Substituted benzoyl derivatives and herbicidal compositions

BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to novel substituted benzoyl derivatives, processes for their production and herbicidal compositions containing them.
Discussion of Background
As a result of extensive researches over years, the present inventors have found that the compounds of the present invention have herbicidal activities remarkably high as compared with conventional herbicides, and many of the compounds of the present invention have excellent selectivity for certain crop plants, particularly for gramineous crop plants such as corn and wheat, and thus are practically useful. The present invention has been accomplished on the basis of these discoveries.
Namely, the compounds of the present invention are so effective that the dose of the active ingredient per unit area can substantially be reduced as compared with conventional herbicidal compounds, and their phytotoxicity against crop plants is extremely low as compared with conventional herbicides. Therefore, their economical effects are substantial. Further, with the compounds of the present invention, it is possible to substantially reduce a danger of environmental pollution due to application of agricultural chemicals in large amounts, and little adverse effects to other crop plants due to the effects remaining in soil are observed. Therefore, the compounds of the present invention may be regarded as epoch-making herbicides.
SUMMARY OF THE INVENTION
The present invention provides a substituted benzoyl derivative of the formula: ##STR2## wherein R is a lower alkyl group, or a phenyl group unsubstituted or substituted by a lower alkyl group, halogen atom or a lower alkoxy group;
n is an integer of 2 or 3;
m is an integer of from 0 to 6, and when m is an integer of from 2 to 6, the plurality of R may be the same or different from one another;
l is an integer of 0, 1 or 2;
X is a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower alkoxy group, or a lower haloalkyl group;
Y is a hydrogen atom, a halogen atom, a nitro group, a lower alkyl group unsubstituted or substituted by a halogen atom or a lower alkoxy group, a lower alkoxy group, or a lower alkoxy carbonyl group; and
Z is a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkylthio group, a lower alkylsulfinyl group, a lower haloalkylsulfinyl group, a lower alkylsulfonyl group, or a lower haloalkylsulfonyl group.
The present invention also provides a herbicidal composition comprising a herbicidally effective amount of the substituted benzoyl derivative of the formula I and an agricultural carrier or diluent.
Now, the present invention will be described in detail with reference to the preferred embodiments.
The compound of the present invention is a novel compound not disclosed in literatures and has excellent physiological activities as a herbicide.
The compound of the present invention takes the following three structures by tautomerism; ##STR3##
In the above formulas, R, n, m, l, X, Y and Z are as defined above. The compound of the formula I of the present invention can easily be produced by the following reaction. ##STR4## In the above formulas, Q.sup.1 is --N(CH.sub.3).sub.2, --N(CH.sub.2 CH.sub.3).sub.2, ##STR5## Q.sup.2 is a halogen atom, and R, n, m, l, X, Y and Z are as defined above.
The compound of the formula II (l=0) can be obtained in good yield in accordance with the reaction disclosed in e.g. Synthesis, p. 368 (1978), J. Amer. Chem. Soc. Vol. 74, p. 1569 (1952). The compound of the formula III can be prepared in accordance with the methods disclosed in e.g. Journal of the Chemical Society, p. 1406 (1934), and the Journal of Organic Chemistry, Vol. 39, p 725 (1974).
The compounds of the formulas II and III are reacted in a suitable solvent, if necessary in the presence of an organic base such as pyridine or triethylamine, whereby the compound of the formula I (l=0) of the present invention can be prepared in good yield. If necessary, the compound of the formula I (l=0) of the present invention is reacted with an oxidizing agent such as m-chloroperbenzoic acid or an aqueous hydrogen peroxide solution to obtain the compound of the formula I (l=1 or 2) of the present invention. Now, the compound of the formula I of the present invention will be described in further detail with reference to Preparation Examples of some representative compounds.

PREPARATION EXAMPLE 1 ##STR6##
To a solution of 27.6 g of tetrahydrothiopyran-3-one (J. Amer. Chem. Soc. 74, 1569 (1952)) in 300 ml of benzene, 20.3 g of pyrrolidine and 0.5 g of p-toluene sulfonic acid were added, and the mixture was refluxed for five hours by means of a Dean-Stark trap. After cooling the mixture, the solvent was distilled off, and the residue was subjected to distillation under reduced pressure to obtain 36.3 g of a fraction distilled at a temperature of from 98.degree. to 100.degree. C. under 0.3 mmHg (yield 89%). By the .sup.1 H-NMR analysis, the product was ascertained to be the above identified pyrrolidine enamine.
PREPARATION EXAMPLE 2 ##STR7##
To a solution of 9 g of 4-methyl-3-oxotetrahydrothiophene (Synthesis 368 (1978)) in 80 ml of benzene, 6 g of pyrrolidine and 0.1 g of p-toluenesulfonic acid were added, and the mixture was refluxed for 3 hours by means of a Dean-Stark trap. After cooling the mixture, the solvent was distilled off and the residue was subjected to distillation under reduced pressure to obtain 9.6 g of a fraction distilled at a temperature of from 70.degree. to 85.degree. C. under 0.2 mmHg (yield: 74%). From the .sup.1 H-NMR analysis, the product was ascertained to be the above identified enamine.
PREPARATION EXAMPLE 3
Compound No. 1 of the Present Invention ##STR8##
3.8 g (22 mmol) of the enamine obtained in Preparation Example 1 was dissolved in 60 ml of methylene chloride, and 2.45 g (24 mmol) of triethylamine was added thereto. Then, 4.7 g (22 mmol) of 2,4-dichlorobenzoic acid chloride was added thereto, and the mixture was stirred at room temperature overnight. Then, 18 ml of a 2.5N hydrochloric acid aqueous solution was added thereto, and the mixture was stirred for two hours. The reaction solution was extracted with methylene chloride, washed with water and then dried under anhydrous sodium sulfate. After filtration and removal of the solvent by distillation, the product was purified by column chromatography to obtain 3.26 g of a crystal product (melting point: 134.degree.-135.degree. C.). By the .sup.1 H-NMR and Mass analyses, the product was found to comprise two benzoyl molecules bonded to each other.
1.47 g (3.2 mmol) of the crystal product was dissolved in 10 ml of ethanol, and 10 ml of an aqueous solution having 0.27 g of sodium hydroxide dissolved therein, was added thereto. The mixture was stirred at room temperature overnight. Then, the mixture was acidified with an aqueous hydrochloric acid solution and then extracted with chloroform and dried. After filtration and removal of the solvent by distillation, the product was purified by column chromatography to obtain 0.68 g of a brown liquid. From the .sup.1 H-NMR and Mass analyses, the product was ascertained to be 2-(2,4-dichlorobenzoyl)-tetrahydrothiopyran-3-one [yield: 74%, brown liquid, refractive index n.sub.D 20 1.6288.
.sup.1 H-NMR .delta.value: ((CDCl.sub.3)) 2.16((tt, J=6Hz, 6Hz, 2H) 2.60(t, J=6Hz, 2H), 2.73(t, J=6Hz, 2H), 7.13(s, 2H), 7.31(s, 1H)]
PREPARATION EXAMPLE 4
Compound No. 1736 of the Present Invention ##STR9##
2.5 g (15 mmol) of the enamine obtained in Preparation Example 2 was dissolved in 50 ml of methylene chloride, and 1.65 g (16 mmol) of triethylamine was added thereto. Then, 3.1 g (14 mmol) of 2,4-dichlorobenzoic acid chloride was added thereto, and the mixture was stirred at room temperature overnight. To the reaction solution, 20 ml of a 2.5N hydrochloric acid aqueous solution was added, and the mixture was stirred at room temperature for 4 hours. Then, the mixture was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. After filtration and removal of the solvent by distillation, the product was purified by column chromatography to obtain 1.57 g of a crystal product. From the .sup.1 H-NMR and Mass analyses, the product was ascertained to be 2-(2,4-dichlorobenzoyl)-tetrahydrohydrothiophen-3-one.
