.2 OCHF.sub.2 Me H Me GbCH.sub.2 OCHF.sub.2 Me H Et GbCH.sub.2 OCHF.sub.2 H Me Me GaCH.sub.2 OCHF.sub.2 H Me Et GbCH.sub.2 OCHF.sub.2 H H F GaCH.sub.2 OCHF.sub.2 H H Cl GaCH.sub.2 OCHF.sub.2 H H Br GbCH.sub.2 OCHF.sub.2 H H I GbCH.sub.2 OCHF.sub.2 H H CF.sub.3 GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 F GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 Cl GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 Br GbCH.sub.2 OCHF.sub.2 H H CH.sub.2 I GbCH.sub.2 OCHF.sub.2 H H CH.sub.2 CH.sub.2 F GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 OCHF.sub.2 H H CH.sub.2 CH.sub.2 I GbCH.sub.2 OCHF.sub.2 H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 OCHF.sub. 2 H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 OCHF.sub.2 H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 OCHF.sub.2 H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 OCHF.sub.2 H H CH.sub.2 OMe GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 OEt GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 OCHF.sub.2 H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 OCHF.sub.2 H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 OCHF.sub.2 H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 OCF.sub.3 GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 SMe GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 SEt GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 SO.sub. 2 Et GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CF.sub.3 GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CN GaCH.sub.2 OCHF.sub.2 H H CO.sub.2 Me GaCH.sub.2 OCHF.sub.2 H H CO.sub.2 Et GaCH.sub.2 OCHF.sub.2 H H CO.sub.2 Pr-n GbCH.sub.2 OCHF.sub.2 H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 OCHF.sub.2 H H COMe GaCH.sub.2 OCHF.sub.2 H H COEt GbCH.sub.2 OCHF.sub.2 H H COPr-n GbCH.sub.2 OCHF.sub.2 H H CH.sub.2 COMe GaCH.sub.2 OCHF.sub.2 H H CH.sub.2 COEt GaCH.sub.2 SMe H H H GaCH.sub.2 SMe H H Me GbCH.sub.2 SMe H H Et GbCH.sub.2 SMe H H Pr-n GbCH.sub.2 SMe H H Pr-i GbCH.sub.2 SMe H H Bu-n GcCH.sub.2 SMe Me H H GaCH.sub.2 SMe Et H H GbCH.sub.2 SMe Me H Me GbCH.sub.2 SMe Me H Et GbCH.sub.2 SMe H Me Me GaCH.sub.2 SMe H Me Et GbCH.sub.2 SMe H H F GaCH.sub.2 SMe H H Cl GaCH.sub.2 SMe H H Br GbCH.sub.2 SMe H H I GbCH.sub.2 SMe H H CF.sub.3 GaCH.sub.2 SMe H H CH.sub.2 F GaCH.sub.2 SMe H H CH.sub.2 Cl GaCH.sub.2 SMe H H CH.sub.2 Br GbCH.sub.2 SMe H H CH.sub.2 I GbCH.sub.2 SMe H H CH.sub.2 CH.sub.2 F GaCH.sub.2 SMe H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 SMe H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 SMe H H CH.sub.2 CH.sub.2 I GbCH.sub.2 SMe H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 SMe H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 SMe H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 SMe H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 SMe H H CH.sub.2 OMe GaCH.sub.2 SMe H H CH.sub.2 OEt GaCH.sub.2 SMe H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 SMe H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 SMe H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 SMe H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 SMe H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 SMe H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 SMe H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 SMe H H CH.sub.2 OCF.sub.3 GaCH.sub.2 SMe H H CH.sub.2 SMe GaCH.sub.2 SMe H H CH.sub.2 SEt GaCH.sub.2 SMe H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 SMe H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 SMe H H CH.sub.2 CF.sub.3 GaCH.sub.2 SMe H H CH.sub.2 CN GaCH.sub.2 SMe H H CO.sub.2 Me GaCH.sub.2 SMe H H CO.sub.2 Et GaCH.sub.2 SMe H H CO.sub.2 Pr-n GbCH.sub.2 SMe H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 SMe H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 SMe H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 SMe H H COMe GaCH.sub.2 SMe H H COEt GaCH.sub.2 SMe H H COPr-n GbCH.sub.2 SMe H H CH.sub.2 COMe GaCH.sub.2 SMe H H CH.sub.2 COEt GaCH.sub.2 SEt H H H GaCH.sub.2 SEt H H Me GbCH.sub.2 SEt H H Et GbCH.sub.2 SEt Me H H GaCH.sub.2 SEt Et H H GbCH.sub.2 SEt Me H Me GbCH.sub.2 SEt Me H Et GbCH.sub.2 SEt H Me Me GaCH.sub.2 SEt H Me Et GbCH.sub.2 SEt H H CF.sub.3 GaCH.sub.2 SEt H H CH.sub.2 F GaCH.sub.2 SEt H H CH.sub.2 Cl GaCH.sub.2 SEt H H CH.sub.2 Br GbCH.sub.2 SEt H H CH.sub.2 I GbCH.sub.2 SEt H H CH.sub.2 OMe GaCH.sub.2 SEt H H CH.sub.2 OEt GaCH.sub.2 SEt H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 SEt H H CH.sub.2 OCH.sub.2 C CH GaCH.sub.2 SEt H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 SEt H H CH.sub.2 OCF.sub.3 GaCH.sub.2 SEt H H CH.sub.2 SMe GaCH.sub.2 SEt H H CH.sub.2 SEt GaCH.sub.2 SEt H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 SEt H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 SEt H H CH.sub.2 CF.sub.3 GaCH.sub.2 SEt H H CH.sub.2 CN GaCH.sub.2 SEt H H CO.sub.2 Me GaCH.sub.2 SEt H H CO.sub.2 Et GaCH.sub.2 SEt H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 SEt H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 SEt H H COMe GaCH.sub.2 SEt H H COEt GaCH.sub.2 SEt H H CH.sub.2 COMe GaCH.sub.2 SEt H H CH.sub.2 COEt GaCH.sub.2 SEt H H CH.sub.2 COMe GaCH.sub.2 SEt H H CH.sub.2 COEt GaCH.sub.2 SO.sub.2 Me H H H GaCH.sub.2 SO.sub.2 Me H H Me GbCH.sub.2 SO.sub.2 Me H H Et GbCH.sub.2 SO.sub.2 Me H H Pr-n GbCH.sub.2 SO.sub.2 Me H H Pr-i GbCH.sub.2 SO.sub.2 Me H H Bu-n GcCH.sub.2 SO.sub.2 Me Me H H GaCH.sub.2 SO.sub.2 Me Et H H GbCH.sub.2 SO.sub.2 Me Me H Me GbCH.sub.2 SO.sub.2 Me Me H Et GbCH.sub.2 SO.sub.2 Me H Me Me GaCH.sub.2 SO.sub.2 Me H Me Et GbCH.sub.2 SO.sub.2 Me H H F GaCH.sub.2 SO.sub.2 Me H H Cl GaCH.sub.2 SO.sub.2 Me H H Br GbCH.sub.2 SO.sub.2 Me H H I GbCH.sub.2 SO.sub.2 Me H H CF.sub.3 GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 F GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 Cl GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 Br GbCH.sub.2 SO.sub.2 Me H H CH.sub.2 I GbCH.sub.2 SO.sub.2 Me H H CH.sub.2 CH.sub.2 F GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 SO.sub.2 Me H H CH.sub.2 CH.sub.2 I GbCH.sub.2 SO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 SO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 SO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 SO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 SO.sub.2 Me H H CH.sub.2 OMe GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 OEt GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 SO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 SO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 SO.sub.2 Me H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 OCF.sub.3 GaCH.sub. 2 SO.sub.2 Me H H CH.sub.2 SMe GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 SEt GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CF.sub.3 GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CN GaCH.sub.2 SO.sub.2 Me H H CO.sub.2 Me GaCH.sub.2 SO.sub.2 Me H H CO.sub.2 Et GaCH.sub.2 SO.sub.2 Me H H CO.sub.2 Pr-n GbCH.sub.2 SO.sub.2 Me H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 SO.sub.2 Me H H COMe GaCH.sub.2 SO.sub.2 Me H H COEt GaCH.sub.2 SO.sub.2 Me H H COPr-n GbCH.sub.2 SO.sub.2 Me H H CH.sub.2 COMe GaCH.sub.2 SO.sub.2 Me H H CH.sub.2 COEt GaCH.sub.2 SO.sub.2 Et H H H GaCH.sub.2 SO.sub.2 Et H H Me GbCH.sub.2 SO.sub.2 Et H H Et GbCH.sub.2 SO.sub.2 Et Me H H GaCH.sub.2 SO.sub.2 Et Et H H GbCH.sub.2 SO.sub.2 Et Me H Me GbCH.sub.2 SO.sub.2 Et Me H Et GbCH.sub.2 SO.sub.2 Et H Me Me GaCH.sub.2 SO.sub.2 Et H Me Et GbCH.sub.2 SO.sub.2 Et H H CF.sub.3 GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 F GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 Cl GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 Br GbCH.sub.2 SO.sub.2 Et H H CH.sub.2 I GbCH.sub.2 SO.sub.2 Et H H CH.sub.2 OMe GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 OEt GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 OCF.sub.3 GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 SMe GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 SEt GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 CF.sub.3 GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 CN GaCH.sub.2 SO.sub.2 Et H H CO.sub.2 Me GaCH.sub.2 SO.sub.2 Et H H CO.sub.2 Et GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 SO.sub.2 Et H H COMe GaCH.sub.2 SO.sub.2 Et H H COEt GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 COMe GaCH.sub.2 SO.sub.2 Et H H CH.sub.2 COEt GaCH.sub.2 F H H H GaCH.sub.2 F H H Me GbCH.sub.2 F H H Et GbCH.sub.2 F H H Pr-n GbCH.sub.2 F H H Pr-i GbCH.sub.2 F H H Bu-n GcCH.sub.2 F Me H H GaCH.sub.2 F Et H H GbCH.sub.2 F Me H Me GbCH.sub.2 F Me H Et GbCH.sub.2 F H Me Me GaCH.sub.2 F H Me Et GbCH.sub.2 F H H F GaCH.sub.2 F H H Cl GaCH.sub.2 F H H Br GbCH.sub.2 F H H I GbCH.sub.2 F H H CF.sub.3 GaCH.sub.2 F H H CH.sub.2 F GaCH.sub.2 F H H CH.sub.2 Cl GaCH.sub.2 F H H CH.sub.2 Br GbCH.sub.2 F H H CH.sub.2 I GbCH.sub.2 F H H CH.sub.2 CH.sub.2 F GaCH.sub.2 F H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 F H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 F H H CH.sub.2 CH.sub.2 I GbCH.sub.2 F H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 F H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 F H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 F H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 F H H CH.sub.2 OMe GaCH.sub.2 F H H CH.sub.2 OEt GaCH.sub.2 F H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 F H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 F H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 F H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 F H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 F H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 F H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 F H H CH.sub.2 OCF.sub.3 GaCH.sub.2 F H H CH.sub.2 SMe GaCH.sub.2 F H H CH.sub.2 SEt GaCH.sub.2 F H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 F H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 F H H CH.sub.2 CF.sub.3 GaCH.sub.2 F H H CH.sub.2 CN GaCH.sub.2 F H H CO.sub.2 Me GaCH.sub.2 F H H CO.sub.2 Et GaCH.sub.2 F H H CO.sub.2 Pr-n GbCH.sub.2 F H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 F H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 F H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 F H H COMe GaCH.sub.2 F H H COEt GaCH.sub.2 F H H COPr-n GbCH.sub.2 F H H CH.sub.2 COMe GaCH.sub.2 F H H CH.sub.2 COEt GaCH.sub.2 Cl H H H GaCH.sub.2 Cl H H Me GbCH.sub.2 Cl H H Et GbCH.sub.2 Cl H H Pr-n GbCH.sub.2 Cl H H Pr-i GbCH.sub.2 Cl H H Bu-n GcCH.sub.2 Cl Me H H GaCH.sub.2 Cl Et H H GbCH.sub.2 Cl Me H Me GbCH.sub.2 Cl Me H Et GbCH.sub.2 Cl H Me Me GaCH.sub.2 Cl H Me Et GbCH.sub.2 Cl H H F GaCH.sub.2 Cl H H Cl GaCH.sub.2 Cl H H Br GbCH.sub.2 Cl H H I GbCH.sub. 2 Cl H H CF.sub.3 GaCH.sub.2 Cl H H CH.sub.2 F GaCH.sub.2 Cl H H CH.sub.2 Cl GaCH.sub.2 Cl H H CH.sub.2 Br GbCH.sub.2 Cl H H CH.sub.2 I GbCH.sub.2 Cl H H CH.sub.2 CH.sub.2 F GaCH.sub.2 Cl H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 Cl H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 Cl H H CH.sub.2 CH.sub.2 I GbCH.sub.2 Cl H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 Cl H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 Cl H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 Cl H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 Cl H H CH.sub.2 OMe GaCH.sub.2 Cl H H CH.sub.2 OEt GaCH.sub.2 Cl H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 Cl H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 Cl H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 Cl H H CH(CH.sub.3)CH.sub. 2 OEt GbCH.sub.2 Cl H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 Cl H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 Cl H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 Cl H H CH.sub.2 OCF.sub.3 GaCH.sub.2 Cl H H CH.sub.2 SMe GaCH.sub.2 Cl H H CH.sub.2 SEt GaCH.sub.2 Cl H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 Cl H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 Cl H H CH.sub.2 CF.sub.3 GaCH.sub.2 Cl H H CH.sub.2 CN GaCH.sub.2 Cl H H CO.sub.2 Me GaCH.sub.2 Cl H H CO.sub.2 Et GaCH.sub.2 Cl H H CO.sub.2 Pr-n GbCH.sub.2 Cl H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 Cl H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 Cl H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 Cl H H COMe GaCH.sub.2 Cl H H COEt GaCH.sub.2 Cl H H COPr-n GbCH.sub.2 Cl H H CH.sub.2 COMe GaCH.sub.2 Cl H H CH.sub.2 COEt GaCH.sub.2 Br H H H GaCH.sub.2 Br H H Me GbCH.sub.2 Br H H Et GbCH.sub.2 Br Me H H GaCH.sub.2 Br Et H H GbCH.sub.2 Br Me H Me GbCH.sub.2 Br Me H Et GbCH.sub.2 Br H Me Me GaCH.sub.2 Br H Me Et GbCH.sub.2 Br H H CF.sub.3 GaCH.sub.2 Br H H CH.sub.2 F GaCH.sub.2 Br H H CH.sub.2 Cl GaCH.sub.2 Br H H CH.sub.2 Br GbCH.sub.2 Br H H CH.sub.2 I GbCH.sub.2 Br H H CH.sub.2 OMe GaCH.sub.2 Br H H CH.sub.2 OEt GaCH.sub.2 Br H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 Br H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 Br H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 Br H H CH.sub.2 OCF.sub.3 GaCH.sub.2 Br H H CH.sub.2 SMe GaCH.sub.2 Br H H CH.sub.2 SEt GaCH.sub.2 Br H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 Br