[Yield: 37%, dark green crystal, melting point: 55.degree.-58.degree. C.,
.sup.1 H-NMR .delta.value: ((CDCl.sub.3)) 1.26-1.37(m, 3H), 2.73-3.28(m,3H), 7.25-7.50(m, 3H), 12.5-13.5(b,1H)]
PREPARATION EXAMPLE 5
Compound No. 32 of the Present Invention ##STR10##
2.5 g (15 mmol) of the enamine obtained in Preparation Example 1 was dissolved in 60 ml of methylene chloride, and then 4.4 g (44 mmol) of triethylamine and 0.05 g of 4-dimethylaminopyridine were added thereto. The mixture was cooled with ice. The, 3.2 g (14 mmol) of 4-chloro-2-nitrobenzoic acid chloride was gradually added thereto. The mixture was stirred at room temperature overnight. To the reaction solution, 20 ml of a 2.5 N hydrochloric acid aqueous solution was added, and the mixture was stirred for further three hours. The mixture was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. After filtration and removal of the solvent by distillation, the product was purified by column chromatography to obtain 1.38 g of a reddish brown crystal product. From the .sup.1 H-NMR and Mass analyses, the product was ascertained to be 2-(4-chloro-2-nitrobenzoyl)-tetrahydrothiopyran-3-one.
[Yield: 32%, reddish brown crystal,
melting point: 113.degree.-116.degree. C.,
.sup.1 H-NMR .delta.value: ((CDCl.sub.3)) 2.16((tt, J=6Hz, 6Hz, 2H), 2.61(t, J=6Hz, 2H), 2.72(t, J=6Hz, 2H), 7.34(d, J=8Hz, 1H), 7.71(dd, J=2Hz, J=8Hz, 1H), 8.15(d, J=2Hz, 1H)]
PREPARATION EXAMPLE 6
Compound No. 3 of the Present Invention ##STR11##
Two g (11.8 mmol) of the enamine obtained in Preparation Example 1 and 3.6 g (3equivalent) of triethylamine were dissolved in dry methylene chloride, and while cooling the mixture in an ice bath, 2.6 (11.8 mmol) of 2-chloro-4-nitrobenzoic acid chloride was dropwise added thereto, and the mixture was stirred at room temperature overnight.
Then, 20 ml of a 2N hydrochloric acid aqueous solution was added thereto, and the mixture was stirred for 3 hours. Then, water was added thereto, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and chloroform was distilled off under reduced pressure. The product was isolated by column chromatography to obtain 0.35 g (yield: 10%, melting point: 59.2.degree.-62.5.degree. C.) of desired 2-(2-chloro-4-nitrobenzoyl) tetrahydrothiopyran-3-one.
.sup.1 H-NMR .delta.value: ((CDCl.sub.3)) 2-3.2 ppm(m, 6H), 7.1-8.5 ppm(m, 3H), 15.2 ppm(br, 1H).
MS: M.sup.+ =299
Melting point: 59.5.degree.-62.5.degree. C.]
PREPARATION EXAMPLE 7
Compound No. 2 of the Present Invention ##STR12##
1.33 g (7.9 mmol) of the enamine prepared in Preparation Example 1 and 1.2 g (11.9 mmol) of triethylamine were dissolved in 60 ml of tetrahydrofuran and cooled with ice. Then, 2 g (7.9 mmol) of 2-chloro-4-methylsulfonylbenzoic acid chloride was dissolved in 10 ml of tetrahydrofuran and gradually added to the above solution. The mixture was stirred at room temperature for one hour and then stirred at a temperature of from 60.degree. to 70.degree. C. for two hours. After cooling the mixture, the solvent was distilled off, and 50 ml of chloroform and 20 ml of an aqueous hydrochloric acid solution were added to the residue, and the mixture was stirred at room temperature for one hour. Then, the product was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. After filtration and removal of the solvent by distillation, the product was purified by column chromatography to obtain 0.32 g of slightly yellow crystal. From the .sup.1 H-NMR analysis, the product was ascertained to be 2-(2-chloro-4-methylsulfonylbenzoyl)-tetrahydrothiopyran-3-one.
[Yield: 12%, slightly yellow crystal, melting point: 111.degree.-113.degree. C.,
.sup.1 H-NMR .delta.value: ((CDCl.sub.3)) 2.22(tt, J=6HZ, 2H), 2.68(t, J=6Hz, 2H), 2.79(t, J=6Hz, 2H), 3.09(s, 3H), 7.51(d, J=8Hz, 1H), 7.90(dd, J=2Hz, 8Hz, 1H), 8.00(d, J=2Hz, 1H), 15.77(b,1H)]
PREPARATION EXAMPLE 8
Compound No. 17 of the Present Invention ##STR13##
Two g (11.8 mmol) of the enamine obtained in Preparation Example 1 and 1.8 g (1.5 equivalent) of triethylamine were dissolved in 50 ml of dry tetrahydrofuran, and 2.4 g (9 mmol) of 2-chloro-3-methyl-4-methylsulfonylbenzoic acid chloride was dropwise added thereto while cooling with an ice bath, and the mixture was stirred at room temperature overnight.
Then, tetrahydrofuran was distilled off under reduced pressure, and then, 30 ml of chloroform was added thereto. Further, 20 ml of a 2N hydrochloric acid aqueous solution was added thereto, and the mixture was stirred for three hours. After an addition of water, the product was extracted with chloroform and dried over anhydrous sodium sulfate. Then, chloroform was distilled off under reduced pressure, and the product was purified by column chromatography to obtain 0.33 g (yield: 10.6%, melting point: 141.5.degree.-144.0.degree. C.) of 2-(2-chloro-3-methyl-4-methylsulfonylbenzoyl)-tetrahydrothiopyran-3-one.
1H-NMR .delta.value; ((CDCl.sub.3)) 1.8-3.0 ppm(m, 6H), 2.8 ppm(s, 3H), 3.1 ppm(s, 3H), 7.3 ppm(d, 2H), 8.05 ppm(d, 2H), 1.52 ppm(br, 1H)
MS: M.sup.+ =346, melting point: 14.5.degree.-144.0.degree. C.]
PREPARATION EXAMPLE 9
Compound No. 29 of the Present Invention ##STR14##
0.59 g (3.5 mmol) of the enamine obtained in Preparation Example 1 and 0.53 g (1.5 equivalent) of triethylamine were dissolved in 50 ml of dry tetrehydrofuran, and 0.93 g (3.5 mmol) of 2-methyl-3-ethoxycarbonyl- 4-methylsulfonylbenzoic acid chloride was dropwise added, while cooling the solution with an ice bath. The mixture was stirred at room temperature for two hours. The mixture was then heated to 65.degree. C. and stirred for further two hours.
Tetrahydrofuran was distilled off under reduced pressure, and 30 ml of chloroform was added to the residue. Further, 20 ml of a 2N hydrochloric acid aqueous solution was added thereto, and the mixture was stirred for 3 hours. After an addition of water, the product was extracted with chloroform and dried over anhydrous sodium sulfate. Chloroform was distilled off under reduced pressure, and the product was purified by column chromatography to obtain 0.13 g (yield: 10%) of 2-(2-methyl-3-ethoxycarbonyl-4-methylsulfonylbenzoyl)-tetrahydrothiopyran-3-one.
.sup.H -NMR .delta.value: ((CDCl.sub.3)) 1.4 ppm(t, 3H), 2.3 ppm(s, 3H), 3.2 ppm(s, 3H), 1.7-3.3 ppm(m, 6H), 4.5 ppm(q, 2H), 7.1-8.2 ppm (m, 2H), 15.5 ppm(br)]
PREPARATION EXAMPLE 10
Compound No. 30 of the Present Invention ##STR15##
0.8 g (4.7 mmol) of the enamine obtained in Preparation Example 1 and 0.93 g (2 equivalent) of triethylamine were dissolved in 50 ml of dry tetrahydrofuran. Then, 1.27 g (4.6 mmol) of 2-methyl-3-methoxymethyl-4-methylsulfonylbenzoic acid chloride was dropwise added thereto while cooling with an ice bath. The mixture was stirred at room temperature overnight. Then, tetrahydrofuran was distilled off under reduced pressure, and 30 ml of chloroform was added to the residue, and 20 ml of a 2N hydrochloric acid aqueous solution was further added thereto. The mixture was stirred for 3 hours. After an addition of water, the product was extracted with chloroform and dried over anhydrous sodium sulfate. Then, chloroform was distilled off under reduced pressure, and the product was purified by column chromatography to obtain 0.53 g (yield: 32.4%, melting point: 151.5.degree.-154.5.degree. C.) of 2-(2-methyl-3-methoxymethyl-4-methylsulfonylbenzoyl)tetrahydrothiopyran-3-one.
[.sup.1 H-NMR .delta.value: ((CDCl.sub.3)) 2.gtoreq.3 ppm(6H, m), 2.4 ppm(3H, s), 3.15 ppm(3H, s), 3.45 ppm(3H, s), 4.9 ppm(2H, s), 7-8 ppm (2H)
Melting point: 151.5-154.4.degree. C.]
In a manner similar to the above reactions, compounds of the formula I of the present invention as identified in Tables 1 and 2 can be prepared. However, the present invention is not limited to such specific compounds.
The Compound Nos. in Tables 1 and 2 will be referred to in the subsequent Formulation Examples and Test Examples.
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 or diatomaceous earth, or a liquid carrier such as water, an alcohol (such as methanol or ethanol), an aromatic hydrocarbon (such as benzene, toluene or xylene), a chlorinated hydrocarbon, an ether, a ketone, an ester (such as ethyl acetate), or an acid amide (such as dimethylformamide). If desired, an emulsifier, a dispersing agent, a suspending agent, a penetrating agent, a spreader or a stabilizer may be added to prepare an optional formulation such as a liquid formulation, an emulsifiable concentrate, a wettable powder, a dust, a granule or a flowable. There is no particular restriction as to the content of the compound of the present invention as the active ingredient in such a formulation. However, the content is usually preferably within a range of from 0.10 to 90.0% by weight. Further, if desired, other herbicides, various insecticides, bacteriocides, plant growth regulating agents or synergism agents, may be combined at the time of the preparation of the formulations or at the time of the application. As such compounds to be combined, there may be mentioned, for instance, compounds disclosed in Farm Chemicals Handbook, the 75th Edition (1989).
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 rail way 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 0.005 to 10 kg per hectare as the amount of the active ingredient.
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".
Liquid Formulation
Active ingredient: 5-75 parts, preferably 10-50 parts, more preferably 15-40 parts,
Liquid carrier: 95-25 parts, preferably 88-30 parts, more preferably 82-40 parts,
Surfactant: 1.varies.30 parts, preferably 2-20 parts.
Emulsifiable Concentrate
Active ingredient: 1-50 parts, preferably 5-45 parts, more preferably 10-40 parts,
Surfactant: 1-30 parts, preferably 2-25 parts, more preferably 3-20 parts,
Liquid carrier: 20-95 parts, preferably 30-93 parts, more preferably 57-85 parts,
Dust
Active ingredient: 0.5-10 parts, preferably 15-40 parts,
Solid carrier: 95.9-90 parts.
Flowable
Active ingredient: 5-75 parts, preferably 10-50 parts,
Water: 94-25 parts, preferably 90-30 parts,
Surfactant: 1-30 parts, preferably 2-20 parts.
Wettable Powder
Active ingredient: 2.5-90 parts, preferably 10-80 parts, more preferably 20-75 parts,
Surfactant: 0.5-20 parts, preferably 1-15 parts, more preferably 2-10 parts,
Liquid carrier: 5-90 parts, preferably, 7.5-88 parts, more preferably 16-56 parts.
Granule
Active ingredient: 0.1-30 parts,
Solid carrier: 995.-70 parts.
The liquid formulation and the emulsifiable concentrate are prepared by dissolving the active ingredient in a liquid carrier containing a surfactant. The wettable powder is prepared by mixing a surfactant, a solid carrier and the active ingredient, followed by pulverization.
The dust is prepared by mixing a surfactant, a solid carrier and the active ingredient, if necessary, followed pulverization.
The flowable is prepared by suspending and dispersing the active ingredient in an aqueous solution containing a surfactant. The granule is prepared by mixing the active ingredient with an ajuvant.
FORMULATION EXAMPLE 1
Wettable Powder
______________________________________Compound No. 1 of the present invention 50 partsZeeklite PFP (tradename for a kaolin-type 43 partsclay, manufactured by Toho ChemicalCo., Ltd.)Sorpol 5039 (tradename for a mixture of a 5 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalCo., 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. In its use, the above wettable powder is diluted with water from 10 to 10,000 times and applied so that the active ingredient will be from 0.005 to 10 kg per hectare.
FORMULATION EXAMPLE 2
Emulsifiable Concentrate
______________________________________Compound No. 2 of the present invention 10 partsXylene 70 partsN,N-dimethylformamide 10 partsSorpol 2680 (tradename for a mixture of a 10 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalCo., Ltd.)______________________________________
The above ingredients are homogeneously mixed to form an emulsifiable concentrate. In its use, the above emulsifiable concentrate is diluted with water from 10 to 10,000 times and applied so that the active ingredient will be from 0.005 to 10 kg per hectare.
FORMULATION EXAMPLE 3
Flowable
______________________________________Compound No. 3 of the present invention 25 partsSorpol 3353 (tradename for a nonionic surfactant, 10 partsmanufactured by Toho Chemical Co., Ltd.)Runox 1000C (tradename for an anionic 0.5 partsurfactant, manufactured by Toho ChemicalCo., Ltd.)1% Xanthan gum aqueous solution (natural polymer) 20 partsWater 44.5 parts______________________________________
Sorpol 3353, Runox 1000C and the 1% Xanthan gum aqueous solution were uniformly dissolved in water, then Compound No. 3 of the present invention was added, and the mixture was thoroughly stirred. Then, the mixture was subjected to wet pulverization by a sand mil to obtain a flowable. In its use, the above flowable is diluted from 10 to 10,000 times and applied so that the active ingredient will be 0.005 to 10 kg per hectare.
FORMULATION EXAMPLE 4
Liquid Formulation
______________________________________Compound No. 7 of the present invention 20 partsSorpol W-150 (tradename for a nonionic 10 partsurfactant, manufactured by Toho ChemicalCo., Ltd.)Water 70 parts______________________________________
The above ingredients are uniformly mixed to form a liquid formulation. In its use, the above liquid formulation is diluted from 10 to 10,000 times and applied so that the active ingredient will be from 0.005 to 10 kg per hectare.
FORMULATION EXAMPLE 5
Liquid Formulation
______________________________________Compound No. 17 of the present invention 30 partsNippol (tradename for a nonionic 10 partssurfactant, manufactured by NissanChemical Industries Ltd.)Water 60 parts______________________________________
The above ingredients are homogeneously mixed to obtain a liquid formulation. In its use, the above liquid formulation is diluted from 10 to 10,000 times and applied to so that the active ingredient will be from 0,005 to 10 kg per hectare.
FORMULATION EXAMPLE 6
Wettable Powder
______________________________________Compound No. 1736 of the present invention 20 partsZeeklite PFP (tradename for a kaolin-type 73 partsclay, manufactured by Zeeklite Industries,Co., Ltd.)Sorpol 5039 (tradename for a mixture of a 5 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalCo., 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 7
Wettable Powder
______________________________________Compound No. 29 of the present invention 30 partsZeeklite PFP (tradename for a kaolin-type 63 partsclay, manufactured by Zeeklite Industries,Co., Ltd.)Sorpol 5039 (tradename for a mixture of a 5 partsnonionic surfactant and an anionicsurfactant, manufactured by Toho ChemicalCo., 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 8
Granule
______________________________________Compound No. 32 of the present invention 5 partsBentonite 54 partsTalc 40 partsCalcium lignin sulfonate 1 part______________________________________
The above ingredients were homogenously 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 its use, the above granule is applied so that the active ingredient will be from 0.005 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 30 cm, a width of 22 cm and a depth of 6 cm was filled with a sterilized diluvium soil, and seeds of Echinochloa crus-galli, Digitaria adscendens, Cyperus microiria, Solanum nigrum, Galinsoga ciliata, Rorripa indica, Zea mays and Triticum aestivum were sown, and the soil was covered thereon in the thickness of about 1.5 cm, and then a herbicide solution was applied 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 liquid formulation, the wettable powder, the emulsifiable concentrate or the flowable as described in the foregoing Formulation Examples with water and applied onto the entire soil surface by means of a small spray. Three weeks after the application of the herbicidal solution, the herbicidal effects against each weed were determined on the basis of the following standard ratings.