H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 Br H H CH.sub.2 CF.sub.3 GaCH.sub.2 Br H H CH.sub.2 CN GaCH.sub.2 Br H H CO.sub.2 Me GaCH.sub.2 Br H H CO.sub.2 Et GaCH.sub.2 Br H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 Br H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 Br H H COMe GaCH.sub.2 Br H H COEt GaCH.sub.2 Br H H CH.sub.2 COMe GaCH.sub.2 Br H H CH.sub.2 COEt GaCH.sub.2 I H H H GaCH.sub.2 I H H Me GbCH.sub.2 I H H Et GbCH.sub.2 I Me H H GaCH.sub.2 I Et H H GbCH.sub.2 I Me H Me GbCH.sub.2 I Me H Et GbCH.sub.2 I H Me Me GaCH.sub.2 I H Me Et GbCH.sub.2 I H H CF.sub.3 GaCH.sub.2 I H H CH.sub.2 F GaCH.sub.2 I H H CH.sub.2 Cl GaCH.sub.2 I H H CH.sub.2 Br GbCH.sub.2 I H H CH.sub.2 I GbCH.sub.2 I H H CH.sub.2 OMe GaCH.sub.2 I H H CH.sub.2 OEt GaCH.sub.2 I H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 I H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 I H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 I H H CH.sub.2 OCF.sub.3 GaCH.sub.2 I H H CH.sub.2 SMe GaCH.sub.2 I H H CH.sub.2 SEt GaCH.sub.2 I H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 I H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 I H H CH.sub.2 CF.sub.3 GaCH.sub.2 I H H CH.sub.2 CN GaCH.sub.2 I H H CO.sub.2 Me GaCH.sub.2 I H H CO.sub.2 Et GaCH.sub.2 I H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 I H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 I H H COMe GaCH.sub.2 I H H COEt GaCH.sub.2 I H H CH.sub.2 COMe GaCH.sub.2 I H H CH.sub.2 COEt GaCH.sub.2 CH.sub.2 F H H H GaCH.sub.2 CH.sub.2 F H H Me GbCH.sub.2 CH.sub.2 F H H Et GbCH.sub.2 CH.sub.2 F Me H H GaCH.sub.2 CH.sub.2 F Et H H GbCH.sub.2 CH.sub.2 F Me H Me GbCH.sub.2 CH.sub.2 F Me H Et GbCH.sub.2 CH.sub.2 F H Me Me GaCH.sub.2 CH.sub.2 F H Me Et GbCH.sub.2 CH.sub.2 F H H CF.sub.3 GaCH.sub.2 CH.sub.2 F H H CH.sub.2 F GaCH.sub.2 CH.sub.2 F H H CH.sub.2 Cl GaCH.sub.2 CH.sub.2 F H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 F H H CH.sub.2 I GbCH.sub.2 CH.sub.2 F H H CH.sub.2 OMe GaCH.sub.2 CH.sub.2 F H H CH.sub.2 OEt GaCH.sub.2 CH.sub.2 F H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CH.sub. 2 F H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CH.sub.2 F H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CH.sub.2 F H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CH.sub.2 F H H CH.sub.2 SMe GaCH.sub.2 CH.sub.2 F H H CH.sub.2 SEt GaCH.sub.2 CH.sub.2 F H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CH.sub.2 F H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CH.sub.2 F H H CH.sub.2 CF.sub.3 GaCH.sub.2 CH.sub.2 F H H CH.sub.2 CN GaCH.sub.2 CH.sub.2 F H H CO.sub.2 Me GaCH.sub.2 CH.sub.2 F H H CO.sub.2 Et GaCH.sub.2 CH.sub.2 F H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CH.sub.2 F H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CH.sub.2 F H H COMe GaCH.sub.2 CH.sub.2 F H H COEt GaCH.sub.2 CH.sub.2 F H H CH.sub.2 COMe GaCH.sub.2 CH.sub.2 F H H CH.sub.2 COEt GaCH.sub.2 CH.sub.2 Cl H H H GaCH.sub.2 CH.sub.2 Cl H H Me GbCH.sub.2 CH.sub.2 Cl H H Et GbCH.sub.2 CH.sub.2 Cl Me H H GaCH.sub.2 CH.sub.2 Cl Et H H GbCH.sub.2 CH.sub.2 Cl Me H Me GbCH.sub.2 CH.sub.2 Cl Me H Et GbCH.sub.2 CH.sub.2 Cl H Me Me GaCH.sub.2 CH.sub.2 Cl H Me Et GbCH.sub.2 CH.sub.2 Cl H H CF.sub.3 GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 F GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 Cl GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 Cl H H CH.sub.2 I GbCH.sub.2 CH.sub.2 Cl H H CH.sub.2 OMe GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 OEt GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CH.sub. 2 Cl H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 SMe GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 SEt GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 CF.sub.3 GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 CN GaCH.sub.2 CH.sub.2 Cl H H CO.sub.2 Me GaCH.sub.2 CH.sub.2 Cl H H CO.sub.2 Et GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CH.sub.2 Cl H H COMe GaCH.sub.2 CH.sub.2 Cl H H COEt GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 COMe GaCH.sub.2 CH.sub.2 Cl H H CH.sub.2 COEt GaCH.sub.2 CH.sub.2 Br H H H GaCH.sub.2 CH.sub.2 Br H H Me GbCH.sub.2 CH.sub.2 Br Me H H GaCH.sub.2 CH.sub.2 Br Me H Me GbCH.sub.2 CH.sub.2 Br H Me Me GaCH.sub.2 CH.sub.2 Br H H CF.sub.3 GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 F GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 Cl GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 Br H H CH.sub.2 I GbCH.sub.2 CH.sub.2 Br H H CH.sub.2 OMe GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 SMe GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 CF.sub.3 GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 CN GaCH.sub. 2 CH.sub.2 Br H H CO.sub.2 Me GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CH.sub.2 Br H H COMe GaCH.sub.2 CH.sub.2 Br H H CH.sub.2 COMe GaCH.sub.2 CH.sub.2 I H H H GaCH.sub.2 CH.sub.2 I H H Me GbCH.sub.2 CH.sub.2 I Me H H GaCH.sub.2 CH.sub.2 I Me H Me GbCH.sub.2 CH.sub.2 I H Me Me GaCH.sub.2 CH.sub.2 I H H CF.sub.3 GaCH.sub.2 CH.sub.2 I H H CH.sub.2 F GaCH.sub.2 CH.sub.2 I H H CH.sub.2 Cl GaCH.sub.2 CH.sub.2 I H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 I H H CH.sub.2 I GbCH.sub.2 CH.sub.2 I H H CH.sub.2 OMe GaCH.sub.2 CH.sub.2 I H H CH.sub.2 OCH.sub.2 CH CH.sub.2 GaCH.sub.2 CH.sub.2 I H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CH.sub.2 I H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CH.sub.2 I H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CH.sub.2 I H H CH.sub.2 SMe GaCH.sub.2 CH.sub.2 I H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CH.sub.2 I H H CH.sub.2 CF.sub.3 GaCH.sub.2 CH.sub.2 I H H CH.sub.2 CN GaCH.sub.2 CH.sub.2 I H H CO.sub.2 Me GaCH.sub.2 CH.sub.2 I H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CH.sub.2 I H H COMe GaCH.sub.2 CH.sub.2 I H H CH.sub.2 COMe GaCH(CH.sub.3)CH.sub.2 F H H H GaCH(CH.sub.3)CH.sub.2 F H H Me GbCH(CH.sub.3)CH.sub.2 F H H Et GbCH(CH.sub.3)CH.sub.2 F Me H H GaCH(CH.sub.3)CH.sub.2 F Et H H GbCH(CH.sub.3)CH.sub.2 F Me H Me GbCH(CH.sub.3)CH.sub.2 F Me H Et GbCH(CH.sub.3)CH.sub.2 F H Me Me GaCH(CH.sub.3)CH.sub.2 F H Me Et GbCH(CH.sub.3)CH.sub.2 F H H CF.sub.3 GaCH(CH.sub.3)CH.sub. 2 F H H CH.sub.2 F GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 Cl GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 Br GbCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 I GbCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 OMe GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 OEt GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 OCH.sub.2 CCH GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 OCHF.sub.2 GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 OCF.sub.3 GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 SMe GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 SEt GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 SO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 SO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 CF.sub.3 GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 CN GaCH(CH.sub.3)CH.sub.2 F H H CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 F H H CO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 CO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 F H H COMe GaCH(CH.sub.3)CH.sub.2 F H H COEt GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 COMe GaCH(CH.sub.3)CH.sub.2 F H H CH.sub.2 COEt GaCH(CH.sub.3)CH.sub.2 Cl H H H GaCH(CH.sub.3)CH.sub.2 Cl H H Me GbCH(CH.sub.3)CH.sub.2 Cl H H Et GbCH(CH.sub.3)CH.sub.2 Cl Me H H GaCH(CH.sub.3)CH.sub.2 Cl Et H H GbCH(CH.sub.3)CH.sub.2 Cl Me H Me GbCH(CH.sub.3)CH.sub.2 Cl Me H Et GbCH(CH.sub.3)CH.sub.2 Cl H Me Me GaCH(CH.sub.3)CH.sub.2 Cl H Me Et GbCH(CH.sub.3)CH.sub.2 Cl H H CF.sub.3 GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 F GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 Cl GaCH(CH.sub.3)CH.sub. 2 Cl H H CH.sub.2 Br GbCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 I GbCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 OMe GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 OEt GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 OCH.sub.2 CH CH.sub.2 GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 OCH.sub.2 CCH GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 OCHF.sub.2 GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 OCF.sub.3 GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 SMe GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 SEt GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 SO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 SO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 CF.sub.3 GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 CN GaCH(CH.sub.3)CH.sub.2 Cl H H CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 Cl H H CO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 CO.sub.2 Et GaCH(CH.sub.3)CH.sub.2 Cl H H COMe GaCH(CH.sub.3)CH.sub.2 Cl H H COEt GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 COMe GaCH(CH.sub.3)CH.sub.2 Cl H H CH.sub.2 COEt GaCH(CH.sub.3)CH.sub.2 Br H H H GaCH(CH.sub.3)CH.sub.2 Br H H Me GbCH(CH.sub.3)CH.sub.2 Br Me H H GaCH(CH.sub.3)CH.sub.2 Br Me H Me GbCH(CH.sub.3)CH.sub.2 Br H Me Me GaCH(CH.sub.3)CH.sub.2 Br H H CF.sub.3 GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 F GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 Cl GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 Br GbCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 I GbCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 OMe GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 OCH.sub.2 CCH GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 OCHF.sub.2 GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 OCF.sub.3 GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 SMe GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 SO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 CF.sub.3 GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 CN GaCH(CH.sub.3)CH.sub.2 Br H H CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 Br H H COMe GaCH(CH.sub.3)CH.sub.2 Br H H CH.sub.2 COMe GaCH(CH.sub.3)CH.sub.2 I H H H GaCH(CH.sub.3)CH.sub.2 I H H Me GbCH(CH.sub.3)CH.sub.2 I Me H H GaCH(CH.sub.3)CH.sub.2 I Me H Me GbCH(CH.sub.3)CH.sub.2 I H Me Me GaCH(CH.sub.3)CH.sub.2 I H H CF.sub.3 GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 F GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 Cl GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 Br GbCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 I GbCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 OMe GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 OCH.sub.2 CCH GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 OCHF.sub.2 GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 OCF.sub.3 GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 SMe GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 SO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 CF.sub.3 GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 CN GaCH(CH.sub.3)CH.sub.2 I H H CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 CO.sub.2 Me GaCH(CH.sub.3)CH.sub.2 I H H COMe GaCH(CH.sub.3)CH.sub.2 I H H CH.sub.2 COMe GaCH.sub.2 CF.sub. 3 H H H GaCH.sub.2 CF.sub.3 H H Me GbCH.sub.2 CF.sub.3 H H Et GbCH.sub.2 CF.sub.3 H H Pr-n GbCH.sub.2 CF.sub.3 H H Pr-i GbCH.sub.2 CF.sub.3 H H Bu-n GcCH.sub.2 CF.sub.3 Me H H GaCH.sub.2 CF.sub.3 Et H H GbCH.sub.2 CF.sub.3 Me H Me GbCH.sub.2 CF.sub.3 Me H Et GbCH.sub.2 CF.sub.3 H Me Me GaCH.sub.2 CF.sub.3 H Me Et GbCH.sub.2 CF.sub.3 H H F GaCH.sub.2 CF.sub.3 H H Cl GaCH.sub.2 CF.sub.3 H H Br GbCH.sub.2 CF.sub.3 H H I GbCH.sub.2 CF.sub.3 H H CF.sub.3 GaCH.sub.2 CF.sub.3 H H CH.sub.2 F GaCH.sub.2 CF.sub.3 H H CH.sub.2 Cl GaCH.sub.2 CF.sub.3 H H CH.sub.2 Br GbCH.sub.2 CF.sub.3 H H CH.sub.2 I GbCH.sub.2 CF.sub.3 H H CH.sub.2 CH.sub.2 F GaCH.sub.2 CF.sub.3 H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 CF.sub.3 H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 CF.sub.3 H H CH.sub.2 CH.sub.2 I GbCH.sub.2 CF.sub.3 H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 CF.sub.3 H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 CF.sub.3 H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 CF.sub.3 H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 CF.sub.3 H H CH.sub.2 OMe GaCH.sub.2 CF.sub.3 H H CH.sub.2 OEt GaCH.sub.2 CF.sub.3 H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 CF.sub.3 H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 CF.sub.3 H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 CF.sub.3 H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 CF.sub.3 H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CF.sub.3 H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CF.sub.3 H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CF.sub.3 H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CF.sub.3 H H CH.sub.2 SMe GaCH.sub.2 CF.sub.3 H H CH.sub.2 SEt GaCH.sub.2 CF.sub.3 H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CF.sub.3 H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CF.sub.3 H H CH.sub.2 CF.sub.3 GaCH.sub.2 CF.sub.3 H H CH.sub.2 CN GaCH.sub.2 CF.sub.3 H H CO.sub.2 Me GaCH.sub.2 CF.sub.3 H H