Standard Ratings
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 growth above the soil surface of the treated area
N: Weight of the weed growth above the soil surface of the non-treated area
The results thereby obtained are shown in Table 3.
TEST EXAMPLE 2
Test 1 on the Herbicidal Effects in Foliage Treatment
A plastic box having a length of 30 cm, a width of 22 cm and a depth of 6 cm was filled with a sterilized diluvium soil, and seeds of Echinochloa crus-galli, Digitaria adscendens, Cyperus microiria, Solanum nigrum, Galinsoga ciliata, Rorripa indica, Zea mays and Triticum aestivum were spot-wisely sown, and the soil was covered thereon in a thickness of about 1.5 cm. When the various weeds and crop plant grew to the 2 to 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 liquid formulation, the wettable powder, the emulsifiable concentrate or the flowable as described in the above Formulation Examples with water and applied onto the entire surface of the foliages of the weeds and the crop plant 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 determine on the basis of the standard ratings described in Test Example 1. The results are shown in Table 4.
In the following Tables 1 and 2, Me means a methyl group, Et means an ethyl group and Ph means a phenyl group.
In Tables 3 and 4, the following abbreviations are used.
EC: Echinochloa crus-galli (barnyardgrass)
Dose: Dose of active ingredient (kg/ha)
DI: Digitaria adscendens (large crabgrass)
CY: Cyperus microiria (flatsedge)
SO: solanum nigrum (black nigthshade)
GA: Galinsoga ciliate (hairy galinsoga)
RO: Rorripa indica
ZE: Zea mays (corn)
TR: Triticum aestivum (wheat)
TABLE 1__________________________________________________________________________ ##STR16##Compound No. of Chracteristicpresent invention (R).sub.m L X Y Z (Physical property)__________________________________________________________________________1 -- 0 Cl H Cl Brown liquid n.sub.D.sup.25 1.62882 -- 0 Cl H SO.sub.2 Me Slightly yellow crystal m.p. 111.about.113.degree. C.3 -- 0 Cl H NO.sub.2 Reddish brown crystal m.p. 59.5.about.62.5.degree. C.4 -- 0 Cl H OMe5 -- 0 Cl H Me6 -- 0 Cl H Br7 -- 0 Cl H F Yellowish brown liquid8 -- 0 Cl H SMe9 -- 0 Cl H S(O)Me10 -- 0 Cl H CF.sub.311 -- 0 Cl H CN12 -- 0 Cl Cl Cl13 -- 0 Cl Cl OMe14 -- 0 Cl Cl SMe15 -- 0 Cl Cl SO.sub.2 Me16 -- 0 Cl Me Cl Yellow liquid n.sub.D.sup.20 1.631217 -- 0 Cl Me SO.sub.2 Me Yellow crystal m.p. 141.5.about.144.degree. C.18 -- 0 Cl OMe Cl19 -- 0 Cl OMe Br20 -- 0 Cl OMe SO.sub.2 Me21 -- 0 Cl OEt Br22 -- 0 Br H OMe23 -- 0 F H F24 -- 0 I I I25 -- 0 Me H CN26 -- 0 Me H Me27 -- 0 Me H OMe28 -- 0 Me Cl Cl29 -- 0 Me CO.sub.2 Et SO.sub.2 Me Yellow semicrystal30 -- 0 Me CH.sub.2 OMe SO.sub.2 Me Slightly yellow crystal m.p. 151.5.about.154.5.degree. C.31 -- 0 Me CO.sub.2 Me SO.sub.2 Me32 -- 0 NO.sub.2 H Cl Reddish brown crystal m.p. 113.about.116.degree. C.33 -- 0 NO.sub.2 H Br34 -- 0 NO.sub.2 H F35 -- 0 NO.sub.2 H CN36 -- 0 NO.sub.2 H SMe37 -- 0 NO.sub.2 H CF.sub.3 Slightly yellow crystal m.p. 104.about.106.degree. C.38 -- 0 NO.sub.2 OMe Cl39 -- 0 NO.sub.2 OMe CF.sub.340 -- 0 CF.sub.3 H Cl41 -- 0 CF.sub.3 H Br42 -- 0 CF.sub.3 H SMe43 -- 0 CF.sub.3 H CF.sub.344 -- 0 OMe H Cl45 -- 0 OMe H OMe Slightly yellow crystal m.p. 101.about.104.degree. C.46 -- 1 Cl H Cl47 -- 1 Cl H SO.sub.2 Me48 -- 1 Cl H NO.sub.249 -- 1 Cl H OMe50 -- 1 Cl H Me51 -- 1 Cl H Br52 -- 1 Cl H F53 -- 1 Cl H SMe54 -- 1 Cl H S(O)Me55 -- 1 Cl H CF.sub.356 -- 1 Cl H CN57 -- 1 Cl Cl Cl58 -- 1 Cl Cl OMe59 -- 1 Cl Cl SMe60 -- 1 Cl Cl SO.sub.2 Me61 -- 1 Cl Me Cl62 -- 1 Cl Me SO.sub.2 Me63 -- 1 Cl OMe Cl64 -- 1 Cl OMe Br65 -- 1 Cl OMe SO.sub.2 Me66 -- 1 Cl OEt Br67 -- 1 Br H OMe68 -- 1 F H F69 -- 1 I I I70 -- 1 Me H CN71 -- 1 Me H Me72 -- 1 Me H OMe73 -- 1 Me Cl Cl74 -- 1 Me CO.sub. 2 Me SO.sub.2 Me75 -- 1 Me CH.sub.2 OMe SO.sub.2 Me76 -- 1 Me CH(Me)OMe SO.sub.2 Me77 -- 1 NO.sub.2 H Cl78 -- 1 NO.sub.2 H Br79 -- 1 NO.sub.2 H F80 -- 1 NO.sub.2 H CN81 -- 1 NO.sub.2 H SMe82 -- 1 NO.sub.2 H CF.sub.383 -- 1 NO.sub.2 OMe Cl84 -- 1 NO.sub.2 OMe CF.sub.385 -- 1 CF.sub.3 H Cl86 -- 1 CF.sub.3 H Br87 -- 1 CF.sub.3 H SMe88 -- 1 CF.sub.3 H CF.sub.389 -- 1 OMe H Cl90 -- 1 OMe H OMe91 -- 2 Cl H Cl92 -- 2 Cl H SO.sub.2 Me93 -- 2 Cl H NO.sub.294 -- 2 Cl H OMe95 -- 2 Cl H Me96 -- 2 Cl H Br97 -- 2 Cl H F98 -- 2 Cl H SMe99 -- 2 Cl H S(O)Me100 -- 2 Cl H CF.sub.3101 -- 2 Cl H CN102 -- 2 Cl Cl Cl103 -- 2 Cl Cl OMe104 -- 2 Cl Cl SMe105 -- 2 Cl Cl SO.sub.2 Me106 -- 2 Cl Me Cl107 -- 2 Cl Me SO.sub.2 Me108 -- 2 Cl OMe Cl109 -- 2 Cl OMe Br110 -- 2 Cl OMe SO.sub.2 Me111 -- 2 Cl OEt Br112 -- 2 Br H OMe113 -- 2 F H F114 -- 2 I I I115 -- 2 Me H CN116 -- 2 Me H Me117 -- 2 Me H OMe118 -- 2 Me Cl Cl119 -- 2 Me CO.sub.2 Me SO.sub.2 Me120 -- 2 Me CH.sub.2 OMe SO.sub.2 Me121 -- 2 Me CH(Me)OMe SO.sub.2 Me122 -- 2 NO.sub.2 H Cl123 -- 2 NO.sub.2 H Br124 -- 2 NO.sub.2 H F125 -- 2 NO.sub.2 H CN126 -- 2 NO.sub.2 H SMe127 -- 2 NO.sub.2 H CF.sub.3128 -- 2 NO.sub.2 OMe Cl129 -- 2 NO.sub.2 OMe CF.sub.3130 -- 2 CF.sub.3 H Cl131 -- 2 CF.sub.3 H Br132 -- 2 CF.sub.3 H SMe133 -- 2 CF.sub.3 H CF.sub.3134 -- 2 OMe H Cl135 -- 2 OMe H OMe136 4-Me 0 Cl H Cl137 4-Me 0 Cl H SO.sub.2 Me138 4-Me 0 Cl H NO.sub.2139 4-Me 0 Cl H OMe140 4-Me 0 Cl H Me141 4-Me 0 Cl H Br142 4-Me 0 Cl H F143 4-Me 0 Cl H SMe144 4-Me 0 Cl H S(O)Me145 4-Me 0 Cl H CF.sub.3146 4-Me 0 Cl H CN147 4-Me 0 Cl Cl Cl148 4-Me 0 Cl Cl OMe149 4-Me 0 Cl Cl SMe150 4-Me 0 Cl Cl SO.sub.2 Me151 4-Me 0 Cl Me Cl152 4-Me 0 Cl Me SO.sub.2 Me153 4-Me 0 Cl OMe Cl154 4-Me 0 Cl OMe Br155 4-Me 0 Cl OMe SO.sub.2 Me156 4-Me 0 Cl OEt Br157 4-Me 0 Br H OMe158 4-Me 0 F H F159 4-Me 0 I I I160 4-Me 0 Me H CN161 4-Me 0 Me H Me162 4-Me 0 Me H OMe163 4-Me 0 Me Cl Cl164 4-Me 0 Me CO.sub.2 Me SO.sub.2 Me165 4-Me 0 Me CH.sub.2 OMe SO.sub.2 Me166 4-Me 0 Me CH(Me)OMe SO.sub.2 Me167 4-Me 0 NO.sub.2 H Cl168 4-Me 0 NO.sub.2 H Br169 4-Me 0 NO.sub.2 H F170 4-Me 0 NO.sub.2 H CN171 4-Me 0 NO.sub.2 H SMe172 4-Me 0 NO.sub.2 H CF.sub.3173 4-Me 0 NO.sub.2 OMe Cl174 4-Me 0 NO.sub.2 OMe CF.sub.3175 4-Me 0 CF.sub.3 H Cl176 4-Me 0 CF.sub.3 H Br177 4-Me 0 CF.sub.3 H SMe178 4-Me 0 CF.sub.3 H CF.sub.3179 4-Me 0 OMe H Cl180 4-Me 0 OMe H OMe181 4-Me 1 Cl H Cl182 4-Me 1 Cl H SO.sub.2 Me183 4-Me 1 Cl H NO.sub.2184 4-Me 1 Cl H OMe185 4-Me 1 Cl H Me186 4-Me 1 Cl H Br187 4-Me 1 Cl H F188 4-Me 1 Cl H SMe189 4-Me 1 Cl H S(O)Me190 4-Me 1 Cl H CF.sub.3191 4-Me 1 Cl H CN192 4-Me 1 Cl Cl Cl193 4-Me 1 Cl Cl OMe194 4-Me 1 Cl Cl SMe195 4-Me 1 Cl Cl SO.sub.2 Me196 4-Me 1 Cl Me Cl197 4-Me 1 Cl Me SO.sub.2 Me198 4-Me 1 Cl OMe Cl199 4-Me 1 Cl OMe Br200 4-Me 1 Cl OMe SO.sub.2 Me201 4-Me 1 Cl OEt Br202 4-Me 1 Br H OMe203 4-Me 1 F H F204 4-Me 1 I I I205 4-Me 1 Me H CN206 4-Me 1 Me H Me207 4-Me 1 Me H OMe208 4-Me 1 Me Cl Cl209 4-Me 1 Me CO.sub.2 Me SO.sub.2 Me210 4-Me 1 Me CH.sub.2 OMe SO.sub.2 Me211 4-Me 1 Me CH(Me)OMe SO.sub.2 Me212 4-Me 1 NO.sub.2 H Cl213 4-Me 1 NO.sub.2 H Br214 4-Me 1 NO.sub.2 H F215 4-Me 1 NO.sub.2 H CN216 4-Me 1 NO.sub.2 H SMe217 4-Me 1 NO.sub.2 H CF.sub.3218 4-Me 1 NO.sub.2 OMe Cl219 4-Me 1 NO.sub.2 OMe CF.sub.3220 4-Me 1 CF.sub.3 H Cl221 4-Me 1 CF.sub.3 H Br222 4-Me 1 CF.sub.3 H SMe223 4-Me 1 CF.sub.3 H CF.sub.3224 4-Me 1 OMe H Cl225 4-Me 1 OMe H OMe226 4-Me 2 Cl H Cl227 4-Me 2 Cl H SO.sub.2 Me228 4-Me 2 Cl H NO.sub.2229 4-Me 2 Cl H OMe230 4-Me 2 Cl H Me231 4-Me 2 Cl H Br232 4-Me 2 Cl H F233 4-Me 2 Cl H SMe234 4-Me 2 Cl H S(O)Me235 4-Me 2 Cl H CF.sub.3236 4-Me 2 Cl H CN237 4-Me 2 Cl Cl Cl238 4-Me 2 Cl Cl OMe239 4-Me 2 Cl Cl SMe240 4-Me 2 Cl Cl SO.sub.2 Me241 4-Me 2 Cl Me Cl242 4-Me 2 Cl Me SO.sub.2 Me243 4-Me 2 Cl OMe Cl244 4-Me 2 Cl OMe Br245 4-Me 2 Cl OMe SO.sub.2 Me246 4-Me 2 Cl OEt Br247 4-Me 2 Br H OMe248 4-Me 2 F H F249 4-Me I I I250 4-Me 2 Me H CN251 4-Me 2 Me H Me252 4-Me 2 Me H OMe253 4-Me 2 Me Cl Cl254 4-Me 2 Me CO.sub.2 Me SO.sub.2 Me255 4-Me 2 Me CH.sub.2 OMe SO.sub.2 Me256 4-Me 2 Me CH(Me)OMe SO.sub.2 Me257 4-Me 2 NO.sub.2 H Cl258 4-Me 2 NO.sub.2 H Br259 4-Me 2 NO.sub.2 H F260 4-Me 2 NO.sub.2 H CN261 4-Me 2 NO.sub.2 H SMe262 4-Me 2 NO.sub.2 H CF.sub.3263 4-Me 2 NO.sub.2 OMe Cl264 4-Me 2 NO.sub.2 OMe CF.sub.3265 4-Me 2 CF.sub.3 H Cl266 4-Me 2 CF.sub.3 H Br267 