CO.sub.2 Et GaCH.sub.2 CF.sub.3 H H CO.sub.2 Pr-n GbCH.sub.2 CF.sub.3 H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CF.sub.3 H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CF.sub.3 H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 CF.sub.3 H H COMe GaCH.sub.2 CF.sub.3 H H COEt GaCH.sub.2 CF.sub.3 H H COPr-n GbCH.sub.2 CF.sub.3 H H CH.sub.2 COMe GaCH.sub.2 CF.sub.3 H H CH.sub.2 COEt GaCH.sub.2 CN H H H GaCH.sub.2 CN H H Me GbCH.sub.2 CN H H Et GbCH.sub.2 CN H H Pr-n GbCH.sub. 2 CN H H Pr-i GbCH.sub.2 CN H H Bu-n GcCH.sub.2 CN Me H H GaCH.sub.2 CN Et H H GbCH.sub.2 CN Me H Me GbCH.sub.2 CN Me H Et GbCH.sub.2 CN H Me Me GaCH.sub.2 CN H Me Et GbCH.sub.2 CN H H F GaCH.sub.2 CN H H Cl GaCH.sub.2 CN H H Br GbCH.sub.2 CN H H I GbCH.sub.2 CN H H CF.sub.3 GaCH.sub.2 CN H H CH.sub.2 F GaCH.sub.2 CN H H CH.sub.2 Cl GaCH.sub.2 CN H H CH.sub.2 Br GbCH.sub.2 CN H H CH.sub.2 I GbCH.sub.2 CN H H CH.sub.2 CH.sub.2 F GaCH.sub.2 CN H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 CN H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 CN H H CH.sub.2 CH.sub.2 I GbCH.sub.2 CN H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 CN H H CH(CH.sub.3)CH.sub.2 Cl Ga -CH.sub.2 CN H H CH(CH.sub.3 )CH.sub.2 Br GbCH.sub.2 CN H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 CN H H CH.sub.2 OMe GaCH.sub.2 CN H H CH.sub.2 OEt GaCH.sub.2 CN H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 CN H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 CN H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 CN H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 CN H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CN H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CN H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CN H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CN H H CH.sub.2 SMe GaCH.sub.2 CN H H CH.sub.2 SEt GaCH.sub.2 CN H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CN H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CN H H CH.sub.2 CF.sub.3 GaCH.sub.2 CN H H CH.sub.2 CN GaCH.sub.2 CN H H CO.sub.2 Me GaCH.sub. 2 CN H H CO.sub.2 Et GaCH.sub.2 CN H H CO.sub.2 Pr-n GbCH.sub.2 CN H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CN H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CN H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 CN H H COMe GaCH.sub.2 CN H H COEt GaCH.sub.2 CN H H COPr-n GbCH.sub.2 CN H H CH.sub.2 COMe GaCH.sub.2 CN H H CH.sub.2 COEt GaCH.sub.2 CO.sub.2 Me H H H GaCH.sub.2 CO.sub.2 Me H H Me GbCH.sub.2 CO.sub.2 Me H H Et GbCH.sub.2 CO.sub.2 Me H H Pr-n GbCH.sub.2 CO.sub.2 Me H H Pr-i GbCH.sub.2 CO.sub.2 Me H H Bu-n GcCH.sub.2 CO.sub.2 Me Me H H GaCH.sub.2 CO.sub.2 Me Et H H GbCH.sub.2 CO.sub.2 Me Me H Me GbCH.sub.2 CO.sub.2 Me Me H Et GbCH.sub.2 CO.sub.2 Me H Me Me GaCH.sub.2 CO.sub.2 Me H Me Et GbCH.sub.2 CO.sub. 2 Me H H F GaCH.sub.2 CO.sub.2 Me H H Cl GaCH.sub.2 CO.sub.2 Me H H Br GbCH.sub.2 CO.sub.2 Me H H I GbCH.sub.2 CO.sub.2 Me H H CF.sub.3 GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 F GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 Cl GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 Br GbCH.sub.2 CO.sub.2 Me H H CH.sub.2 I GbCH.sub.2 CO.sub.2 Me H H CH.sub.2 CH.sub.2 F GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 CO.sub.2 Me H H CH.sub.2 CH.sub.2 I GbCH.sub.2 CO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 CO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 CO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 CO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 I GbCH.sub.2 CO.sub.2 Me H H CH.sub.2 OMe GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 OEt GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 CO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 CO.sub.2 Me H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 CO.sub.2 Me H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 SMe GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 SEt GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CF.sub.3 GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CN GaCH.sub.2 CO.sub.2 Me H H CO.sub.2 Me GaCH.sub.2 CO.sub.2 Me H H CO.sub.2 Et GaCH.sub.2 CO.sub.2 Me H H CO.sub.2 Pr-n GbCH.sub.2 CO.sub.2 Me H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 CO.sub.2 Me H H COMe GaCH.sub.2 CO.sub.2 Me H H COEt GaCH.sub.2 CO.sub.2 Me H H COPr-n GbCH.sub.2 CO.sub.2 Me H H CH.sub.2 COMe GaCH.sub.2 CO.sub.2 Me H H CH.sub.2 COEt GaCH.sub.2 CO.sub.2 Et H H H GaCH.sub.2 CO.sub.2 Et H H Me GbCH.sub.2 CO.sub.2 Et H H Et GbCH.sub.2 CO.sub.2 Et Me H H GaCH.sub.2 CO.sub.2 Et Et H H GbCH.sub.2 CO.sub.2 Et Me H Me GbCH.sub.2 CO.sub.2 Et Me H Et GbCH.sub.2 CO.sub.2 Et H Me Me GaCH.sub.2 CO.sub.2 Et H Me Et GbCH.sub.2 CO.sub.2 Et H H CF.sub.3 GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 F GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 Cl GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 Br GbCH.sub.2 CO.sub.2 Et H H CH.sub.2 I GbCH.sub.2 CO.sub.2 Et H H CH.sub.2 OMe GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 OEt GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 SMe GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 SEt GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 CF.sub.3 GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 CN GaCH.sub.2 CO.sub.2 Et H H CO.sub.2 Me GaCH.sub.2 CO.sub.2 Et H H CO.sub.2 Et GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CO.sub.2 Et H H COMe GaCH.sub.2 CO.sub.2 Et H H COEt GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 COMe GaCH.sub.2 CO.sub.2 Et H H CH.sub.2 COEt GaCH.sub.2 CO.sub.2 Pr-n H H H GaCH.sub.2 CO.sub.2 Pr-n H H Me GbCH.sub.2 CO.sub.2 Pr-n Me H H GaCH.sub.2 CO.sub.2 Pr-n Me H Me GbCH.sub.2 CO.sub.2 Pr-n H Me Me GaCH.sub.2 CO.sub.2 Pr-n H H CF.sub.3 GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 F GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 Cl GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 Br GbCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 I GbCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 OMe GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 SMe GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 CF.sub.3 GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 CN GaCH.sub.2 CO.sub.2 Pr-n H H CO.sub.2 Me GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CO.sub.2 Pr-n H H COMe GaCH.sub.2 CO.sub.2 Pr-n H H CH.sub.2 COMe GaCH.sub.2 COMe H H H GaCH.sub.2 COMe H H Me GbCH.sub.2 COMe H H Et GbCH.sub.2 COMe H H Pr-n GbCH.sub.2 COMe H H Pr-i GbCH.sub.2 COMe H H Bu-n GcCH.sub.2 COMe Me H H GaCH.sub.2 COMe Et H H GbCH.sub.2 COMe Me H Me GbCH.sub.2 COMe Me H Et GbCH.sub.2 COMe H Me Me GaCH.sub.2 COMe H Me Et GbCH.sub.2 COMe H H F GaCH.sub.2 COMe H H Cl GaCH.sub.2 COMe H H Br GbCH.sub.2 COMe H H I GbCH.sub.2 COMe H H CF.sub.3 GaCH.sub.2 COMe H H CH.sub.2 F GaCH.sub.2 COMe H H CH.sub.2 Cl GaCH.sub.2 COMe H H CH.sub.2 Br GbCH.sub.2 COMe H H CH.sub.2 I GbCH.sub.2 COMe H H CH.sub.2 CH.sub.2 F GaCH.sub.2 COMe H H CH.sub.2 CH.sub.2 Cl GaCH.sub.2 COMe H H CH.sub.2 CH.sub.2 Br GbCH.sub.2 COMe H H CH.sub.2 CH.sub.2 I GbCH.sub.2 COMe H H CH(CH.sub.3)CH.sub.2 F GaCH.sub.2 COMe H H CH(CH.sub.3)CH.sub.2 Cl GaCH.sub.2 COMe H H CH(CH.sub.3)CH.sub.2 Br GbCH.sub.2 COMe H H CH(CH.sub.3 )CH.sub.2 I GbCH.sub.2 COMe H H CH.sub.2 OMe GaCH.sub.2 COMe H H CH.sub.2 OEt GaCH.sub.2 COMe H H CH.sub.2 CH.sub.2 OMe GaCH.sub.2 COMe H H CH.sub.2 CH.sub.2 OEt GaCH.sub.2 COMe H H CH(CH.sub.3)CH.sub.2 OMe GbCH.sub.2 COMe H H CH(CH.sub.3)CH.sub.2 OEt GbCH.sub.2 COMe H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 COMe H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 COMe H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 COMe H H CH.sub.2 OCF.sub.3 GaCH.sub.2 COMe H H CH.sub.2 SMe GaCH.sub.2 COMe H H CH.sub.2 SEt GaCH.sub.2 COMe H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 COMe H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 COMe H H CH.sub.2 CF.sub.3 GaCH.sub.2 COMe H H CH.sub.2 CN GaCH.sub.2 COMe H H CO.sub.2 Me GaCH.sub.2 COMe H H CO.sub.2 Et GaCH.sub.2 COMe H H CO.sub.2 Pr-n GbCH.sub.2 COMe H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 COMe H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 COMe H H CH.sub.2 CO.sub.2 Pr-n GbCH.sub.2 COMe H H COMe GaCH.sub.2 COMe H H COEt GaCH.sub.2 COMe H H COPr-n GbCH.sub.2 COMe H H CH.sub.2 COMe GaCH.sub.2 COMe H H CH.sub.2 COEt GaCH.sub.2 COEt H H H GaCH.sub.2 COEt H H Me GbCH.sub.2 COEt H H Et GbCH.sub.2 COEt Me H H GaCH.sub.2 COEt Et H H GbCH.sub.2 COEt Me H Me GbCH.sub.2 COEt Me H Et GbCH.sub.2 COEt H Me Me GaCH.sub.2 COEt H Me Et GbCH.sub.2 COEt H H CF.sub.3 GaCH.sub.2 COEt H H CH.sub.2 F GaCH.sub.2 COEt H H CH.sub.2 Cl GaCH.sub.2 COEt H H CH.sub.2 Br GbCH.sub.2 COEt H H CH.sub.2 I GbCH.sub.2 COEt H H CH.sub.2 OMe GaCH.sub.2 COEt H H CH.sub. 2 OEt GaCH.sub.2 COEt H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 COEt H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 COEt H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 COEt H H CH.sub.2 OCF.sub.3 GaCH.sub.2 COEt H H CH.sub.2 SMe GaCH.sub.2 COEt H H CH.sub.2 SEt GaCH.sub.2 COEt H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 COEt H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 COEt H H CH.sub.2 CF.sub.3 GaCH.sub.2 COEt H H CH.sub.2 CN GaCH.sub.2 COEt H H CO.sub.2 Me GaCH.sub.2 COEt H H CO.sub.2 Et GaCH.sub.2 COEt H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 COEt H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 COEt H H COMe GaCH.sub.2 COEt H H COEt GaCH.sub.2 COEt H H CH.sub.2 COMe GaCH.sub.2 COEt H H CH.sub.2 COEt GaPh H H H GaPh H H Me GaPhCH.sub.2 H H H GbPhCH.sub.2 H H Me GbMe H H Ph GaMe H H PhCH.sub.2 GbMe H H CH.sub.2 CHCH.sub.2 GaMe H H CH.sub.2 CCH GaBu-t H H H Gb______________________________________
TABLE 8__________________________________________________________________________ ##STR151##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn__________________________________________________________________________H H H H H GaH H H H Me GaH H H H Et GaH H H H Pr-n GbH Me H H H GaH H Me H H GaH Me H H Me GbH Me Me H Me GbH H H Me Me GbMe H H H H GaMe H H H Me GaMe H H H Et GaMe H H H Pr-n GbMe Me H H H GaMe H Me H H GaMe Me H H Me GbMe Me Me H Me GbMe H H Me Me GbMe H H H CF.sub.3 GbMe H H H CH.sub.2 F GbMe H H H CH.sub.2 Cl GbMe H H H CH.sub.2 Br GbMe H H H CH.sub.2 I GbMe H H H CH.sub.2 OMe GbMe H H H CH.sub.2 OEt GbMe H H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GbMe H H H CH.sub.2 OCH.sub.2 CCH GbMe H H H CH.sub.2 SMe GbMe H H H CH.sub.2 SO.sub.2 Me GbMe H H H CH.sub.2 CN GbMe H H H CO.sub.2 Me GbMe H H H CO.sub.2 Et GbMe H H H COMe GbMe H H H COEt GbMe H H H CH.sub.2 CO.sub.2 Me GbMe H H H CH.sub.2 CO.sub.2 Et GbMe H H H CH.sub.2 COMe GbMe H H H CH.sub.2 COEt GbEt H H H H GaEt H H H Me GaEt H H H Et GaEt H H H Pr-n GbEt Me H H H GaEt H Me H H GaEt Me H H Me GbEt Me Me H Me GbEt H H Me Me GbEt H H H CF.sub.3 GbEt H H H CH.sub.2 F GbEt H H H CH.sub.2 Cl GbEt H H H CH.sub.2 Br GbEt H H H CH.sub.2 I GbEt H H H CH.sub.2 OMe GbEt H H H CH.sub.2 OEt GbEt H H H CH.sub.2 CN GbEt H H H COMe GbEt H H H COEt GbEt H H H CH.sub.2 CO.sub.2 Me GbEt H H H CH.sub.2 CO.sub.2 Et GbEt H H H CH.sub.2 COMe GbEt H H H CH.sub.2 COEt GbPr-n H H H H GaPr-n H H H Me GaPr-n H H H Et GaPr-n H H H Pr-n GbPr-n Me H H H GaPr-n H Me H H GaPr-n Me H H Me GbPr-n Me Me H Me GbPr-n H H Me Me GbPr-n H H H CF.sub.3 GbPr-n H H H CH.sub.2 F GbPr-n H H H CH.sub.2 Cl GbPr-n H H H CH.sub.2 Br GbPr-n H H H CH.sub.2 I GbPr-n H H H CH.sub.2 OMe GbPr-n H H H CH.sub.2 OEt GbPr-i H H H H GaPr-i H H H Me GaPr-i H H H Et GaPr-i H H H Pr-n GbPr-i Me H H H GaPr-i H Me H H GaPr-i Me H H Me GbPr-i Me Me H Me GbPr-i H H Me Me GbBu-n H H H H GaBu-n H H H Me GaBu-n H H H Et GaBu-n H H H Pr-n GbCH.sub.2 CHCH.sub.2 H H H H GaCH.sub.2 CHCH.sub.2 H H H Me GaCH.sub.2 CHCH.sub.2 H H H Et GaCH.sub.2 CHCH.sub.2 H H H Pr-n GbCH.sub.2 CHCH.sub.2 Me H H H GaCH.sub.2 CHCH.sub.2 H Me H H GaCH.sub.2 CHCH.sub.2 Me H H Me GbCH.sub.2 CHCH.sub.2 Me Me H Me GbCH.sub.2 CHCH.sub.2 H H Me Me GbCH.sub.2 CCH H H H H GaCH.sub.2 CCH H H H Me GaCH.sub.2 CCH H H H Et GaCH.sub.2 CCH H H H Pr-n GbCH.sub.2 CCH Me H H H GaCH.sub.2 CCH H Me H H GaCH.sub.2 CCH Me H H Me GbCH.sub.2 CCH Me Me H Me GbCH.sub.2 CCH H H Me Me GbCH.sub.2 OMe H H H H GaCH.sub.2 OMe H H H Me GaCH.sub.2 OMe H H H Et GaCH.sub.2 OMe H H H Pr-n GbCH.sub.2 OMe Me H H H GaCH.sub.2 OMe H Me H H GaCH.sub.2 OMe Me H H Me GbCH.sub.2 OMe Me Me H Me GbCH.sub.2 OMe H H Me Me GbCH.sub.2 OMe H H H CF.sub.3 GbCH.sub.2 OMe H H H CH.sub.2 F GbCH.sub.2 OMe H H H CH.sub.2 Cl GbCH.sub.2 OMe H H H CH.sub.2 Br GbCH.sub.2 OMe H H H CH.sub.2 I GbCH.sub.2 OMe H H H CH.sub.2 OMe GbCH.sub.2 OMe H H H CH.sub.2 OEt GbCH.sub.2 OMe H H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GbCH.sub.2 OMe H H H CH.sub.2 OCH.sub.2 CCH GbCH.sub.2 OMe H H H CH.sub.2 SMe GbCH.sub.2 OMe H H H CH.sub.2 SO.sub.2 Me GbCH.sub.2 OMe H H H CH.sub.2 CN GbCH.sub.2 OMe H H H CO.sub.2 Me GbCH.sub.2 OMe H H H CO.sub.2 Et GbCH.sub.2 OMe H H H COMe GbCH.sub.2 OMe H H H COEt GbCH.sub.2 OMe H H H CH.sub.2 CO.sub.2 Me GbCH.sub.2 OMe H H H CH.sub.2 CO.sub.2 Et GbCH.sub.2 OMe H H H CH.sub.2 COMe GbCH.sub.2 OMe H H H CH.sub.2 COEt GbCH.sub.2 OEt H H H H GaCH.sub.2 OEt H H H Me GaCH.sub.2 OEt H H H Et GaCH.sub.2 OEt H H H Pr-n GbCH.sub.2 OEt Me H H H GaCH.sub.2 OEt H Me H H GaCH.sub.2 OEt Me H H Me GbCH.sub.2 OEt Me Me H Me GbCH.sub.2 OEt H H Me Me GbCH.sub.2 OEt H H H CF.sub.3 GbCH.sub.2 OEt H H H CH.sub.2 F GbCH.sub.2 OEt H H H CH.sub.2 Cl GbCH.sub.2 OEt H H H CH.sub.2 Br GbCH.sub.2 OEt H H H CH.sub.2 I GbCH.sub.2 OEt H H H CH.sub.2 OMe GbCH.sub.2 OEt H H H CH.sub.2 OEt GbCH.sub.2 OEt H H H CH.sub.2 CN GbCH.sub.2 OEt H H H COMe GbCH.sub.2 OEt H H H COEt GbCH.sub.2 OEt H H H CH.sub.2 CO.sub.2 Me GbCH.sub.2 OEt H H H CH.sub.2 CO.sub.2 Et GbCH.sub.2 OEt H H H CH.sub.2 COMe GbCH.sub.2 OEt H H H CH.sub.2 COEt GbCH.sub.2 CH.sub.2 OMe H H H H GaCH.sub.2 CH.sub.2 OMe H H H Me GaCH.sub.2 CH.sub.2 OMe H H H Et GaCH.sub.2 CH.sub.2 OMe H H H Pr-n GbCH.sub.2 CH.sub.2 OMe Me H H H GaCH.sub.2 CH.sub.2 OMe H Me H H GaCH.sub.2 CH.sub.2 OMe Me H H Me GbCH.sub.2 CH.sub.2 OMe Me Me H Me GbCH.sub.2 CH.sub.2 OMe H H Me Me GbCH.sub.2 CH.sub.2 OMe H H H CF.sub.3 GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 F GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 Cl GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 I GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 OMe GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 OEt GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 CN GbCH.sub.2 CH.sub.2 OMe H H H COMe GbCH.sub.2 CH.sub.2 OMe H H H COEt GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 CO.sub.2 Me GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 CO.sub.2 Et GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 COMe GbCH.sub.2 CH.sub.2 OMe H H H CH.sub.2 COEt GbCH.sub.2 CH.sub.2 OEt H H H H GaCH.sub.2 CH.sub.2 OEt H H H Me GaCH.sub.2 CH.sub.2 OEt H H H Et GaCH.sub.2 CH.sub.2 OEt H H H Pr-n GbCH.sub.2 CH.sub.2 OEt Me H H H GaCH.sub.2 CH.sub.2 OEt H Me H H GaCH.sub.2 CH.sub.2 OEt Me H H Me GbCH.sub.2 CH.sub.2 OEt Me Me H Me GbCH.sub.2 CH.sub.2 OEt H H Me Me GbCH.sub.2 CH.sub.2 OEt H H H CF.sub.3 GbCH.sub.2 CH.sub.2 OEt H H H CH.sub.2 F GbCH.sub.2 CH.sub.2 OEt H H H CH.sub.2 Cl GbCH.sub.2 CH.sub.2 OEt H H H CH.sub.2 Br GbCH.sub.2 CH.sub.2 OEt H H H CH.sub.2 I GbCH.sub.2 CH.sub.2 OEt H H H CH.sub.2 OMe GbCH.sub.2 CH.sub.2 OEt H H H CH.sub.2 OEt GbCH(CH.sub.3)CH.sub.2 OMe H H H H GaCH(CH.sub.3)CH.sub.2 OMe H H H Me GaCH(CH.sub.3)CH.sub.2 OMe H H H Et GaCH(CH.sub.3)CH.sub.2 OMe H H H Pr-n GbCH(CH.sub.3)CH.sub.2 OMe Me H H H GaCH(CH.sub.3)CH.sub.2 OMe H Me H H GaCH(CH.sub.3)CH.sub.2 OMe Me H H Me GbCH(CH.sub.3)CH.sub.2 OMe Me Me H Me GbCH(CH.sub.3)CH.sub.2 OMe H H Me Me GbCH(CH.sub.3)CH.sub.2 OMe H H H CF.sub.3 GbCH(CH.sub.3)CH.sub.2 OMe H H H CH.sub.2 F GbCH(CH.sub.3)CH.sub.2 OMe H H H CH.sub.2 Cl GbCH(CH.sub.3)CH.sub.2 OMe H H H CH.sub.2 Br GbCH(CH.sub.3)CH.sub.2 OMe H H H CH.sub.2 I GbCH(CH.sub.3)CH.sub.2 OMe H H H CH.sub.2 OMe GbCH(CH.sub.3)CH.sub.2 OMe H H H CH.sub.2 OEt GbCH(CH.sub.3)CH.sub.2 OEt H H H H GaCH(CH.sub.3)CH.sub.2 OEt H H H Me GaCH(CH.sub.3)CH.sub.2 OEt H H H Et GaCH(CH.sub.3)CH.sub.2 OEt H H H Pr-N GbCH(CH.sub.3)CH.sub.2 OEt Me H H H GaCH(CH.sub.3)CH.sub.2 OEt H Me H H GaCH(CH.sub.3)CH.sub.2 OEt Me H H Me GbCH(CH.sub.3)CH.sub.2 OEt Me Me H Me GbCH(CH.sub.3)CH.sub.2 OEt H H Me Me GbCH.sub.2 OCHF.sub.2 H H H H GaCH.sub.2 OCHF.sub.2 H H H Me GaCH.sub.2 OCHF.sub.2 H H H Et GaCH.sub.2 OCHF.sub.2 H H H Pr-n GbCH.sub.2 OCHF.sub.2 Me H H H GaCH.sub.2 OCHF.sub.2 H Me H H GaCH.sub.2 OCHF.sub.2 Me H H Me GbCH.sub.2 OCHF.sub.2 Me Me H Me GbCH.sub.2 OCHF.sub.2 H H Me Me GbCH.sub.2 SMe H H H H GaCH.sub.2 SMe H H H Me GaCH.sub.2 SMe H H H Et GaCH.sub.2 SMe H H H Pr-n GbCH.sub.2 SMe Me H H H GaCH.sub.2 SMe H Me H H GaCH.sub.2 SMe Me H H Me GbCH.sub.2 SMe Me Me H Me GbCH.sub.2 SMe H H Me Me GbCH.sub.2 SMe H H H CF.sub.3 GbCH.sub.2 SMe H H H CH.sub.2 F GbCH.sub.2 SMe H H H CH.sub.2 Cl GbCH.sub.2 SMe H H H CH.sub.2 Br GbCH.sub.2 SMe H H H CH.sub.2 I GbCH.sub.2 SMe H H H CH.sub.2 OMe GbCH.sub.2 SMe H H H CH.sub.2 OEt GbCH.sub.2 SMe H H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GbCH.sub.2 SMe H H H CH.sub.2 OCH.sub.2 CCH GbCH.sub.2 SMe H H H CH.sub.2 SMe GbCH.sub.2 SMe H H H CH.sub.2 SO.sub.2 Me GbCH.sub.2 SMe H H H CH.sub.2 CN GbCH.sub.2 SMe H H H CO.sub.2 Me GbCH.sub.2 SMe H H H CO.sub.2 Et GbCH.sub.2 SMe H H H COMe GbCH.sub.2 SMe H H H COEt GbCH.sub.2 SMe H H H CH.sub.2 CO.sub.2 Me GbCH.sub.2 SMe H H H CH.sub.2 CO.sub.2 Et GbCH.sub.2 SMe H H H CH.sub.2 COMe GbCH.sub.2 SMe H H H CH.sub.2 COEt GbCH.sub.2 SEt H H H H GaCH.sub.2 SEt H H H Me GaCH.sub.2 SEt H H H Et GaCH.sub.2 SEt H H H Pr-n GbCH.sub.2 SEt Me H H H GaCH.sub.2 SEt H Me H H GaCH.sub.2 SEt Me H H Me GbCH.sub.2 SEt Me Me H Me GbCH.sub.2 SEt H H Me Me GbCH.sub.2 SEt H H H CF.sub.3 GbCH.sub.2 SEt H H H CH.sub.2 F GbCH.sub.2 SEt H H H CH.sub.2 Cl GbCH.sub.2 SEt H H H CH.sub.2 Br GbCH.sub.2 SEt H H H CH.sub.2 I GbCH.sub.2 SEt H H H CH.sub.2 OMe GbCH.sub.2 SEt H H H CH.sub.2 OEt GbCH.sub.2 SO.sub.2 Me H H H H GaCH.sub.2 SO.sub.2 Me H H H Me GaCH.sub.2 SO.sub.2 Me H H H Et GaCH.sub.2 SO.sub.2 Me H H H Pr-n GbCH.sub.2 SO.sub.2 Me Me H H H GaCH.sub.2 SO.sub.2 Me H Me H H GaCH.sub.2 SO.sub.2 Me Me H H Me GbCH.sub.2 SO.sub.2 Me Me Me H Me GbCH.sub.2 SO.sub.2 Me H H Me Me GbCH.sub.2 SO.sub.2 Me H H H CF.sub.3 GbCH.sub.2 SO.sub.2 Me H H H CH.sub.2 F GbCH.sub.2 SO.sub.2 Me H H H CH.sub.2 Cl GbCH.sub.2 SO.sub.2 Me H H H CH.sub.2 Br GbCH.sub.2 SO.sub.2 Me H H H CH.sub.2 I GbCH.sub.2 SO.sub.2 Me H H H CH.sub.2 OMe GbCH.sub.2 SO.sub.2 Me H H H CH.sub.2 OEt GbCH.sub.2 SO.sub.2 Et H H H H GaCH.sub.2 SO.sub.2 Et H H H Me GaCH.sub.2 SO.sub.2 Et H H H Et GaCH.sub.2 SO.sub.2 Et H H H Pr-n GbCH.sub.2 SO.sub.2 Et Me H H H GaCH.sub.2 SO.sub.2 Et H Me H H GaCH.sub.2 SO.sub.2 Et Me H H Me GbCH.sub.2 SO.sub.2 Et Me Me H Me GbCH.sub.2 SO.sub.2 Et H H Me Me GbCH.sub.2 F H H H H GaCH.sub.2 F H H H Me GaCH.sub.2 F H H H Et GaCH.sub.2 F H H H Pr-n GbCH.sub.2 F Me H H H GaCH.sub.2 F H Me H H GaCH.sub.2 F Me H H Me GbCH.sub.2 F Me Me H Me GbCH.sub.2 F H H Me Me GbCH.sub.2 F H H H CF.sub.3 GbCH.sub.2 F H H H CH.sub.2 F GbCH.sub.2 F H H H CH.sub.2 Cl GbCH.sub.2 F H H H CH.sub.2 Br GbCH.sub.2 F H H H CH.sub.2 I GbCH.sub.2 F H H H CH.sub.2 OMe GbCH.sub.2 F H H H CH.sub.2 OEt GbCH.sub.2 Cl H H H H GaCH.sub.2 Cl H H H Me GaCH.sub.2 Cl H H H Et GaCH.sub.2 Cl H H H Pr-n GbCH.sub.2 Cl Me H H H GaCH.sub.2 Cl H Me H H GaCH.sub.2 Cl Me H H Me GbCH.sub.2 Cl Me Me H Me GbCH.sub.2 Cl H H Me Me GbCH.sub.2 Cl H H H CF.sub.3 GbCH.sub.2 Cl H H H CH.sub.2 F GbCH.sub.2 Cl H H H CH.sub.2 Cl GbCH.sub.2 Cl H H H CH.sub.2 Br GbCH.sub.2 Cl H H H CH.sub.2 I GbCH.sub.2 Cl H H H CH.sub.2 OMe GbCH.sub.2 Cl H H H CH.sub.2 OEt GbCH.sub.2 Br H H H H GaCH.sub.2 Br H H H Me GaCH.sub.2 Br H H H Et GaCH.sub.2 Br H H H Pr-n GbCH.sub.2 Br Me H H H GaCH.sub.2 Br H Me H H GaCH.sub.2 Br Me H H Me GbCH.sub.2 Br Me Me H Me GbCH.sub.2 Br H H Me Me GbCH.sub.2 Br H H H CF.sub.3 GbCH.sub.2 Br H H H CH.sub.2 F GbCH.sub.2 Br H H H CH.sub.2 Cl GbCH.sub.2 Br H H H CH.sub.2 Br GbCH.sub.2 Br H H H CH.sub.2 I GbCH.sub.2 Br H H H CH.sub.2 OMe GbCH.sub.2 Br H H H CH.sub.2 OEt GbCH.sub.2 I H H H H GaCH.sub.2 I H H H Me GaCH.sub.2 I H H H Et GaCH.sub.2 I H H H Pr-n GbCH.sub.2 I Me H H H GaCH.sub.2 I H Me H H GaCH.sub.2 I Me H H Me GbCH.sub.2 I Me Me H Me GbCH.sub.2 I H H Me Me GbCH.sub.2 I H H H CF.sub.3 GbCH.sub.2 I H H H CH.sub.2 F GbCH.sub.2 I H H H CH.sub.2 Cl GbCH.sub.2 I H H H CH.sub.2 Br GbCH.sub.2 I H H H CH.sub.2 I GbCH.sub.2 I H H H CH.sub.2 OMe GbCH.sub.2 I H H H CH.sub.2 OEt GbCH.sub.2 CH.sub.2 F H H H H GaCH.sub.2 CH.sub.2 F H H H Me GaCH.sub.2 CH.sub.2 F H H H Et GaCH.sub.2 CH.sub.2 F H H H Pr-n GbCH.sub.2 CH.sub.2 F Me H H H GaCH.sub.2 CH.sub.2 F H Me H H GaCH.sub.2 CH.sub.2 F Me H H Me GbCH.sub.2 CH.sub.2 F Me Me H Me GbCH.sub.2 CH.sub.2 F H H Me Me GbCH.sub.2 CH.sub.2 Cl H H H H GaCH.sub.2 CH.sub.2 Cl H H H Me GaCH.sub.2 CH.sub.2 Cl H H H Et GaCH.sub.2 CH.sub.2 Cl H H H Pr-n GbCH.sub.2 CH.sub.2 Cl Me H H H GaCH.sub.2 CH.sub.2 Cl H Me H H GaCH.sub.2 CH.sub.2 Cl Me H H Me GbCH.sub.2 CH.sub.2 Cl Me Me H Me GbCH.sub.2 CH.sub.2 Cl H H Me Me GbCH.sub.2 CH.sub.2 Br H H H H GaCH.sub.2 CH.sub.2 Br H H H Me GaCH.sub.2 CH.sub.2 Br H H H Et GaCH.sub.2 CH.sub.2 Br H H H Pr-n GbCH.sub.2 CH.sub.2 Br Me H H H GaCH.sub.2 CH.sub.2 Br H Me H H GaCH.sub.2 CH.sub.2 Br Me H H Me GbCH.sub.2 CH.sub.2 Br Me Me H Me GbCH.sub.2 CH.sub.2 Br H H Me Me GbCH.sub.2 CH.sub.2 I H H H H GaCH.sub.2 CH.sub.2 I H H H Me GaCH.sub.2 CH.sub.2 I H H H Et GaCH.sub.2 CH.sub.2 I H H H Pr-n GbCH.sub.2 CH.sub.2 I Me H H H GaCH.sub.2 CH.sub.2 I H Me H H GaCH.sub.2 CH.sub.2 I Me H H Me GbCH.sub.2 CH.sub.2 I Me Me H Me GbCH.sub.2 CH.sub.2 I H H Me Me GbCH(CH.sub.3)CH.sub.2 F H H H H GaCH(CH.sub.3)CH.sub.2 F H H H Me GaCH(CH.sub.3)CH.sub.2 F H H H Et GaCH(CH.sub.3)CH.sub.2 F H H H Pr-n GbCH(CH.sub.3)CH.sub.2 F Me H H H GaCH(CH.sub.3)CH.sub.2 F H Me H H GaCH(CH.sub.3)CH.sub.2 F Me H H Me GbCH(CH.sub.3)CH.sub.2 F Me Me H Me GbCH(CH.sub.3)CH.sub.2 F H H Me Me GbCH(CH.sub.3)CH.sub.2 Cl H H H H GaCH(CH.sub.3)CH.sub.2 Cl H H H Me GaCH(CH.sub.3)CH.sub.2 Cl H H H Et GaCH(CH.sub.3)CH.sub.2 Cl H H H Pr-n GbCH(CH.sub.3)CH.sub.2 Cl Me H H H GaCH(CH.sub.3)CH.sub.2 Cl H Me H H GaCH(CH.sub.3)CH.sub.2 Cl Me H H Me GbCH(CH.sub.3)CH.sub.2 Cl Me Me H Me GbCH(CH.sub.3)CH.sub.2 Cl H H Me Me GbCH(CH.sub.3)CH.sub.2 Br H H H H GaCH(CH.sub.3)CH.sub.2 Br H H H Me GaCH(CH.sub.3)CH.sub.2 Br H H H Et GaCH(CH.sub.3)CH.sub.2 Br H H H Pr-n GbCH(CH.sub.3)CH.sub.2 Br Me H H H GaCH(CH.sub.3)CH.sub.2 Br H Me H H GaCH(CH.sub.3)CH.sub.2 Br Me H H Me GbCH(CH.sub.3)CH.sub.2 Br Me Me H Me GbCH(CH.sub.3)CH.sub.2 Br H H Me Me GbCH(CH.sub.3)CH.sub.2 I H H H H GaCH(CH.sub.3)CH.sub.2 I H H H Me GaCH(CH.sub.3)CH.sub.2 I H H H Et GaCH(CH.sub.3)CH.sub.2 I H H H Pr-n GbCH(CH.sub.3)CH.sub.2 I Me H H H GaCH(CH.sub.3)CH.sub.2 I H Me H H GaCH(CH.sub.3)CH.sub.2 I Me H H Me GbCH(CH.sub.3)CH.sub.2 I Me Me H Me GbCH(CH.sub.3)CH.sub.2 I H H Me Me GbCH.sub.2 CF.sub.3 H H H H GaCH.sub.2 CF.sub.3 H H H Me GaCH.sub.2 CF.sub.3 H H H Et GaCH.sub.2 CF.sub.3 H H H Pr-n GbCH.sub.2 CF.sub.3 Me H H H GaCH.sub.2 CF.sub.3 H Me H H GaCH.sub.2 CF.sub.3 Me H H Me GbCH.sub.2 CF.sub.3 Me Me H Me GbCH.sub.2 CF.sub.3 H H Me Me GbCH.sub.2 CF.sub.3 H H H CF.sub.3 GbCH.sub.2 CF.sub.3 H H H CH.sub.2 F GbCH.sub.2 CF.sub.3 H H H CH.sub.2 Cl GbCH.sub.2 CF.sub.3 H H H CH.sub.2 Br GbCH.sub.2 CF.sub.3 H H H CH.sub.2 I GbCH.sub.2 CF.sub.3 H H H CH.sub.2 OMe GbCH.sub.2 CF.sub.3 H H H CH.sub.2 OEt GbCH.sub.2 CN H H H H GaCH.sub.2 CN H H H Me GaCH.sub.2 CN H H H Et GaCH.sub.2 CN H H H Pr-n GbCH.sub.2 CN Me H H H GaCH.sub.2 CN H Me H H GaCH.sub.2 CN Me H H Me GbCH.sub.2 CN Me Me H Me GbCH.sub.2 CN H H Me Me GbCH.sub.2 CN H H H CF.sub.3 GbCH.sub.2 CN H H H CH.sub.2 F GbCH.sub.2 CN H H H CH.sub.2 Cl GbCH.sub.2 CN H H H CH.sub.2 Br GbCH.sub.2 CN H H H CH.sub.2 I GbCH.sub.2 CN H H H CH.sub.2 OMe GbCH.sub.2 CN H H H CH.sub.2 OEt GbCH.sub.2 CO.sub.2 Me H H H H GaCH.sub.2 CO.sub.2 Me H H H Me GaCH.sub.2 CO.sub.2 Me H H H Et GaCH.sub.2 CO.sub.2 Me H H H Pr-n GbCH.sub.2 CO.sub.2 Me Me H H H GaCH.sub.2 CO.sub.2 Me H Me H H GaCH.sub.2 CO.sub.2 Me Me H H Me GbCH.sub.2 CO.sub.2 Me Me Me H Me GbCH.sub.2 CO.sub.2 Me H H Me Me GbCH.sub.2 CO.sub.2 Me H H H CF.sub.3 GbCH.sub.2 CO.sub.2 Me H H H CH.sub.2 F GbCH.sub.2 CO.sub.2 Me H H H CH.sub.2 Cl GbCH.sub.2 CO.sub.2 Me H H H CH.sub.2 Br GbCH.sub.2 CO.sub.2 Me H H H CH.sub.2 I GbCH.sub.2 CO.sub.2 Me H H H CH.sub.2 OMe GbCH.sub.2 CO.sub.2 Me H H H CH.sub.2 OEt GbCH.sub.2 CO.sub.2 Et H H H H GaCH.sub.2 CO.sub.2 Et H H H Me GaCH.sub.2 CO.sub.2 Et H H H Et GaCH.sub.2 CO.sub.2 Et H H H Pr-n GbCH.sub.2 CO.sub.2 Et Me H H H GaCH.sub.2 CO.sub.2 Et H Me H H GaCH.sub.2 CO.sub.2 Et Me H H Me GbCH.sub.2 CO.sub.2 Et Me Me H Me GbCH.sub.2 CO.sub.2 Et H H Me Me GbCH.sub.2 CO.sub.2 Pr-n H H H H GaCH.sub.2 CO.sub.2 Pr-n H H H Me GaCH.sub.2 CO.sub.2 Pr-n H H H Et GaCH.sub.2 CO.sub.2 Pr-n H H H Pr-n GbCH.sub.2 CO.sub.2 Pr-n Me H H H GaCH.sub.2 CO.sub.2 Pr-n H Me H H GaCH.sub.2 CO.sub.2 Pr-n Me H H Me GbCH.sub.2 CO.sub.2 Pr-n Me Me H Me GbCH.sub.2 CO.sub.2 Pr-n H H Me Me GbCH.sub.2 COMe H H H H GaCH.sub.2 COMe H H H Me GaCH.sub.2 COMe H H H Et GaCH.sub.2 COMe H H H Pr-n GbCH.sub.2 COMe Me H H H GaCH.sub.2 COMe H Me H H GaCH.sub.2 COMe Me H H Me GbCH.sub.2 COMe Me Me H Me GbCH.sub.2 COMe H H Me Me GbCH.sub.2 COMe H H H CF.sub.3 GbCH.sub.2 COMe H H H CH.sub.2 F GbCH.sub.2 COMe H H H CH.sub.2 Cl GbCH.sub.2 COMe H H H CH.sub.2 Br GbCH.sub.2 COMe H H H CH.sub.2 I GbCH.sub.2 COMe H H H CH.sub.2 OMe GbCH.sub.2 COMe H H H CH.sub.2 OEt GbCH.sub.2 COEt H H H H GaCH.sub.2 COEt H H H Me GaCH.sub.2 COEt H H H Et GaCH.sub.2 COEt H H H Pr-n GbCH.sub.2 COEt Me H H H GaCH.sub.2 COEt H Me H H GaCH.sub.2 COEt Me H H Me GbCH.sub.2 COEt Me Me H Me GbCH.sub.2 COEt H H Me Me GbCH.sub.2 COEt H H H CF.sub.3 GbCH.sub.2 COEt H H H CH.sub.2 F GbCH.sub.2 COEt H H H CH.sub.2 Cl GbCH.sub.2 COEt H H H CH.sub.2 Br GbCH.sub. 2 COEt H H H CH.sub.2 I GbCH.sub.2 COEt H H H CH.sub.2 OMe GbCH.sub.2 COEt H H H CH.sub.2 OEt GbPh H H H H GaPhCH.sub.2 H H H H GbPh H H H Me GaPhCH.sub.2 H H H Me GbMe H H H Ph GaMe H H H PhCH.sub.2 GbMe H H H Cl GbMe H H H CH.sub.2CHCH.sub.2 GaMe H H H CHCCH.sub.2 Ga__________________________________________________________________________