4-Me 2 CF.sub.3 H SMe268 4-Me 2 CF.sub.3 H CF.sub.3269 4-Me 2 OMe H Cl270 4-Me 2 OMe H OMe271 5-Me 0 Cl H Cl272 5-Me 0 Cl H SO.sub.2 Me273 5-Me 0 Cl H NO.sub.2274 5-Me 0 Cl H OMe275 5-Me 0 Cl H Me276 5-Me 0 Cl H Br277 5-Me 0 Cl H F278 5-Me 0 Cl H SMe279 5-Me 0 Cl H S(O)Me280 5-Me 0 Cl H CF.sub.3281 5-Me 0 Cl H CN282 5-Me 0 Cl Cl Cl283 5-Me 0 Cl Cl OMe284 5-Me 0 Cl Cl SMe285 5-Me 0 Cl Cl SO.sub.2 Me286 5-Me 0 Cl Me Cl287 5-Me 0 Cl Me SO.sub.2 Me288 5-Me 0 Cl OMe Cl289 5-Me 0 Cl OMe Br290 5-Me 0 Cl OMe SO.sub.2 Me291 5-Me 0 Cl OEt Br292 5-Me 0 Br H OMe293 5-Me 0 F H F294 5-Me 0 I I I295 5-Me 0 Me H CN296 5-Me 0 Me H Me297 5-Me 0 Me H OMe298 5-Me 0 Me Cl Cl299 5-Me 0 Me CO.sub.2 Me SO.sub.2 Me300 5-Me 0 Me CH.sub.2 OMe SO.sub.2 Me301 5-Me 0 Me CH(Me)OMe SO.sub.2 Me302 5-Me 0 NO.sub.2 H Cl303 5-Me 0 NO.sub.2 H Br304 5-Me 0 NO.sub.2 H F305 5-Me 0 NO.sub.2 H CN306 5-Me 0 NO.sub.2 H SMe307 5-Me 0 NO.sub.2 H CF.sub.3308 5-Me 0 NO.sub.2 OMe Cl309 5-Me 0 NO.sub.2 OMe CF.sub.3310 5-Me O CF.sub.3 H Cl311 5-Me 0 CF.sub.3 H Br312 5-Me 0 CF.sub.3 H SMe313 5-Me 0 CF.sub.3 H CF.sub.3314 5-Me 0 OMe H Cl315 5-Me 0 OMe H OMe316 5-Me 1 Cl H Cl317 5-Me 1 Cl H SO.sub.2 Me318 5-Me 1 Cl H NO.sub.2319 5-Me 1 Cl H OMe320 5-Me 1 Cl H Me321 5-Me 1 Cl H Br322 5-Me 1 Cl H F323 5-Me 1 Cl H SMe324 5-Me 1 Cl H S(O)Me325 5-Me 1 Cl H CF.sub.3326 5-Me 1 Cl H CN327 5-Me 1 Cl Cl Cl328 5-Me 1 Cl Cl OMe329 5-Me 1 Cl Cl SMe330 5-Me 1 Cl Cl SO.sub.2 Me331 5-Me 1 Cl Me Cl332 5-Me 1 Cl Me SO.sub.2 Me333 5-Me 1 Cl OMe Cl334 5-Me 1 Cl OMe Br335 5-Me 1 Cl OMe SO.sub.2 Me336 5-Me 1 Cl OEt Br337 5-Me 1 Br H OMe338 5-Me 1 F H F339 5-Me 1 I I I340 5-Me 1 Me H CN341 5-Me 1 Me H Me342 5-Me 1 Me H OMe343 5-Me 1 Me Cl Cl344 5-Me 1 Me CO.sub.2 Me SO.sub.2 Me345 5-Me 1 Me CH.sub.2 OMe SO.sub.2 Me346 5-Me 1 Me CH(Me)OMe SO.sub.2 Me347 5-Me 1 NO.sub.2 H Cl348 5-Me 1 NO.sub.2 H Br349 5-Me 1 NO.sub.2 H F350 5-Me 1 NO.sub.2 H CN351 5-Me 1 NO.sub.2 H SMe352 5-Me 1 NO.sub.2 H CF.sub.3353 5-Me 1 NO.sub.2 OMe Cl354 5-Me 1 NO.sub.2 OMe CF.sub.3355 5-Me 1 CF.sub.3 H Cl356 5-Me 1 CF.sub.3 H Br357 5-Me 1 CF.sub.3 H SMe358 5-Me 1 CF.sub.3 H CF.sub.3359 5-Me 1 OMe H Cl360 5-Me 1 OMe H OMe361 5-Me 2 Cl H Cl362 5-Me 2 Cl H SO.sub.2 Me363 5-Me 2 Cl H NO.sub.2364 5-Me 2 Cl H OMe365 5-Me 2 Cl H Me366 5-Me 2 Cl H Br367 5-Me 2 Cl H F368 5-Me 2 Cl H SMe369 5-Me 2 Cl H S(O)Me370 5-Me 2 Cl H CF.sub.3371 5-Me 2 Cl H CN372 5-Me 2 Cl Cl Cl373 5-Me 2 Cl Cl OMe374 5-Me 2 Cl Cl SMe375 5-Me 2 Cl Cl SO.sub.2 Me376 5-Me 2 Cl Me Cl377 5-Me 2 Cl Me SO.sub.2 Me378 5-Me 2 Cl OMe Cl379 5-Me 2 Cl OMe Br380 5-Me 2 Cl OMe SO.sub.2 Me381 5-Me 2 Cl OEt Br382 5-Me 2 Br H OMe383 5-Me 2 F H F384 5-Me 2 I I I385 5-Me 2 Me H CN386 5-Me 2 Me H Me387 5-Me 2 Me H OMe388 5-Me 2 Me Cl Cl389 5-Me 2 Me CO.sub.2 Me SO.sub.2 Me390 5-Me 2 Me CH.sub.2 OMe SO.sub.2 Me391 5-Me 2 Me CH(Me)OMe SO.sub.2 Me392 5-Me 2 NO.sub.2 H Cl393 5-Me 2 NO.sub.2 H Br394 5-Me 2 NO.sub.2 H F395 5-Me 2 NO.sub.2 H CN396 5-Me 2 NO.sub.2 H SMe397 5-Me 2 NO.sub.2 H CF.sub.3398 5-Me 2 NO.sub.2 OMe Cl399 5-Me 2 NO.sub.2 OMe CF.sub.3400 5-Me 2 CF.sub.3 H Cl401 5-Me 2 CF.sub.3 H Br402 5-Me 2 CF.sub.3 H SMe403 5-Me 2 CF.sub.3 H CF.sub.3404 5-Me 2 OMe H Cl405 5-Me 2 OMe H OMe406 6-Me 0 Cl H Cl Slightly green liquid n.sub.D.sup.20 1.6219407 6-Me 0 Cl H SO.sub.2 Me408 6-Me 0 Cl H NO.sub.2409 6-Me 0 Cl H OMe410 6-Me 0 Cl H Me411 6-Me 0 Cl H Br412 6-Me 0 Cl H F413 6-Me 0 Cl H SMe414 6-Me 0 Cl H S(O)Me415 6-Me 0 Cl H CF.sub.3416 6-Me 0 Cl H CN417 6-Me 0 Cl Cl Cl418 6-Me 0 Cl Cl OMe419 6-Me 0 Cl Cl SMe420 6-Me 0 Cl Cl SO.sub.2 Me421 6-Me 0 Cl Me Cl Slightly yellow liquid n.sub.D.sup.20 1.6203422 6-Me 0 Cl Me SO.sub.2 Me423 6-Me 0 Cl OMe Cl424 6-Me 0 Cl OMe Br425 6-Me 0 Cl OMe SO.sub.2 Me426 6-Me 0 Cl OEt Br427 6-Me 0 Br H OMe428 6-Me 0 F H F429 6-Me 0 I I I430 6-Me 0 Me H CN431 6-Me 0 Me H Me432 6-Me 0 Me H OMe433 6-Me 0 Me Cl Cl434 6-Me 0 Me CO.sub.2 Me SO.sub.2 Me435 6-Me 0 Me CH.sub.2 OMe SO.sub.2 Me436 6-Me 0 Me CH(Me)OMe SO.sub.2 Me437 6-Me 0 NO.sub.2 H Cl438 6-Me 0 NO.sub.2 H Br439 6-Me 0 NO.sub.2 H F440 6-Me 0 NO.sub.2 H CN441 