TABLE 9______________________________________ ##STR152##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________Me H H H GaMe H H Me GaMe H H Et GbMe H H Pr-n GbMe H H Pr-i GbMe H H Bu-n GcMe Me H H GaMe Et H H GbMe Me H Me GbMe Me H Et GbMe H Me Me GaMe H Me Et GbMe H H F GaMe H H Cl GaMe H H Br GbMe H H I GbMe H H CF.sub.3 GaMe H H CH.sub.2 F GaMe H H CH.sub.2 Cl GaMe H H CH.sub.2 Br GbMe H H CH.sub.2 I GbMe H H CH.sub.2 CH.sub.2 F GaMe H H CH.sub.2 CH.sub.2 Cl GaMe H H CH.sub.2 CH.sub.2 Br GbMe H H CH.sub.2 CH.sub.2 I GbMe H H CH(CH.sub.3)CH.sub.2 F GaMe H H CH(CH.sub.3)CH.sub.2 Cl GaMe H H CH(CH.sub.3)CH.sub.2 Br GbMe H H CH(CH.sub.3)CH.sub.2 I GbMe H H CH.sub.2 OMe GaMe H H CH.sub.2 OEt GaMe H H CH.sub.2 CH.sub.2 OMe GaMe H H CH.sub.2 CH.sub.2 OEt GaMe H H CH(CH.sub.3)CH.sub.2 OMe GbMe H H CH(CH.sub.3)CH.sub.2 OEt GbMe H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaMe H H CH.sub.2 OCH.sub.2 CCH GaMe H H CH.sub.2 OCHF.sub.2 GaMe H H CH.sub.2 OCF.sub.3 GaMe H H CH.sub.2 SMe GaMe H H CH.sub.2 SEt GaMe H H CH.sub.2 SO.sub.2 Me GaMe H H CH.sub.2 SO.sub.2 Et GaMe H H CH.sub.2 CF.sub.3 GaMe H H CH.sub.2 CN GaMe H H CO.sub.2 Me GaMe H H CO.sub.2 Et GaMe H H CO.sub.2 Pr-n GbMe H H CH.sub.2 CO.sub.2 Me GaMe H H CH.sub.2 CO.sub.2 Et GaMe H H CH.sub.2 CO.sub.2 Pr-n GbMe H H COMe GaMe H H COEt GaMe H H COPr-n GbMe H H CH.sub.2 COMe GaMe H H CH.sub.2 COEt GaEt H H H GaEt H H Me GaEt H H Et GbEt H H Pr-n GbEt H H Pr-i GbEt H H Bu-n GcEt Me H H GaEt Et H H GbEt Me H Me GbEt Me H Et GbEt H Me Me GaEt H Me Et GbEt H H F GaEt H H Cl GaEt H H Br GbEt H H I GbEt H H CF.sub.3 GaEt H H CH.sub.2 F GaEt H H CH.sub.2 Cl GaEt H H CH.sub.2 Br GbEt H H CH.sub.2 I GbEt H H CH.sub.2 CH.sub.2 F GaEt H H CH.sub.2 CH.sub.2 Cl GaEt H H CH.sub.2 CH.sub.2 Br GbEt H H CH.sub.2 CH.sub.2 I GbEt H H CH(CH.sub.3)CH.sub.2 F GaEt H H CH(CH.sub.3)CH.sub.2 Cl GaEt H H CH(CH.sub.3)CH.sub.2 Br GbEt H H CH(CH.sub.3)CH.sub.2 I GbEt H H CH.sub.2 OMe GaEt H H CH.sub.2 OEt GaEt H H CH.sub.2 CH.sub.2 OMe GaEt H H CH.sub.2 CH.sub.2 OEt GaEt H H CH(CH.sub.3)CH.sub.2 OMe GbEt H H CH(CH.sub.3)CH.sub.2 OEt GbEt H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaEt H H CH.sub.2 OCH.sub.2 CCH GaEt H H CH.sub.2 OCHF.sub.2 GaEt H H CH.sub.2 OCF.sub.3 GaEt H H CH.sub.2 SMe GaEt H H CH.sub.2 SEt GaEt H H CH.sub.2 SO.sub.2 Me GaEt H H CH.sub.2 SO.sub.2 Et GaEt H H CH.sub.2 CF.sub.3 GaEt H H CH.sub.2 CN GaEt H H CO.sub.2 Me GaEt H H CO.sub.2 Et GaEt H H CO.sub.2 Pr-n GbEt H H CH.sub.2 CO.sub.2 Me GaEt H H CH.sub.2 CO.sub.2 Et GaEt H H CH.sub.2 CO.sub.2 Pr-n GbEt H H COMe GaEt H H COEt GaEt H H COPr-n GbEt H H CH.sub.2 COMe GaEt H H CH.sub.2 COEt GaPr-n H H H GaPr-n H H Me GbPr-n H H Et GbPr-n Me H H GaPr-n Et H H GbPr-n Me H Me GbPr-n Me H Et GbPr-n H Me Me GaPr-n H Me Et GbPr-n H H CF.sub.3 GaPr-n H H CH.sub.2 F GaPr-n H H CH.sub.2 Cl GaPr-n H H CH.sub.2 Br GbPr-n H H CH.sub.2 I GbPr-n H H CH.sub.2 OMe GaPr-n H H CH.sub.2 OEt GaPr-n H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaPr-n H H CH.sub.2 OCH.sub.2 C CH GaPr-n H H CH.sub.2 OCHF.sub.2 GaPr-n H H CH.sub.2 OCF.sub.3 GaPr-n H H CH.sub.2 SMe GaPr-n H H CH.sub.2 SEt GaPr-n H H CH.sub.2 SO.sub.2 Me GaPr-n H H CH.sub.2 SO.sub.2 Et GaPr-n H H CH.sub.2 CF.sub.3 GaPr-n H H CH.sub.2 CN GaPr-n H H CO.sub.2 Me GaPr-n H H CO.sub.2 Et GaPr-n H H CH.sub.2 CO.sub.2 Me GaPr-n H H CH.sub.2 CO.sub.2 Et GaPr-n H H COMe GaPr-n H H COEt GaPr-n H H CH.sub.2 COMe GaPr-n H H CH.sub.2 COEt GaPr-i H H H GaPr-i H H Me GbPr-i H H Et GbPr-i Me H H GaPr-i Et H H GbPr-i Me H Me GbPr-i Me H Et GbPr-i H Me Me GaPr-i H Me Et GbPr-i H H CF.sub.3 GaPr-i H H CH.sub.2 F GaPr-i H H CH.sub.2 Cl GaPr-i H H CH.sub.2 Br GbPr-i H H CH.sub.2 I GbPr-i H H CH.sub.2 OMe GaPr-i H H CH.sub.2 OEt GaPr-i H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaPr-i H H CH.sub.2 OCH.sub.2 CCH GaPr-i H H CH.sub.2 OCHF.sub.2 GaPr-i H H CH.sub.2 OCF.sub.3 GaPr-i H H CH.sub.2 SMe GaPr-i H H CH.sub.2 SEt GaPr-i H H CH.sub.2 SO.sub.2 Me GaPr-i H H CH.sub.2 SO.sub.2 Et GaPr-i H H CH.sub.2 CF.sub.3 GaPr-i H H CH.sub.2 CN GaPr-i H H CO.sub.2 Me GaPr-i H H CO.sub.2 Et GaPr-i H H CH.sub.2 CO.sub.2 Me GaPr-i H H CH.sub.2 CO.sub.2 Et GaPr-i H H COMe GaPr-i H H COEt GaPr-i H H CH.sub.2 COMe GaPr-i H H CH.sub.2 COEt GaBu-n H H H GaBu-n H H Me GbBu-n Me H H GaBu-n Me H Me GbBu-n H Me Me GaBu-n H H CF.sub.3 GaBu-n H H CH.sub.2 F GaBu-n H H CH.sub.2 Cl GaBu-n H H CH.sub.2 Br GbBu-n H H CH.sub.2 I GbBu-n H H CH.sub.2 OMe GaBu-n H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaBu-n H H CH.sub.2 OCH.sub.2 CCH GaBu-n H H CH.sub.2 OCHF.sub.2 GaBu-n H H CH.sub.2 OCF.sub.3 GaBu-n H H CH.sub.2 SMe GaBu-n H H CH.sub.2 SO.sub.2 Me GaBu-n H H CH.sub.2 CF.sub.3 GaBu-n H H CH.sub.2 CN GaBu-n H H CO.sub.2 Me GaBu-n H H CH.sub.2 CO.sub.2 Me GaBu-n H H COMe GaBu-n H H CH.sub.2 COMe GaCH.sub.2 CHCH.sub.2 H H H GaCH.sub.2 CHCH.sub.2 H H Me GbCH.sub.2 CHCH.sub.2 H H Et GbCH.sub.2 CHCH.sub.2 Me H H GaCH.sub.2 CHCH.sub.2 Et H H GbCH.sub.2 CHCH.sub.2 Me H Me GbCH.sub.2 CHCH.sub.2 Me H Et GbCH.sub.2 CHCH.sub.2 H Me Me GaCH.sub.2 CHCH.sub.2 H Me Et GbCH.sub.2 CHCH.sub.2 H H CF.sub.3 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 F GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 Cl GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 Br GbCH.sub.2 CHCH.sub.2 H H CH.sub.2 I GbCH.sub.2 CHCH.sub.2 H H CH.sub.2 OMe GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OEt GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SMe GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SEt GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CF.sub.3 GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CN GaCH.sub.2 CHCH.sub.2 H H CO.sub.2 Me GaCH.sub.2 CHCH.sub.2 H H CO.sub.2 Et GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CHCH.sub.2 H H COMe GaCH.sub.2 CHCH.sub.2 H H COEt GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 COMe GaCH.sub.2 CHCH.sub.2 H H CH.sub.2 COEt GaCH.sub.2 CCH H H H GaCH.sub.2 CCH H H Me GbCH.sub.2 CCH H H Et GbCH.sub.2 CCH Me H H GaCH.sub.2 CCH Et H H GbCH.sub.2 CCH Me H Me GbCH.sub.2 CCH Me H Et GbCH.sub.2 CCH H Me Me GaCH.sub.2 CCH H H F GaCH.sub.2 CCH H Me Et GbCH.sub.2 CCH H H CF.sub.3 GaCH.sub.2 CCH H H CH.sub.2 F GaCH.sub.2 CCH H H CH.sub.2 Cl GaCH.sub.2 CCH H H CH.sub.2 Br GbCH.sub.2 CCH H H CH.sub.2 I GbCH.sub.2 CCH H H CH.sub.2 OMe GaCH.sub.2 CCH H H CH.sub.2 OEt GaCH.sub.2 CCH H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GaCH.sub.2 CCH H H CH.sub.2 OCH.sub.2 CCH GaCH.sub.2 CCH H H CH.sub.2 OCHF.sub.2 GaCH.sub.2 CCH H H CH.sub.2 OCF.sub.3 GaCH.sub.2 CCH H H CH.sub.2 SMe GaCH.sub.2 CCH H H CH.sub.2 SEt GaCH.sub.2 CCH H H CH.sub.2 SO.sub.2 Me GaCH.sub.2 CCH H H CH.sub.2 SO.sub.2 Et GaCH.sub.2 C CH H H CH.sub.2 CF.sub.3 GaCH.sub.2 CCH H H CH.sub.2 CN GaCH.sub.2 CCH H H CO.sub.2 Me GaCH.sub.2 CCH H H CO.sub.2 Et GaCH.sub.2 CCH H H CH.sub.2 CO.sub.2 Me GaCH.sub.2 CCH H H CH.sub.2 CO.sub.2 Et GaCH.sub.2 CCH H H COMe GaCH.sub.2 CCH H H COEt GaCH.sub.2 CCH H H CH.sub.2 COMe GaCH.sub.2 CCH H H CH.sub.2 COEt Ga______________________________________
TABLE 10______________________________________ ##STR153##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn______________________________________Me H H H H GaMe H H H Me GaMe H H H Et GaMe H H H Pr-n GbMe Me H H H GaMe H Me H H GaMe Me H H Me GbMe Me Me H Me GbMe H H Me Me GbMe H H H CF.sub.3 GbMe H H H CH.sub.2 F GbMe H H H CH.sub.2 Cl GbMe H H H CH.sub.2 Br GbMe H H H CH.sub.2 I GbMe H H H CH.sub.2 OMe GbMe H H H CH.sub.2 OEt GbMe H H H CH.sub.2 OCH.sub.2 CHCH.sub.2 GbMe H H H CH.sub.2 OCH.sub.2 CCH GbMe H H H CH.sub.2 SMe GbMe H H H CH.sub.2 SO.sub.2 Me GbMe H H H CH.sub.2 CN GbMe H H H CO.sub.2 Me GbMe H H H CO.sub.2 Et GbMe H H H COMe GbMe H H H COEt GbMe H H H CH.sub.2 CO.sub.2 Me GbMe H H H CH.sub.2 CO.sub.2 Et GbMe H H H CH.sub.2 COMe GbMe H H H CH.sub.2 COEt GbEt H H H H GaEt H H H Me GaEt H H H Et GaEt H H H Pr-n GbEt Me H H H GaEt H Me H H GaEt Me H H Me GbEt Me Me H Me GbEt H H Me Me GbEt H H H CF.sub.3 GbEt H H H CH.sub.2 F GbEt H H H CH.sub.2 Cl GbEt H H H CH.sub.2 Br GbEt H H H CH.sub.2 I GbEt H H H CH.sub.2 OMe GbEt H H H CH.sub.2 OEt GbEt H H H CH.sub.2 CN GbEt H H H COMe GbEt H H H COEt GbEt H H H CH.sub.2 CO.sub.2 Me GbEt H H H CH.sub.2 CO.sub.2 Et GbEt H H H CH.sub.2 COMe GbEt H H H CH.sub.2 COEt GbPr-n H H H H GaPr-n H H H Me GaPr-n H H H Et GaPr-n H H H Pr-n GbPr-n Me H H H GaPr-n H Me H H GaPr-n Me H H Me GbPr-n Me Me H Me GbPr-n H H Me Me GbPr-n H H H CF.sub.3 GbPr-n H H H CH.sub.2 F GbPr-n H H H CH.sub.2 Cl GbPr-n H H H CH.sub.2 Br GbPr-n H H H CH.sub.2 I GbPr-n H H H CH.sub.2 OMe GbPr-n H H H CH.sub.2 OEt GbPr-i H H H H GaPr-i H H H Me GaPr-i H H H Et GaPr-i H H H Pr-n GbPr-i Me H H H GaPr-i H Me H H GaPr-i Me H H Me GbPr-i Me Me H Me GbPr-i H H Me Me GbBu-n H H H H GaBu-n H H H Me GaBu-n H H H Et GaBu-n H H H Pr-n GbCH.sub.2 CHCH.sub.2 H H H H GaCH.sub.2 CHCH.sub.2 H H H Me GaCH.sub.2 CHCH.sub.2 H H H Et GaCH.sub.2 CHCH.sub.2 H H H Pr-n GbCH.sub.2 CHCH.sub.2 Me H H H GaCH.sub.2 CHCH.sub.2 H Me H H GaCH.sub.2 CHCH.sub.2 Me H H Me GbCH.sub.2 CHCH.sub.2 Me Me H Me GbCH.sub.2 CHCH.sub.2 H H Me Me GbCH.sub.2 CCH H H H H GaCH.sub.2 CCH H H H Me GaCH.sub.2 CCH H H H Et GaCH.sub.2 CCH H H H Pr-n GbCH.sub.2 CCH Me H H H GaCH.sub.2 CCH H Me H H GaCH.sub.2 CCH Me H H Me GbCH.sub.2 CCH Me Me H Me GbCH.sub.2 CCH H H Me Me Gb______________________________________
TABLE 11______________________________________ ##STR154##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________Me H H H GcMe H H Me GcMe H H Et GcMe Me H H GcMe Et H H GcMe Me H Me GcMe H Me Me GcEt H H H GcEt H H Me GcEt H H Et GcEt Me H H GcEt H Me Me Gc______________________________________
TABLE 12______________________________________ ##STR155##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn______________________________________Me H H H H GcMe H H H Me GcMe H H H Et GcMe Me H H H GcMe H Me H H GcMe H H Me Me GcMe Me H H Me GcEt H H H H GcEt H H Me Me GcEt Me H H H GcEt H H H Me Gc______________________________________
TABLE 13______________________________________ ##STR156##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________Me H H H GcMe H H Me GcMe H H Et GcMe Me H H GcMe Et H H GcMe Me H Me GcMe H Me Me GcEt H H H GcEt H H Me GcEt H H Et GcEt Me H H GcEt H Me Me Gc______________________________________
TABLE 14______________________________________ ##STR157##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn______________________________________Me H H H H GcMe H H H Me GcMe H H H Et GcMe Me H H H GcMe H Me H H GcMe H H Me Me GcMe Me H H Me GcEt H H H H GcEt H H H Me GcEt Me H H H GcEt H H Me Me Gc______________________________________
TABLE 1A______________________________________ ##STR158##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me G.sub.1Me Me Me G.sub.3Me Me Me G.sub.5Me Me Me G.sub.6Me Me Me G.sub.7Me Me Me G.sub.8Me Me Me G.sub.11Me Me Me G.sub.12Me Me Me G.sub.13Me Me Me G.sub.14Me Me Me G.sub.15Me Me Me G.sub.16Me Me Me G.sub.19Me Me Me G.sub.20Me Me Me G.sub.23Me Me Me G.sub.25Me Me Me G.sub.26Me Me Me G.sub.27Me Me Me G.sub.29Me Me Me G.sub.31Me Me Me G.sub.34Me Me Me G.sub.36Me Me Me G.sub.39Me Me Me G.sub.41Me Me Me G.sub.42Me Me Me G.sub.44Me Me Me G.sub.99Me Me Me G.sub.100Me Me Me G.sub.103Me Me Me G.sub.116Me Me Me G.sub. 117Me Me Me G.sub.120Me Me Me G.sub.121Me Me Me G.sub.122Me Me Me G.sub.123Me Me Me G.sub.124Me Me Me G.sub.125Me Me Me G.sub.126Me Me Me G.sub.129Me Me Me G.sub.132Me Me Me G.sub.144Me Me Me G.sub.180Me Me Me G.sub.181Me Me Me G.sub.189Me Me Me G.sub.190Me Me Me G.sub.192Me Me Me G.sub.193Me Me Me G.sub.194Me Me Me G.sub.196Me Me Me G.sub.197Me Me Me G.sub.198Me Me Me G.sub.209Me Me Me G.sub.213Me Me Me G.sub.214Me Me Me G.sub.215Me Me Me G.sub.219Me Me Me G.sub.220Me Me Me G.sub.221Me Me Me G.sub.222Me Me Me G.sub.224Me Me Me G.sub.226Me Me Me G.sub.229Me Me Me G.sub.232Me Me Me G.sub.235Me Me Me G.sub.236Me Me Me G.sub.238Me Me Me G.sub.248Me Me Me G.sub.250Me Me Me G.sub.259Me Me Me G.sub.262Me Me Me G.sub. 265Me Me Me G.sub.267Me Me Me G.sub.268Me Me Me G.sub.269Me Me Me G.sub.270Me Me Me G.sub.271Me Me Me G.sub.272Me Me Me G.sub.273Me Me Me G.sub.274Me Me Me G.sub.275Me Me Me G.sub.276Me Me Me G.sub.277Me Me Me G.sub.278Me Me Me G.sub.280Me Me Me G.sub.283Me Me Me G.sub.286Me Me Me G.sub.289Me Me Me G.sub.292Me Me Me G.sub.295Me Me Me G.sub.296Me Me Me G.sub.298Me Me Me G.sub.299Me Me Me G.sub.301Me Me Me G.sub.302Me Me Me G.sub.304Me Me Me G.sub.305Me Me Me G.sub.309Me Me Me G.sub.310Me Me Me G.sub.311Me Me Me G.sub.316Me Me Me G.sub.317Me Me Me G.sub.319Me Me Me G.sub.320Me Me Me G.sub.328Me Me Me G.sub.329Me Me Me G.sub.334Me Me Me G.sub.335Me Me Me G.sub.343Me Me Me G.sub.344Me Me Me G.sub.346Me Me Me G.sub. 347Me Me Me G.sub.349Me Me Me G.sub.350Me Me Me G.sub.352Me Me Me G.sub.353Me Me Me G.sub.355Me Me Me G.sub.356Me Me Me G.sub.358Me Me Me G.sub.359Me Me Me G.sub.364Me Me Me G.sub.367Me Me Me G.sub.370Me Me Me G.sub.373Me Me Me G.sub.376Me Me Me G.sub.377Me Me Me G.sub.382Me Me Me G.sub.383Me Me Me G.sub.385Me Me Me G.sub.386Me Me Me G.sub.394Me Me Me G.sub.395Me Me Me G.sub.403Me Me Me G.sub.406Me Me Me G.sub.409Me Me Me G.sub.415Me Me Me G.sub.421Me Me Me G.sub.427Me Me Me G.sub.430Me Me Me G.sub.439Me Me Me G.sub.448Me Me Me G.sub.451Me Me Me G.sub.454Me Me Me G.sub.455Me Me Me