6-Me 0 NO.sub.2 H SMe442 6-Me 0 NO.sub.2 H CF.sub.3 Slightly yellow crystal m.p. 88.about.91.degree. C.443 6-Me 0 NO.sub.2 OMe Cl444 6-Me 0 NO.sub.2 OMe CF.sub.3445 6-Me 0 CF.sub.3 H Cl446 6-Me 0 CF.sub.3 H Br447 6-Me 0 CF.sub.3 H SMe448 6-Me 0 CF.sub.3 H CF.sub.3449 6-Me 0 OMe H Cl450 6-Me 0 OMe H OMe451 6-Me 1 Cl H Cl452 6-Me 1 Cl H SO.sub.2 Me453 6-Me 1 Cl H NO.sub.2454 6-Me 1 Cl H OMe455 6-Me 1 Cl H Me456 6-Me 1 Cl H Br457 6-Me 1 Cl H F458 6-Me 1 Cl H SMe459 6-Me 1 Cl H S(O)Me460 6-Me 1 Cl H CF.sub.3461 6-Me 1 Cl H CN462 6-Me 1 Cl Cl Cl463 6-Me 1 Cl Cl OMe464 6-Me 1 Cl Cl SMe465 6-Me 1 Cl Cl SO.sub.2 Me466 6-Me 1 Cl Me Cl467 6-Me 1 Cl Me SO.sub.2 Me468 6-Me 1 Cl OMe Cl469 6-Me 1 Cl OMe Br470 6-Me 1 Cl OMe SO.sub.2 Me471 6-Me 1 Cl OEt Br472 6-Me 1 Br H OMe473 6-Me 1 F H F474 6-Me 1 I I I475 6-Me 1 Me H CN476 6-Me 1 Me H Me477 6-Me 1 Me H OMe478 6-Me 1 Me Cl Cl479 6-Me 1 Me CO.sub.2 Me SO.sub.2 Me480 6-Me 1 Me CH.sub.2 OMe SO.sub.2 Me481 6-Me 1 Me CH(Me)OMe SO.sub.2 Me482 6-Me 1 NO.sub.2 H Cl483 6-Me 1 NO.sub.2 H Br484 6-Me 1 NO.sub.2 H F485 6-Me 1 NO.sub.2 H CN486 6-Me 1 NO.sub.2 H SMe487 6-Me 1 NO.sub.2 H CF.sub.3488 6-Me 1 NO.sub.2 OMe Cl489 6-Me 1 NO.sub.2 OMe CF.sub.3490 6-Me 1 CF.sub.3 H Cl491 6-Me 1 CF.sub.3 H Br492 6-Me 1 CF.sub.3 H SMe493 6-Me 1 CF.sub.3 H CF.sub.3494 6-Me 1 OMe H Cl495 6-Me 1 OMe H OMe496 6-Me 2 Cl H Cl497 6-Me 2 Cl H SO.sub.2 Me498 6-Me 2 Cl H NO.sub.2499 6-Me 2 Cl H OMe500 6-Me 2 Cl H Me501 6-Me 2 Cl H Br502 6-Me 2 Cl H F503 6-Me 2 Cl H SMe504 6-Me 2 Cl H S(O)Me505 6-Me 2 Cl H CF.sub.3506 6-Me 2 Cl H CN507 6-Me 2 Cl Cl Cl508 6-Me 2 Cl Cl OMe509 6-Me 2 Cl Cl SMe510 6-Me 2 Cl Cl SO.sub.2 Me511 6-Me 2 Cl Me Cl512 6-Me 2 Cl Me SO.sub.2 Me513 6-Me 2 Cl OMe Cl514 6-Me 2 Cl OMe Br515 6-Me 2 Cl OMe SO.sub.2 Me516 6-Me 2 Cl OEt Br517 6-Me 2 Br H OMe518 6-Me 2 F H F519 6-Me 2 I I I520 6-Me 2 Me H CN521 6-Me 2 Me H Me522 6-Me 2 Me H OMe523 6-Me 2 Me Cl Cl524 6-Me 2 Me CO.sub.2 Me SO.sub.2 Me525 6-Me 2 Me CH.sub.2 OMe SO.sub.2 Me526 6-Me 2 Me CH(Me)OMe SO.sub.2 Me527 6-Me 2 NO.sub.2 H Cl528 6-Me 2 NO.sub.2 H Br529 6-Me 2 NO.sub.2 H F530 6-Me 2 NO.sub. 2 H CN531 6-Me 2 NO.sub.2 H SMe532 6-Me 2 NO.sub.2 H CF.sub.3533 6-Me 2 NO.sub.2 OMe Cl534 6-Me 2 NO.sub.2 OMe CF.sub.3535 6-Me 2 CF.sub.3 H Cl536 6-Me 2 CF.sub.3 H Br537 6-Me 2 CF.sub.3 H SMe538 6-Me 2 CF.sub.3 H CF.sub.3539 6-Me 2 OMe H Cl540 6-Me 2 OMe H OMe541 4.4-diMe 0 Cl H Cl542 4.4-diMe 0 Cl H SO.sub.2 Me543 4.4-diMe 0 Cl H NO.sub.2544 4.4-diMe 0 Cl H OMe545 4.4-diMe 0 Cl H Me546 4.4-diMe 0 Cl H Br547 4.4-diMe 0 Cl H F548 4.4-diMe O Cl H SMe549 4.4-diMe 0 Cl H S(O)Me550 4.4-diMe 0 Cl H CF.sub.3551 4.4-diMe 0 Cl H CN552 4.4-diMe 0 Cl Cl Cl553 4.4-diMe 0 Cl Cl OMe554 4.4-diMe 0 Cl Cl SMe555 4.4-diMe 0 Cl Cl SO.sub.2 Me556 4.4-diMe 0 Cl Me Cl557 4.4-diMe 0 Cl Me SO.sub.2 Me558 4.4-diMe 0 Cl OMe Cl559 4.4-diMe 0 Cl OMe Br560 4.4-diMe 0 Cl OMe SO.sub.2 Me561 4.4-diMe 0 Cl OEt Br562 4.4-diMe 0 Br H OMe563 4.4-diMe 0 F H F564 4.4-diMe 0 I I I565 4.4-diMe 0 Me H CN566 4.4-diMe 0 Me H Me567 4.4-diMe 0 Me H OMe568 4.4-diMe 0 Me Cl Cl569 4.4-diMe 0 Me CO.sub.2 Me SO.sub.2 Me570 4.4-diMe 0 Me CH.sub.2 OMe SO.sub.2 Me571 4.4-diMe 0 Me CH(Me)OMe SO.sub.2 Me572 4.4-diMe 0 NO.sub.2 H Cl573 4.4-diMe 0 NO.sub.2 H Br574 4.4-diMe 0 NO.sub.2 H F575 4.4-diMe 0 NO.sub.2 H CN576 4.4-diMe 0 NO.sub.2 H SMe577 4.4-diMe 0 NO.sub.2 H CF.sub.3578 4.4-diMe 0 NO.sub.2 OMe Cl579 4.4-diMe 0 NO.sub.2 OMe CF.sub.3580 4.4-diMe 0 CF.sub.3 H Cl581 4.4-diMe 0 CF.sub.3 H Br582 4.4-diMe 0 CF.sub.3 H SMe583 4.4-diMe 0 CF.sub.3 H CF.sub.3584 4.4-diMe 0 OMe H Cl585 4.4-diMe 0 OMe H OMe586 4.4-diMe 1 Cl H Cl587 4.4-diMe 1 Cl H SO.sub.2 Me588 4.4-diMe 1 Cl H NO.sub.2589 4.4-diMe 1 Cl H OMe590 4.4-diMe 1 Cl H Me591 4.4-diMe 1 Cl H Br592 4.4-diMe 1 Cl H F593 4.4-diMe 1 Cl H SMe594 4.4-diMe 1 Cl H S(O)Me595 4.4-diMe 1 Cl H CF.sub.3596 4.4-diMe 1 Cl H CN597 4.4-diMe 1 Cl Cl Cl598 4.4-diMe 1 Cl Cl OMe599 4.4-diMe 1 Cl Cl SMe600 4.4-diMe 1 Cl Cl SO.sub.2 Me601 4.4-diMe 1 Cl Me Cl602 4.4-diMe 1 Cl Me SO.sub.2 Me603 4.4-diMe 1 Cl OMe Cl604 4.4-diMe 1 Cl OMe Br605 