G.sub.457Me Me Me G.sub.458Me Me Me G.sub.463Me Me Me G.sub.464Me Me Me G.sub.469Me Me Me G.sub.472Me Me Me G.sub.475Me Me Me G.sub. 478Me Me Me G.sub.484Me Me Me G.sub.498Me Me Me G.sub.499Me Me Me G.sub.500Me Me Me G.sub.501Me Me Me G.sub.503Me Me Me G.sub.504Me Me Me G.sub.505Me Me Me G.sub.506Me Me Me G.sub.507Me Me Me G.sub.508Me Me Me G.sub.509Me Me Me G.sub.510Me Me Me G.sub.511Me Me Me G.sub.512Me Me Me G.sub.513Me Me Me G.sub.514Me Me Me G.sub.515Me Me Me G.sub.537Me Me Me G.sub.538Me Me Me G.sub.539Me Me Me G.sub.543Me Me Me G.sub.544Me Me Me G.sub.545Me Me Me G.sub.549Me Me Me G.sub.550Me Me Me G.sub.551Me Me Me G.sub.555Me Me Me G.sub.556Me Me Me G.sub.557Me Me Me G.sub.561Me Me Me G.sub.562Me Me Me G.sub.563Me Me Me G.sub.567Me Me Me G.sub.568Me Me Me G.sub.569Me Me Me G.sub.573Me Me Me G.sub.574Me Me Me G.sub.575Me Me Me G.sub. 579Me Me Me G.sub.580Me Me Me G.sub.581Me Me Me G.sub.585Me Me Me G.sub.586Me Me Me G.sub.587Me Me Me G.sub.593Me Me Me G.sub.598Me Me Me G.sub.599Me Me Me G.sub.601Me Me Me G.sub.606Me Me Me G.sub.608Me Me Me G.sub.610Me Me Me G.sub.611Me Me Me G.sub.612Me Me Me G.sub.613Me Me Me G.sub.614Me Me Me G.sub.615Me Me Me G.sub.617Me Me Me G.sub.618Me Me Me G.sub.620Me Me Me G.sub.621Me Me Me G.sub.622Me Me Me G.sub.626Me Me Me G.sub.627Me Me Me G.sub.628Me Me Me G.sub.632Me Me Me G.sub.633Me Me Me G.sub.634Me Me Me G.sub.638Me Me Me G.sub.639Me Me Me G.sub.640Me Me Me G.sub.643Me Me Et G.sub.3Me Me Et G.sub.6Me Me Et G.sub.268Me Me Et G.sub.269Me Me Et G.sub.271Me Me Et G.sub.272Me Me Et G.sub.274Me Me Et G.sub. 275Me Me Et G.sub.277Me Me Et G.sub.278Me Me Et G.sub.355Me Me Ph G.sub.3Me Me Ph G.sub.6Me Et Et G.sub.3Me Et Et G.sub.6Me (CH.sub.2).sub.4 G.sub.3Me (CH.sub.2).sub.4 G.sub.6Me (CH.sub.2).sub.5 G.sub.3Me (CH.sub.2).sub.5 G.sub.6Et Me Me G.sub.3Et Me Me G.sub.6Et Me Me G.sub.268Et Me Me G.sub.269Et Me Me G.sub.271Et Me Me G.sub.272Et Me Me G.sub.274Et Me Me G.sub.275Et Me Me G.sub.277Et Me Me G.sub.278Et Me Me G.sub.355Et Me Et G.sub.3Et Me Et G.sub.6Et Me Ph G.sub.3Et Me Ph G.sub.6Et Et Et G.sub.3Et Et Et G.sub.6Et (CH.sub.2).sub.4 G.sub.3Et (CH.sub.2).sub.4 G.sub.6Et (CH.sub.2).sub.5 G.sub.3Et (CH.sub.2).sub.5 G.sub.6Pr-n Me Me G.sub.3Pr-n Me Me G.sub.6Pr-i Me Me G.sub.3Pr-i Me Me G.sub.6cyc-Pr Me Me G.sub.3cyc-Pr Me Me G.sub.6cyc-Pr Me Me G.sub.268cyc-Pr Me Me G.sub.269cyc-Pr Me Me G.sub.271cyc-Pr Me Me G.sub.272cyc-Pr Me Me G.sub.274cyc-Pr Me Me G.sub.275cyc-Pr Me Me G.sub.277cyc-Pr Me Me G.sub.278cyc-Pr Me Me G.sub.355cyc-PrCH.sub.2 Me Me G.sub.3cyc-PrCH.sub.2 Me Me G.sub.6Bu-n Me Me G.sub.3Bu-n Me Me G.sub.6Bu-sec Me Me G.sub.3Bu-sec Me Me G.sub.6Bu-i Me Me G.sub.3Bu-i Me Me G.sub.6cyc-Bu Me Me G.sub.3cyc-Bu Me Me G.sub.6Bu-t Me Me G.sub.3Bu-t Me Me G.sub.6CH.sub.2CHCH.sub.2 Me Me G.sub.3CH.sub.2CHCH.sub.2 Me Me G.sub.6CHCCH.sub.2 Me Me G.sub.3CHCCH.sub.2 Me Me G.sub.6cyc-Pen Me Me G.sub.3cyc-Pen Me Me G.sub.6cyc-Hex Me Me G.sub.3cyc-Hex Me Me G.sub.6MeOCH.sub.2 CH.sub.2 Me Me G.sub.3MeOCH.sub.2 CH.sub.2 Me Me G.sub.6MeOCH.sub.2 (CH.sub.3)CH Me Me G.sub.3MeOCH.sub.2 (CH.sub.3)CH Me Me G.sub.6CHF.sub.2 OCH.sub.2 Me Me G.sub.3CHF.sub.2 OCH.sub.2 Me Me G.sub.6FCH.sub.2 Me Me G.sub.3FCH.sub.2 Me Me G.sub.6FCH.sub.2 CH.sub.2 Me Me G.sub.3FCH.sub.2 CH.sub.2 Me Me G.sub.6ClCH.sub.2 CH.sub.2 Me Me G.sub.3ClCH.sub.2 CH.sub.2 Me Me G.sub.6CF.sub.3 CH.sub.2 Me Me G.sub.3CF.sub.3 CH.sub.2 Me Me G.sub.6NCCH.sub.2 Me Me G.sub.3NCCH.sub.2 Me Me G.sub.6MeO.sub.2 CCH.sub.2 Me Me G.sub.3MeO.sub.2 CCH.sub.2 Me Me G.sub.6MeO.sub.2 CCH.sub.2 Me Me G.sub.268MeO.sub.2 CCH.sub.2 Me Me G.sub.269MeO.sub.2 CCH.sub.2 Me Me G.sub.271MeO.sub.2 CCH.sub.2 Me Me G.sub.272MeO.sub.2 CCH.sub.2 Me Me G.sub.274MeO.sub.2 CCH.sub.2 Me Me G.sub.275MeO.sub.2 CCH.sub.2 Me Me G.sub.277MeO.sub.2 CCH.sub.2 Me Me G.sub.278MeO.sub.2 CCH.sub.2 Me Me G.sub.355MeCOCH.sub.2 Me Me G.sub.3MeCOCH.sub.2 Me Me G.sub.6PhCH.sub.2 Me Me G.sub.3PhCH.sub.2 Me Me G.sub.6Ph Me Me G.sub.3Ph Me Me G.sub.6Ph Me Me G.sub.268Ph Me Me G.sub.269Ph Me Me G.sub.271Ph Me Me G.sub.272Ph Me Me G.sub.274Ph Me Me G.sub.275Ph Me Me G.sub.277Ph Me Me G.sub.278Ph Me Me G.sub.355Ph-2-Me Me Me G.sub.3Ph-2-Me Me Me G.sub.6Ph-3-Me Me Me G.sub.3Ph-3-Me Me Me G.sub.6Ph-4-OMe Me Me G.sub.3Ph-4-OMe Me Me G.sub.6Ph-3-OMe Me Me G.sub.3Ph-3-OMe Me Me G.sub.6Ph-2-OMe Me Me G.sub.3Ph-2-OMe Me Me G.sub.6Ph-4-Cl Me Me G.sub.3Ph-4-Cl Me Me G.sub.6Ph-3-Cl Me Me G.sub.3Ph-3-Cl Me Me G.sub.6Ph-2-Cl Me Me G.sub.3Ph-2-Cl Me Me G.sub.6Ph-2,6-Cl.sub.2 Me Me G.sub.3Ph-2,6-Cl.sub.2 Me Me G.sub.6______________________________________
TABLE 2A______________________________________ ##STR159##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me G.sub.3Me Me Me G.sub.6Me Me Me G.sub.268Me Me Me G.sub.269Me Me Me G.sub.271Me Me Me G.sub.272Me Me Me G.sub.274Me Me Me G.sub.275Me Me Me G.sub.277Me Me Me G.sub.278Me Me Me G.sub.355Me Me Et G.sub.3Me Me Et G.sub.6Me Me Ph G.sub.3Me Me Ph G.sub.6Et Me Me G.sub.3Et Me Me G.sub.6Et Me Me G.sub.268Et Me Me G.sub.269Et Me Me G.sub.271Et Me Me G.sub.272Et Me Me G.sub.274Et Me Me G.sub.275Et Me Me G.sub.277Et Me Me G.sub.278Et Me Me G.sub.355Pr-n Me Me G.sub.3Pr-n Me Me G.sub.6Pr-i Me Me G.sub.3Pr-i Me Me G.sub.6CH.sub.2CHCH.sub.2 Me Me G.sub.3CH.sub.2CHCH.sub.2 Me Me G.sub.6CHCCH.sub.2 Me Me G.sub.3CHCCH.sub.2 Me Me G.sub.6MeOCH.sub.2 Me Me G.sub.3MeOCH.sub.2 Me Me G.sub.6MeSCH.sub.2 Me Me G.sub.3MeSCH.sub.2 Me Me G.sub.6MeO.sub.2 CCH.sub.2 Me Me G.sub.3MeO.sub.2 CCH.sub.2 Me Me G.sub.6Ph Me Me G.sub.3Ph Me Me G.sub.6PhCH.sub.2 Me Me G.sub.3PhCH.sub.2 Me Me G.sub.6______________________________________
TABLE 3A______________________________________ ##STR160##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me G.sub.3Me Me Me G.sub.6Me Me Me G.sub.268Me Me Me G.sub.269Me Me Me G.sub.271Me Me Me G.sub.272Me Me Me G.sub.274Me Me Me G.sub.275Me Me Me G.sub.277Me Me Me G.sub.278Me Me Me G.sub.355Et Me Me G.sub.3Et Me Me G.sub.6Pr-n Me Me G.sub.3Pr-n Me Me G.sub.6cyc-Pr Me Me G.sub.3cyc-Pr Me Me G.sub.6Me Me Et G.sub.3Me Me Et G.sub.6Me Et Me G.sub.3Me Et Me G.sub.6Me (CH.sub.2).sub.3 G.sub.3Me (CH.sub.2).sub.3 G.sub.6Me (CH.sub.2).sub.4 G.sub.3Me (CH.sub.2).sub.4 G.sub.6______________________________________
TABLE 4A______________________________________ ##STR161##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me G.sub.3Me Me Me G.sub.6Me Me Et G.sub.3Me Me Et G.sub.6Et Me Me G.sub.3Et Me Me G.sub.6Pr-n Me Me G.sub.3Pr-n Me Me G.sub.6CH.sub.2CHCH.sub.2 Me Me G.sub.3CH.sub.2CHCH.sub.2 Me Me G.sub.6CHCCH.sub.2 Me Me G.sub.3CHCCH.sub.2 Me Me G.sub.6______________________________________
TABLE 5A______________________________________ ##STR162##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me G.sub.3Me Me Me G.sub.6Me Me Et G.sub.3Me Me Et G.sub.6Et Me Me G.sub.3Et Me Me G.sub.6Pr-n Me Me G.sub.3Pr-n Me Me G.sub.6CH.sub.2CHCH.sub.2 Me Me G.sub.3CH.sub.2CHCH.sub.2 Me Me G.sub.6______________________________________
TABLE 6A______________________________________ ##STR163##R.sup.11 R.sup.12 R.sup.13 Gn______________________________________Me Me Me G.sub.3Me Me Me G.sub.6Et Me Me G.sub.3Et Me Me G.sub.6cyc-Pr Me Me G.sub.3cyc-Pr Me Me G.sub.6CH.sub.2CHCH.sub.2 Me Me G.sub.3CH.sub.2CHCH.sub.2 Me Me G.sub.6CHCCH.sub.2 Me Me G.sub.3CHCCH.sub.2 Me Me G.sub.6Me Me Et G.sub.3Me Me Et G.sub.6Me Et Me G.sub.3Me Et Me G.sub.6______________________________________
TABLE 7A______________________________________ ##STR164##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________H H H H G.sub.3H H H H G.sub.6Me H H H G.sub.3Me H H H G.sub.6Me H H H G.sub.268Me H H H G.sub.269Me H H H G.sub.271Me H H H G.sub.272Me H H H G.sub.274Me H H H G.sub.275Me H H H G.sub.277Me H H H G.sub.278Me H H H G.sub.355Me H H Me G.sub.3Me H H Me G.sub.6Me H H Me G.sub.268Me H H Me G.sub.269Me H H Me G.sub.271Me H H Me G.sub.272Me H H Me G.sub.274Me H H Me G.sub.275Me H H Me G.sub.277Me H H Me G.sub.278Me H H Me G.sub.355Me H H Et G.sub.3Me H H Et G.sub.6Me H Me Me G.sub.3Me H Me Me G.sub.6Et H H H G.sub.3Et H H H G.sub.6Et H H H G.sub.268Et H H H G.sub.269Et H H H G.sub.271Et H H H G.sub.272Et H H H G.sub.274Et H H H G.sub.275Et H H H G.sub.277Et H H H G.sub.278Et H H H G.sub.355Pr-n H H H G.sub.3Pr-n H H H G.sub.6Pr-i H H H G.sub.3Pr-i H H H G.sub.6Bu-n H H H G.sub.3Bu-n H H H G.sub.6Bu-t H H H G.sub.3Bu-t H H H G.sub.6CH.sub.2CHCH.sub.2 H H H G.sub.3CH.sub.2CHCH.sub.2 H H H G.sub.6CHCCH.sub.2 H H H G.sub.3CH CCH.sub.2 H H H G.sub.6MeOCH.sub.2 H H H G.sub.3MeOCH.sub.2 H H H G.sub.6MeO.sub.2 CCH.sub.2 H H H G.sub.3MeO.sub.2 CCH.sub.2 H H H G.sub.6______________________________________
TABLE 8A______________________________________ ##STR165##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn______________________________________Me H H H H G.sub.1Me H H H H G.sub.3Me H H H H G.sub.5Me H H H H G.sub.6Me H H H H G.sub.7Me H H H H G.sub.8Me H H H H G.sub.11Me H H H H G.sub.12Me H H H H G.sub.13Me H H H H G.sub.14Me H H H H G.sub.15Me H H H H G.sub.16Me H H H H G.sub.19Me H H H H G.sub.20Me H H H H G.sub.23Me H H H H G.sub.25Me H H H H G.sub.26Me H H H H G.sub.27Me H H H H G.sub.29Me H H H H G.sub.31Me H H H H G.sub.34Me H H H H G.sub.36Me H H H H G.sub.39Me H H H H G.sub.41Me H H H H G.sub.42Me H H H H G.sub.44Me H H H H G.sub.99Me H H H H G.sub.100Me H H H H G.sub.103Me H H H H G.sub.116Me H H H H G.sub.117Me H H H H G.sub.120Me H H H H G.sub.121Me H H H H G.sub.122Me H H H H G.sub.123Me H H H H G.sub.124Me H H H H G.sub.125Me H H H H G.sub.126Me H H H H G.sub.129Me H H H H G.sub.132Me H H H H G.sub.144Me H H H H G.sub.180Me H H H H G.sub.181Me H H H H G.sub.189Me H H H H G.sub.190Me H H H H G.sub.192Me H H H H G.sub. 193Me H H H H G.sub.194Me H H H H G.sub.196Me H H H H G.sub.197Me H H H H G.sub.198Me H H H H G.sub.209Me H H H H G.sub.213Me H H H H G.sub.214Me H H H H G.sub.215Me H H H H G.sub.219Me H H H H G.sub.220Me H H H H G.sub.221Me H H H H G.sub.222Me H H H H G.sub.224Me H H H H G.sub.226Me H H H H G.sub.229Me H H H H G.sub.232Me H H H H G.sub.235Me H H H H G.sub.236Me H H H H G.sub.238Me H H H H G.sub.248Me H H H H G.sub.250Me H H H H G.sub.259Me H H H H G.sub.262Me H H H H G.sub.265Me H H H H G.sub.267Me H H H H C.sub.268Me H H H H C.sub.269Me H H H H G.sub.270Me H H H H G.sub.271Me H H H H G.sub.272Me H H H H G.sub.273Me H H H H G.sub.274Me H H H H G.sub.275Me H H H H G.sub.276Me H H H H G.sub.277Me H H H H G.sub.278Me H H H H G.sub.280Me H H H H G.sub.283Me H H H H G.sub.286Me H H H H G.sub.289Me H H H H G.sub.292Me H H H H G.sub.295Me H H H H G.sub.296Me H H H H G.sub.298Me H H H H G.sub.299Me H H H H G.sub.301Me H H H H G.sub.302Me H H H H G.sub.304Me H H H H G.sub.305Me H H H H G.sub.309Me H H H H G.sub.310Me H H H H G.sub.311Me H H H H G.sub.316Me H H H H G.sub.317Me H H H H G.sub.320Me H H H H G.sub.328Me H H H H G.sub.329Me H H H H G.sub.334Me H H H H G.sub.335Me H H H H G.sub.343Me H H H H G.sub.344Me H H H H G.sub.346Me H H H H G.sub.347Me H H H H G.sub.349Me H H H H G.sub.350Me H H H H G.sub.352Me H H H H G.sub.353Me H H H H G.sub.355Me H H H H G.sub.356Me H H H H G.sub.358Me H H H H G.sub.359Me H H H H G.sub.364Me H H H H G.sub.367Me H H H H G.sub.370Me H H H H G.sub.373Me H H H H G.sub.376Me H H H H G.sub.377Me H H H H G.sub.382Me H H H H G.sub.383Me H H H H G.sub.385Me H H H H G.sub.386Me H H H H G.sub.394Me H H H H G.sub.395Me H H H H G.sub.403Me H H H H G.sub.406Me H H H H G.sub.409Me H H H H G.sub.415Me H H H H G.sub.421Me H H H H G.sub.427Me H H H H G.sub.430Me H H H H G.sub.439Me H H H H G.sub.448Me H H H H G.sub.451Me H H H H G.sub.454Me H H H H G.sub.455Me H H H H G.sub.457Me H H H H G.sub.458Me H H H H G.sub.463Me H H H H G.sub.464Me H H H H G.sub.469Me H H H H G.sub.472Me H H H H G.sub.475Me H H H H G.sub.478Me H H H H G.sub.484Me H H H H G.sub.498Me H H H H G.sub.499Me H H H H G.sub.500Me H H H H G.sub.501Me H H H H G.sub.503Me H H H H G.sub.504Me H H H H G.sub.505Me H H H H G.sub.506Me H H H H G.sub.507Me H H H H G.sub.508Me H H H H G.sub.509Me H H H H G.sub.510Me H H H H G.sub.511Me H H H H G.sub.512Me H H H H G.sub.513Me H H H H G.sub.514Me H H H H G.sub.515Me H H H H G.sub.537Me H H H H G.sub.538Me H H H H G.sub.539Me H H H H G.sub.543Me H H H H G.sub.544Me H H H H G.sub.545Me H H H H G.sub.549Me H H H H G.sub.550Me H H H H G.sub.551Me H H H H G.sub.555Me H H H H G.sub.556Me H H H H G.sub.557Me H H H H G.sub.561Me H H H H G.sub.562Me H H H H G.sub.563Me H H H H G.sub.567Me H H H H G.sub.568Me H H H H G.sub.569Me H H H H G.sub.573Me H H H H G.sub.574Me H H H H G.sub.575Me H H H H G.sub.579Me H H H H G.sub.580Me H H H H G.sub.581Me H H H H G.sub.585Me H H H H G.sub.586Me H H H H G.sub.587Me H H H H G.sub.593Me H H H H G.sub.598Me H H H H G.sub.599Me H H H H G.sub.601Me H H H H G.sub.606Me H H H H G.sub.608Me H H H H G.sub.610Me H H H H G.sub.611Me H H H H G.sub.612Me H H H H G.sub.613Me H H H H G.sub.614Me H H H H G.sub.615Me H H H H G.sub.617Me H H H H G.sub.618Me H H H H G.sub.620Me H H H H G.sub.621Me H H H H G.sub.622Me H H H H G.sub.626Me H H H H G.sub.627Me H H H H G.sub.628Me H H H H G.sub.632Me H H H H G.sub.633Me H H H H G.sub.634Me H H H H G.sub.638Me H H H H G.sub.639Me H H H H G.sub.640Me H H H H G.sub.643Me H H H Me G.sub.3Me H H H Me G.sub.6Me H H H Me G.sub.268Me H H H Me G.sub.269Me H H H Me G.sub.271Me H H H Me G.sub.272Me H H H Me G.sub.274Me H H H Me G.sub.275Me H H H Me G.sub.277Me H H H Me G.sub.278Me H H H Me G.sub.355Me Me H H H G.sub.3Me Me H H H G.sub.6Et H H H H G.sub.3Et H H H H G.sub.6Et H H H H G.sub.268Et H H H H G.sub.269Et H H H H G.sub.271Et H H H H G.sub.272Et H H H H G.sub.274Et H H H H G.sub.275Et H H H H G.sub.277Et H H H H G.sub.278Et H H H H G.sub. 355Pr-n H H H H G.sub.3Pr-n H H H H G.sub.6CH.sub.2CHCH.sub.2 H H H H G.sub.3CH.sub.2CHCH.sub.2 H H H H G.sub.6CH CCH.sub.2 H H H H G.sub.3CH CCH.sub.2 H H H H G.sub.6______________________________________
TABLE 9A______________________________________ ##STR166##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________Me H H H G.sub.3Me H H H G.sub.6Me H H H G.sub.268Me H H H G.sub.269Me H H H G.sub.271Me H H H G.sub.272Me H H H G.sub.274Me H H H G.sub.275Me H H H G.sub.277Me H H H G.sub.278Me H H H G.sub.355Me H H Me G.sub.3Me H H Me G.sub.6Et H H H G.sub.3Et H H H G.sub.6CH.sub.2CHCH.sub.2 H H H G.sub.3CH.sub.2CHCH.sub.2 H H H G.sub.6CHCCH.sub.2 H H H G.sub.3CHCCH.sub.2 H H H G.sub.6______________________________________
TABLE 10A______________________________________ ##STR167##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn______________________________________Me H H H H G.sub.3Me H H H H G.sub.6Me H H H H G.sub.268Me H H H H G.sub.269Me H H H H G.sub.271Me H H H H G.sub.272Me H H H H G.sub.274Me H H H H G.sub.275Me H H H H G.sub.277Me H H H H G.sub.278Me H H H H G.sub.355Et H H H H G.sub.3Et H H H H G.sub.6CH.sub.2CHCH.sub.2 H H H H G.sub.3CH.sub.2CHCH.sub.2 H H H H G.sub.6CH CCH.sub.2 H H H H G.sub.3CHCCH.sub.2 H H H H G.sub.6______________________________________
TABLE 11A______________________________________ ##STR168##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________Me H H H G.sub.3Me H H H G.sub.6Me H H Me G.sub.3Me H H Me G.sub.6______________________________________
TABLE 12A______________________________________ ##STR169##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn______________________________________Me H H H H G.sub.3Me H H H H G.sub.6Et H H H H G.sub.3Et H H H H G.sub.6______________________________________
TABLE 13A______________________________________ ##STR170##R.sup.21 R.sup.22 R.sup.23 R.sup.24 Gn______________________________________Me H H H G.sub.3Me H H H G.sub.6Me H H Me G.sub.3Me H H Me G.sub.6______________________________________
TABLE 14A______________________________________ ##STR171##R.sup.21 R.sup.25 R.sup.26 R.sup.27 R.sup.28 Gn______________________________________Me H H H H G.sub.3Me H H H H G.sub.6Et H H H H G.sub.3Et H H H H G.sub.6______________________________________
The compound of the present invention can be applied to control various weeds not only in the agricultural and horticultural fields such as upland fields, paddy fields or orchards, but also in non-agricultural fields such as play grounds, non-used vacant fields or railway sides.
The dose varies depending upon the application site, the season for application, the manner of application, the type of weeds to be controlled, the type of crop plants, etc. However, the dose is usually within a range of from 0.0001 to 10 kg per hectare, preferably from 0.005 to 5 kg per hectare, as the amount of the active ingredient.
Further, the compound of the present invention may be combined with other herbicides, various insecticides, fungicides, plant growth regulating agents and synergism agents at the time of the preparation of the formulations or at the time of the application, as the case requires.
Particularly, by the combined application with other herbicide, it can be expected to reduce the cost due to a decrease of the dose or to enlarge the herbicidal spectrum or obtain higher herbicidal effects due to a synergistic effect of the combined herbicides. In such a case, the compound of the present invention may be combined with a plurality of known herbicides. The herbicides of the type which can be used in combination with the compound of the present invention, may, for example, be compounds disclosed in Farm Chemicals Handbook (1990).
When the compound of the present invention is to be used as a herbicide, it is usually mixed with a suitable carrier, for instance, a solid carrier such as clay, talc, bentonite, diatomaceous earth or fine silica powder, or a liquid carrier such as water, an alcohol (such as isopropanol, butanol, benzyl alcohol or furfuryl alcohol), an aromatic hydrocarbon (such as toluene or xylene), an ether (such as anisole), a ketone (such as cyclohexanone or isophorone), an ester (such as butyl acetate), an acid amide (such as N-methylpyrrolidone), or a halogenated hydrocarbon (such as chlorobenzene). If desired, a surfactant, an emulsifier, a dispersing agent, a penetrating agent, a spreader, a thickener, an antifreezing agent, a coagulation preventing agent or a stabilizer may be added to prepare an optional formulation such as a liquid formulation, an emulsifiable concentrate, a wettable powder, a dry flowable, a flowable, a dust or a granule.
Now, Formulation Examples of the herbicides containing the compounds of the present invention as active ingredients, will be given. However, it should be understood that the present invention is by no means restricted to such specific Examples. In the following Formulation Examples, "parts" means "parts by weight".
______________________________________Wettable powder______________________________________Compound of the present invention 5-80 partsSolid carrier 10-85 partsSurfactant 1-10 partsOther 1-5 parts______________________________________
As other, a coagulation preventing agent may, for example, be mentioned.
______________________________________Emulsifiable concentrateCompound of the present invention 1-30 partsLiquid carrier 30-95 partsSurfactant 5-15 partsFlowableCompound of the present invention 5-70 partsLiquid carrier 15-65 partsSurfactant 5-12 partsOther 5-30 parts______________________________________
As other, an antifreezing agent and a thickener may, for example, be mentioned.
______________________________________Granular wettable powder (dry flowable)Compound of the present invention 20-90 partsSolid carrier 10-60 partsSurfactant 1-20 parts GranuleCompound of the present invention 0.1-10 partsSolid carrier 90-99.99 partsOther 1-5 parts______________________________________
FORMULATION EXAMPLE 1
Wettable powder
______________________________________Compound No. 2 of the present invention 20 partsZeeklite A (tradename for a kaolin-type 76 partsclay, manufactured by Zeeklite Industries,Co., Ltd.)Sorpol 5039 (tradename for a mixture of a 2 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)Carplex (tradename for a coagulation- 2 partspreventing agent composed of a mixture of asurfactant and fine silica powder,manufactured by Shionogi PharmaceuticalCo., Ltd.)______________________________________
The above ingredients are homogeneously pulverized and mixed to form a wettable powder.
FORMULATION EXAMPLE 2
Wettable powder
______________________________________Compound No. 3 of the present invention 40 partsZeeklite A (tradename for a kaolin-type 54 partsclay, manufactured by Zeeklite Industries,Co., Ltd.)Sorpol 5039 (tradename for a mixture of a 2 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)Carplex (tradename for a coagulation- 4 partspreventing agent composed of a mixture of asurfactant and fine silica powder,manufactured by Shionogi PharmaceuticalCo., Ltd.)______________________________________
The above ingredients are homogeneously pulverized and mixed to form a wettable powder.
FORMULATION EXAMPLE 3
Emulsifiable concentrate
______________________________________Compound No. 5 of the present invention 5 partsXylene 75 partsN,N-dimethylformamide 15 partsSorpol 2680 (tradename for a mixture of a 5 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)______________________________________
The above ingredients are homogeneously mixed to form an emulsifiable concentrate.
FORMULATION EXAMPLE 4
Flowable
______________________________________Compound No. 6 of the present invention 25 partsAgrizole S-710 (tradename for a nonionic 10 partssurfactant, manufactured by Kao Corp.)Runox 1000C (tradename for an anionic 0.5 partsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)1% Rodopol water (tradename for a thickener, 20 partsmanufactured by Rhone-Poulenc)Water 44.5 parts______________________________________
The above ingredients were homogeneously mixed to obtain a flowable.
FORMULATION EXAMPLE 5
Flowable
______________________________________Compound No. 11 of the present invention 40 partsAgrizole S-710 (tradename for a nonionic 10 partssurfactant, manufactured by Kao Corp.)Runox 1000C (tradename for an anionic 0.5 partsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)1% Rodopol water (tradename for a thickener, 20 partsmanufactured by Rhone-Poulenc)Water 29.5 parts______________________________________
The above ingredients were homogeneously mixed to obtain a flowable.
FORMULATION EXAMPLE 6
Granular wettable powder (dry flowable)
______________________________________Compound No. 12 of the present invention 75 partsIsoban No. 1 (tradename for an anionic 10 partssurfactant, manufactured by Kuraray IsopreneChemical Co., Ltd.)Vanirex N (tradename for an anionic 5 partssurfactant, manufactured by Sanyo KokusakuPulp Co., Ltd.)Carplex #80 (tradename for fine silica powder, 10 partsmanufactured by Shionogi PharmaceuticalCo., Ltd.)______________________________________
The above ingredients are uniformly mixed and pulverized to form a dry flowable.
FORMULATION EXAMPLE 7
Granule
______________________________________Compound No. 13 of the present invention 1 partBentonite 55 partsTalc 44 parts______________________________________
The above ingredients were homogeneously mixed and pulverized, and after an addition of a small amount of water, the mixture was stirred, mixed and granulated by an extrusion-type granulating machine, followed by drying to obtain a granule.
FORMULATION EXAMPLE 8
Wettable powder
______________________________________Compound No. 14 of the present invention 20 partsZeeklite A (tradename for a kaolin-type 76 partsclay, manufactured by Zeeklite Industries,Co., Ltd.)Sorpol 5039 (tradename for a mixture of a 2 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)Carplex (tradename for a coagulation- 2 partspreventing agent composed of a mixture of asurfactant and fine silica powder,manufactured by Shionogi PharmaceuticalCo., Ltd.)______________________________________
The above ingredients are homogeneously pulverized and mixed to form a wettable powder.
FORMULATION EXAMPLE 9
Wettable powder
______________________________________Compound No. 15 of the present invention 40 partsZeeklite A (tradename for a kaolin-type 54 partsclay, manufactured by Zeeklite Industries,Co., Ltd.)Sorpol 5039 (tradename for a mixture of a 2 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)Carplex (tradename for a coagulation- 4 partspreventing agent composed of a mixture of asurfactant and fine silica powder,manufactured by Shionogi PharmaceuticalCo., Ltd.)______________________________________
The above ingredients are homogeneously pulverized and mixed to form a wettable powder.
FORMULATION EXAMPLE 10
Emulsifiable concentrate
______________________________________Compound No. 31 of the present invention 5 partsXylene 75 partsN,N-dimethylformamide 15 partsSorpol 2680 (tradename for a mixture of a 5 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)______________________________________
The above ingredients are homogeneously mixed to form an emulsifiable concentrate.
FORMULATION EXAMPLE 11
Flowable
______________________________________Compound No. 35 of the present invention 25 partsAgrizole S-710 (tradename for a nonionic 10 partssurfactant, manufactured by Kao Corp.)Runox 1000C (tradename for an anionic 0.5 partsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)1% Rodopol water (tradename for a thickener, 20 partsmanufactured by Rhone-Poulenc)Water 44.5 parts______________________________________
The above ingredients were homogeneously mixed to obtain a flowable.
FORMULATION EXAMPLE 12
Flowable
______________________________________Compound No. 42 of the present invention 40 partsAgrizole S-710 (tradename for a nonionic 10 partssurfactant, manufactured by Kao Corp.)Runox 1000C (tradename for an anionic 0.5 partsurfactant, manufactured by Toho ChemicalIndustry Co., Ltd.)1% Rodopol water (tradename for a thickener, 20 partsmanufactured by Rhone-Poulenc)Water 44.5 parts______________________________________
The above ingredients were homogeneously mixed to obtain a flowable.
FORMULATION EXAMPLE 13
Granular wettable powder (dry flowable)
______________________________________Compound No. 47 of the present invention 75 partsIsoban No. 1 (tradename for an anionic 10 partssurfactant, manufactured by Kuraray IsopreneChemical Co., Ltd.)Vanirex N (tradename for an anionic 5 partssurfactnt, manufactured by Sanyo KokusakuPulp Co., Ltd.)Carplex #80 (tradename for fine silica powder, 10 partsmanufactured by Shionogi PharmaceuticalCo., Ltd.)______________________________________
The above ingredients are uniformly mixed and pulverized to form a dry flowable.
FORMULATION EXAMPLE 14
Granule
______________________________________Compound No. 53 of the present invention 1 partBentonite 55 partsTalc 44 parts______________________________________
The above ingredients were homogeneously mixed and pulverized, and after an addition of a small amount of water, the mixture was stirred, mixed and granulated by an extrusion-type granulating machine, followed by drying to obtain a granule.
In use, the above wettable powder, emulsifiable concentrate, flowable or granular wettable powder is diluted with water from 50 to 1,000 times and applied so that the active ingredient will be from 0.0001 to 10 kg per hectare.
Now, the herbicidal activities of the compounds of the present invention will be described in detail with reference to the following Test Examples.
TEST EXAMPLE 1
Test on the herbicidal effects in soil treatment
A plastic box having a length of 15 cm, a width of 22 cm and a depth of 6 cm was filled with a sterilized diluvial soil, and seeds of Echinochloa crus-galli, Digitaria adscendens, Cyperus microiria, Solanum nigrum, Galinsoga ciliata, Rorippa indica, orvza sativa, Zea mays, Triticum aestivum, Glycine max and Gossypium herbaceum were sown, and the soil was covered thereon, and then a herbicide solution was applied by a small spray onto the surface of the soil uniformly so that the active ingredient was distributed at a predetermined concentration. The herbicide solution was prepared by diluting the formulation as described in the foregoing Formulation Examples with water and applied onto the entire soil surface. Three weeks after the application of the herbicidal solution, the herbicidal effects against each weed and the phytotoxicities against each crop plant were determined on the basis of the following standard ratings. The results are shown in Table 15.
Standard ratinqs:
5: Growth control rate of more than 90% (almost completely withered)
4: Growth control rate of from 70 to 90%
3: Growth control rate of from 40 to 70%
2: Growth control rate of from 20 to 40%
1: Growth control rate of from 5 to 20%
0: Growth control rate of less than 5% (almost non-effective)
The above growth control rates were calculated by the following equation: ##EQU1## where T: Weight of the weed grown above the soil surface of the treated area
N: Weight of the weed grown above the soil surface of the non-treated area
TEST EXAMPLE 2
Test on the herbicidal effects in foliage treatment
A plastic box having a length of 15 cm, a width of 22 cm and a depth of 6 cm was filled with a sterilized diluvial soil, and seeds of Echinochloa crus-galli, Digitaria adscendens, Cyperus microiria, Solanum nigrum, Galinsoga ciliata, Rorippa indica, oryza sativa, Zea mays, Triticum aestivum, Glycine max, Gossypium herbaceum and Beta vulgaris were spot-wisely sown. When the various weeds and crop plants grew to the 2 or 3 leaf stage, a herbicidal solution was uniformly sprayed on the foliages so that the active ingredient was applied in a predetermined concentration.
The herbicidal solution was prepared by diluting the formulation as described in the above Formulation Examples with water and applied onto the entire surface of the foliages of the weeds and the crop plants by a small spray. Three weeks after the application of the herbicide solution, the herbicidal effects against each weed and the phytotoxicities against each crop plant were determined on the basis of the standard ratings described in Test Example 1. The results are shown in Table 16.
In each Table, Compound Nos. correspond to Compound Nos. in the Examples, and symbols have the following meanings.
Dose: Dose of active ingredient (kg/ha)
N: Echinochloa crus-galli (barnyardgrass)
M: Digitaria adscendens (large crabgrass)
K: Cyperus microiria (annual sedge)
H: Solanum nigrum (black nightshade)
D: Galinsoga ciliata (hairy galinsoga)
I Rorippa indica (fieldcress)
R: Oryza sativa (rice)
T: Zea mays (corn)
S: Glycine max (soybean)
C: Gossypium herbaceum (cotton)
B: Beta vulgaris (sugar beet)
TABLE 15______________________________________Comp. Dose No. (kg/ha) N M K H D I R T W S C______________________________________ 1 0.16 1 2 2 4 5 5 0 0 0 3 2 0.32 2 3 3 5 5 5 0 0 0 4 3 0.63 3 4 4 5 5 5 2 1 1 5 4 2 0.16 2 3 3 5 5 5 3 0 0 2 3 0.32 4 4 4 5 5 5 4 1 1 3 4 0.63 5 5 5 5 5 5 5 2 4 4 5 3 0.16 2 2 2 5 5 5 0 0 0 2 2 0.32 3 4 4 5 5 5 1 0 1 3 3 0.63 4 5 5 5 5 5 3 1 3 4 4 4 0.16 1 1 1 4 5 5 1 0 0 1 1 0.32 2 2 2 5 5 5 2 0 0 2 2 0.63 3 3 3 5 5 5 4 1 1 3 4 5 0.16 3 3 3 5 5 5 0 0 0 2 2 0.32 4 3 4 5 5 5 1 1 1 3 3 0.63 5 4 5 5 5 5 2 3 3 4 4 6 0.16 2 2 1 5 5 5 3 0 0 2 3 0.32 4 4 2 5 5 5 4 0 1 3 4 0.63 5 5 3 5 5 5 5 2 4 4 5 7 0.63 3 4 4 5 5 5 3 0 0 2 2 8 0.16 1 2 2 4 5 5 3 0 0 2 2 0.32 2 2 2 5 5 5 4 0 0 3 3 0.63 3 3 3 5 5 5 5 1 2 3 4 9 0.16 0 0 0 3 5 5 0 0 0 0 0 0.32 1 1 1 4 5 5 0 0 0 1 1 0.63 2 2 3 5 5 5 0 0 0 2 2 10 0.16 0 1 0 3 5 5 0 0 0 1 0 0.32 1 2 1 4 5 5 1 0 0 2 1 0.63 2 3 2 5 5 5 2 0 0 3 3 11 0.16 4 4 4 5 5 5 0 0 0 3 3 0.32 5 5 4 5 5 5 1 0 0 4 3 0.63 5 5 5 5 5 5 4 0 1 4 4 14 0.04 1 2 1 5 5 5 2 0 0 0 0 0.08 2 4 2 5 5 5 3 0 0 1 1 0.16 3 5 4 5 5 5 3 1 2 4 2 15 0.04 1 2 1 4 5 5 0 0 0 1 0 0.08 2 3 2 5 5 5 0 0 0 2 1 0.16 3 4 3 5 5 5 0 0 0 2 3 16 0.63 1 3 3 4 5 5 1 0 0 1 0 17 0.63 3 4 3 5 5 5 0 0 0 4 2 19 0.16 0 1 1 5 4 5 0 0 0 0 0 0.32 1 1 2 5 5 5 0 0 0 1 1 0.63 2 3 3 5 5 5 0 0 0 2 2 20 0.16 2 1 1 5 4 5 0 0 0 2 1 0.32 3 1 2 5 5 5 0 0 0 3 2 0.63 4 2 3 5 5 5 2 0 0 4 4 21 0.16 3 3 4 5 5 5 2 0 1 2 2 0.32 4 4 5 5 5 5 3 0 2 3 3 0.63 5 5 5 5 5 5 4 1 3 4 4 22 0.16 2 3 4 5 5 5 4 0 4 0 2 0.32 4 4 5 5 5 5 5 1 5 1 3 0.63 5 5 5 5 5 5 5 2 5 3 4 23 0.63 1 2 3 5 5 5 0 0 0 0 2 27 0.63 2 3 2 5 5 5 3 0 3 4 3 28 0.63 2 3 3 5 5 5 2 0 4 4 4 32 0.63 1 2 1 5 5 5 0 0 1 2 1 33 0.16 1 1 0 5 5 4 0 0 0 3 0 0.32 3 4 1 5 5 5 2 0 1 4 1 0.63 5 5 3 5 5 5 4 1 3 5 2 34 0.63 1 2 2 4 5 5 3 0 1 4 4 35 0.63 1 2 1 4 5 5 0 1 0 3 3 42 0.63 3 4 3 5 5 5 5 3 3 4 3 43 0.16 2 3 3 4 5 5 3 0 0 1 2 0.32 3 4 3 5 5 5 4 1 0 2 3 0.63 4 4 4 5 5 5 4 2 0 4 4 47 0.63 4 5 3 4 5 4 4 1 1 0 0 48 0.16 0 1 2 4 4 5 0 0 0 1 1 0.32 1 2 3 5 5 5 0 0 0 2 2 0.63 2 4 4 5 5 5 1 0 0 3 2 49 0.16 2 4 1 4 5 5 3 0 2 2 3 0.32 3 5 2 5 5 5 4 0 3 3 3 0.63 4 5 3 5 5 5 5 1 4 4 4 52 0.16 2 3 2 5 5 5 4 0 2 4 4 0.32 3 4 3 5 5 5 5 1 3 5 5 0.63 3 4 3 5 5 5 5 2 3 5 5 53 0.16 2 4 2 5 5 5 5 0 4 5 4 0.32 4 5 3 5 5 5 5 1 5 5 5 0.63 5 5 4 5 5 5 5 3 5 5 5 55 0.16 1 1 2 4 5 5 2 0 0 0 0 0.32 2 3 3 5 5 5 3 0 1 1 1 0.63 4 5 4 5 5 5 4 0 3 4 3______________________________________
TABLE 16______________________________________ Dose Comp. (kg/ No. ha) N M K H D I R T W S C B______________________________________ 1 0.16 1 0 0 5 5 5 0 0 0 5 5 5 0.32 2 1 1 5 5 5 0 0 0 5 5 5 0.63 3 2 3 5 5 5 1 1 1 5 5 5 2 0.16 3 1 1 5 5 5 2 0 0 4 5 5 0.32 4 2 2 5 5 5 3 0 0 5 5 5 0.63 5 3 3 5 5 5 4 1 1 5 5 5 3 0.16 3 1 1 5 5 5 0 0 0 4 3 5 0.32 4 2 2 5 5 5 0 0 0 5 4 5 0.63 5 3 3 5 5 5 1 1 1 5 5 5 4 0.16 2 1 1 5 5 5 0 0 0 4 4 5 0.32 2 2 2 5 5 5 1 0 0 5 5 5 0.63 3 3 3 5 5 5 3 1 1 5 5 5 5 0.16 3 1 1 5 5 5 2 0 0 3 4 5 0.32 4 2 2 5 5 5 3 1 0 4 5 5 0.63 5 4 3 5 5 5 4 2 2 5 5 5 6 0.16 3 2 1 5 5 5 2 0 0 3 4 5 0.32 4 3 2 5 5 5 3 1 0 4 5 5 0.63 5 4 3 5 5 5 4 2 1 4 5 5 7 0.63 2 1 2 5 5 5 1 0 0 4 3 5 8 0.16 2 1 1 5 5 5 2 0 0 2 3 4 0.32 3 2 2 5 5 5 2 0 0 3 4 5 0.63 5 3 3 5 5 5 3 1 0 4 4 5 9 0.16 0 0 0 5 5 5 0 0 0 4 2 4 0.32 1 1 1 5 5 5 0 0 0 5 3 5 0.63 3 2 2 5 5 5 0 1 0 5 4 5 10 0.16 1 0 0 5 5 5 0 0 0 5 2 4 0.32 2 1 1 5 5 5 0 0 0 5 3 5 0.63 4 2 2 5 5 5 0 0 0 5 4 5 11 0.16 3 2 2 5 5 5 1 0 0 4 4 5 0.32 4 3 3 5 5 5 2 0 0 5 5 5 0.63 5 4 3 5 5 5 3 1 1 5 5 5 14 0.04 0 0 0 5 5 5 0 0 0 2 2 5 0.08 1 1 1 5 5 5 1 0 0 3 4 5 0.16 2 1 2 5 5 5 2 0 0 5 5 5 15 0.04 1 1 0 5 5 5 0 0 0 4 3 5 0.08 2 2 1 5 5 5 0 0 0 5 4 5 0.16 3 3 2 5 5 5 0 0 0 5 5 5 16 0.16 0 0 0 5 5 5 0 0 0 2 1 4 0.32 1 1 1 5 5 5 0 0 0 3 2 5 0.63 2 2 2 5 5 5 0 0 0 4 3 5 17 0.16 1 0 1 5 5 5 0 0 0 5 3 3 0.32 1 1 1 5 5 5 0 0 0 5 4 4 0.63 2 2 2 5 5 5 0 0 0 5 5 5 18 0.63 2 1 2 5 5 5 0 0 0 4 2 2 19 0.16 1 0 1 5 5 5 0 0 0 2 2 4 0.32 1 1 1 5 5 5 0 0 0 3 3 5 0.63 2 2 2 5 5 5 1 1 0 4 4 5 20 0.16 0 0 1 5 5 4 0 0 0 4 3 4 0.32 1 1 1 5 5 5 0 0 0 4 4 5 0.63 2 2 2 5 5 5 1 1 0 5 5 5 21 0.16 1 1 1 5 5 5 2 0 0 5 4 5 0.32 2 2 1 5 5 5 2 0 0 5 5 5 0.63 3 3 2 5 5 5 3 1 0 5 5 5 22 0.16 1 1 1 5 5 5 1 0 0 1 5 5 0.32 2 2 2 5 5 5 2 0 0 2 5 5 0.63 3 4 3 5 5 5 3 1 1 3 5 5 23 0.16 0 0 1 5 5 5 0 0 0 1 2 2 0.32 1 1 2 5 5 5 0 0 0 2 3 3 0.63 2 2 3 5 5 5 0 0 0 3 4 3 24 0.16 0 0 0 5 5 5 0 0 0 2 3 4 0.32 1 1 1 5 5 5 0 0 0 2 4 4 0.63 1 2 2 5 5 5 0 0 0 3 5 5 26 0.63 3 2 2 4 5 5 3 0 0 5 3 4 27 0.16 2 2 0 5 5 5 2 0 0 5 2 5 0.32 3 2 1 5 5 5 3 0 1 5 3 5 0.63 3 3 2 5 5 5 4 1 2 5 3 5 28 0.16 1 1 1 5 5 5 0 0 0 5 2 5 0.32 2 2 2 5 5 5 1 0 1 5 3 5 0.63 3 3 3 5 5 5 2 1 3 5 4 5 29 0.63 2 1 1 4 5 5 2 2 1 5 2 5 31 0.16 0 0 0 4 5 5 0 0 0 4 3 3 0.32 1 1 1 5 5 5 0 0 0 5 4 5 0.63 2 2 2 5 5 5 1 0 0 5 5 5 32 0.16 0 0 0 5 5 5 0 0 0 4 2 4 0.32 1 1 1 5 5 5 0 0 0 5 2 5 0.63 3 2 2 5 5 5 1 1 1 5 3 5 33 0.04 0 0 0 5 5 5 0 0 0 5 1 3 0.08 1 1 1 5 5 5 0 0 0 5 2 4 0.16 2 2 3 5 5 5 1 1 0 5 2 4 34 0.04 0 0 0 4 5 5 0 0 0 4 2 2 0.08 0 0 0 5 5 5 0 0 0 5 3 3 0.16 1 1 1 5 5 5 0 0 1 5 4 5 35 0.16 1 1 0 5 5 5 0 0 0 5 2 4 0.32 2 2 1 5 5 5 0 1 0 5 3 5 0.63 3 3 2 5 5 5 2 2 1 5 4 5 36 0.16 0 0 0 3 4 5 0 0 0 4 0 1 0.32 1 1 0 5 5 5 0 0 0 4 0 2 0.63 2 2 1 5 5 5 0 0 0 5 1 3 37 0.04 0 0 0 4 5 5 0 0 0 4 1 3 0.08 0 0 0 5 5 5 0 0 0 5 2 3 0.16 1 1 1 5 5 5 0 0 0 5 2 4 38 0.63 3 2 1 5 5 5 1 1 2 4 3 4 42 0.16 0 0 0 5 5 5 1 0 0 4 3 4 0.32 1 1 1 5 5 5 2 1 0 5 4 5 0.63 2 3 2 5 5 5 3 3 0 5 5 5 43 0.04 0 0 0 5 5 5 0 0 0 4 3 4 0.08 0 0 0 5 5 5 1 0 0 5 4 5 0.16 1 1 1 5 5 5 2 0 0 5 4 5 47 0.04 0 0 0 5 5 5 0 0 0 4 3 1 0.08 1 1 1 5 5 5 0 0 0 5 4 2 0.16 2 2 2 5 5 5 1 0 0 5 4 4 48 0.16 0 0 1 5 5 5 0 0 0 3 4 5 0.32 1 1 2 5 5 5 0 0 0 4 5 5 0.63 2 3 3 5 5 5 1 0 0 5 5 5 49 0.16 2 1 0 5 5 5 0 0 0 5 5 5 0.32 3 2 1 5 5 5 0 0 0 5 5 5 0.63 4 3 2 5 5 5 1 1 1 5 5 5 50 0.63 2 2 1 5 5 5 1 0 0 2 3 4 52 0.16 3 1 1 5 5 5 3 1 0 5 5 5 0.32 4 2 2 5 5 5 4 2 1 5 5 5 0.63 5 3 3 5 5 5 4 3 2 5 5 5 53 0.16 4 3 2 5 5 5 2 1 0 5 5 5 0.32 5 4 3 5 5 5 3 2 1 5 5 5 0.63 5 5 4 5 5 5 4 4 3 5 5 5 55 0.16 2 1 1 4 5 5 0 0 0 3 2 3 0.32 3 2 2 5 5 5 1 0 0 4 3 4 0.63 4 3 4 5 5 5 2 0 1 5 4 4______________________________________

Number	Date	Country
2-54455	Mar 1990	JPX
2-54456	Mar 1990	JPX
2-153345	Jun 1990	JPX
2-300127	Nov 1990	JPX
2-403735	Dec 1990	JPX

Sulfamidosulfonamide derivatives and herbicides

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Priority Claims (5)

US Referenced Citations (1)

Foreign Referenced Citations (1)