4.4-diMe 1 Cl OMe SO.sub.2 Me606 4.4-diMe 1 Cl OEt Br607 4.4-diMe 1 Br H OMe608 4.4-diMe 1 F H F609 4.4-diMe 1 I I I610 4.4-diMe 1 Me H CN611 4.4-diMe 1 Me H Me612 4.4-diMe 1 Me H OMe613 4.4-diMe 1 Me Cl Cl614 4.4-diMe 1 Me CO.sub.2 Me SO.sub.2 Me615 4.4-diMe 1 Me CH.sub.2 OMe SO.sub.2 Me616 4.4-diMe 1 Me CH(Me)OMe SO.sub.2 Me617 4.4-diMe 1 NO.sub.2 H Cl618 4.4-diMe 1 NO.sub.2 H Br619 4.4-diMe 1 NO.sub.2 H F620 4.4-diMe 1 NO.sub.2 H CN621 4.4-diMe 1 NO.sub.2 H SMe622 4.4-diMe 1 NO.sub.2 H CF.sub.3623 4.4-diMe 1 NO.sub.2 OMe Cl624 4.4-diMe 1 NO.sub.2 OMe CF.sub.3625 4.4-diMe 1 CF.sub.3 H Cl626 4.4-diMe 1 CF.sub.3 H Br627 4.4-diMe 1 CF.sub.3 H SMe628 4.4-diMe 1 CF.sub.3 H CF.sub.3629 4.4-diMe 1 OMe H Cl630 4.4-diMe 1 OMe H OMe631 4.4-diMe 2 Cl H Cl632 4.4-diMe 2 Cl H SO.sub.2 Me633 4.4-diMe 2 Cl H NO.sub.2634 4.4-diMe 2 Cl H OMe635 4.4-diMe 2 Cl H Me636 4.4-diMe 2 Cl H Br637 4.4-diMe 2 Cl H F638 4.4-diMe 2 Cl H SMe639 4.4-diMe 2 Cl H S(O)Me640 4.4-diMe 2 Cl H CF.sub.3641 4.4-diMe 2 Cl H CN642 4.4-diMe 2 Cl Cl Cl643 4.4-diMe 2 Cl Cl OMe644 4.4-diMe 2 Cl Cl SMe645 4.4-diMe 2 Cl Cl SO.sub.2 Me646 4.4-diMe 2 Cl Me Cl647 4.4-diMe 2 Cl Me SO.sub.2 Me648 4.4-diMe 2 Cl OMe Cl649 4.4-diMe 2 Cl OMe Br650 4.4-diMe 2 Cl OMe SO.sub.2 Me651 4.4-diMe 2 Cl OEt Br652 4.4-diMe 2 Br H OMe653 4.4-diMe 2 F H F654 4.4-diMe 2 I I I655 4.4-diMe 2 Me H CN656 4.4-diMe 2 Me H Me657 4.4-diMe 2 Me H OMe658 4.4-diMe 2 Me Cl Cl659 4.4-diMe 2 Me CO.sub.2 Me SO.sub.2 Me660 4.4-diMe 2 Me CH.sub.2 OMe SO.sub.2 Me661 4.4-diMe 2 Me CH(Me)OMe SO.sub.2 Me662 4.4-diMe 2 NO.sub.2 H Cl663 4.4-diMe 2 NO.sub.2 H Br664 4.4-diMe 2 NO.sub.2 H F665 4.4-diMe 2 NO.sub.2 H CN666 4.4-diMe 2 NO.sub.2 H SMe667 4.4-diMe 2 NO.sub.2 H CF.sub.3668 4.4-diMe 2 NO.sub.2 OMe Cl669 4.4-diMe 2 NO.sub.2 OMe CF.sub.3670 4.4-diMe 2 CF.sub.3 H Cl671 4.4-diMe 2 CF.sub.3 H Br672 4.4-diMe 2 CF.sub.3 H SMe673 4.4-diMe 2 CF.sub.3 H CF.sub.3674 4.4-diMe 2 OMe H Cl675 4.4-diMe 2 OMe H OMe676 5.5-diMe 0 Cl H Cl677 5.5-diMe 0 Cl H SO.sub.2 Me678 5.5-diMe 0 Cl H NO.sub.2679 5.5-diMe 0 Cl H OMe680 5.5-diMe 0 Cl H Me681 5.5-diMe 0 Cl H Br682 5.5-diMe 0 Cl H F683 5.5-diMe 0 Cl H SMe684 5.5-diMe 0 Cl H S(O)Me685 5.5-diMe 0 Cl H CF.sub.3686 5.5-diMe 0 Cl H CN687 5.5-diMe 0 Cl Cl Cl688 5.5-diMe 0 Cl Cl OMe689 5.5-diMe 0 Cl Cl SMe690 5.5-diMe 0 Cl Cl SO.sub.2 Me691 5.5-diMe 0 Cl Me Cl692 5.5-diMe 0 Cl Me SO.sub.2 Me693 5.5-diMe 0 Cl OMe Cl694 5.5-diMe 0 Cl OMe Br695 5.5-diMe 0 Cl OMe SO.sub.2 Me696 5.5-diMe 0 Cl OEt Br697 5.5-diMe 0 Br H OMe698 5.5-diMe 0 F H F699 5.5-diMe 0 I I I700 5.5-diMe 0 Me H CN701 5.5-diMe 0 Me H Me702 5.5-diMe 0 Me H OMe703 5.5-diMe 0 Me Cl Cl704 5.5-diMe 0 Me CO.sub.2 Me SO.sub.2 Me705 5.5-diMe 0 Me CH.sub.2 OMe SO.sub.2 Me706 5.5-diMe 0 Me CH(Me)OMe SO.sub.2 Me707 5.5-diMe 0 NO.sub.2 H Cl708 5.5-diMe 0 NO.sub.2 H Br709 5.5-diMe 0 NO.sub.2 H F710 5.5-diMe 0 NO.sub.2 H CN711 5.5-diMe 0 NO.sub.2 H SMe712 5.5-diMe 0 NO.sub.2 H CF.sub.3713 5.5-diMe 0 NO.sub.2 OMe Cl714 5.5-diMe 0 NO.sub.2 OMe CF.sub.3715 5.5-diMe 0 CF.sub.3 H Cl716 5.5-diMe 0 CF.sub.3 H Br717 5.5-diMe 0 CF.sub.3 H SMe718 5.5-diMe 0 CF.sub.3 H CF.sub.3719 5.5-diMe 0 OMe H Cl720 5.5-diMe 0 OMe H OMe721 5.5-diMe 1 Cl H Cl722 5.5-diMe 1 Cl H SO.sub.2 Me723 5.5-diMe 1 Cl H NO.sub.2724 5.5-diMe 1 Cl H OMe725 5.5-diMe 1 Cl H Me726 5.5-diMe 1 Cl H Br727 5.5-diMe 1 Cl H F728 5.5-diMe 1 Cl H SMe729 5.5-diMe 1 Cl H S(O)Me730 5.5-diMe 1 Cl H CF.sub.3731 5.5-diMe 1 Cl H CN732 5.5-diMe 1 Cl Cl Cl733 5.5-diMe 1 Cl Cl OMe734 5.5-diMe 1 Cl Cl SMe735 5.5-diMe 1 Cl Cl SO.sub.2 Me736 5.5-diMe 1 Cl Me Cl737 5.5-diMe 1 Cl Me SO.sub.2 Me738 5.5-diMe 1 Cl OMe Cl739 5.5-diMe 1 Cl OMe Br740 5.5-diMe 1 Cl OMe SO.sub.2 Me741 5.5-diMe 1 Cl OEt Br742 5.5-diMe 1 Br H OMe743 5.5-diMe 1 F H F744 5.5-diMe 1 I I I745 5.5-diMe 1 Me H CN746 5.5-diMe 1 Me H Me747 5.5-diMe 1 Me H OMe748 5.5-diMe 1 Me Cl Cl749 5.5-diMe 1 Me CO.sub.2 Me SO.sub.2 Me750 5.5-diMe 1 Me CH.sub.2 OMe SO.sub.2 Me751 5.5-diMe 1 Me CH(Me)OMe SO.sub.2 Me752 5.5-diMe 1 NO.sub.2 H Cl753 5.5-diMe 1 NO.sub.2 H Br754 5.5-diMe 1 NO.sub.2 H F755 5.5-diMe 1 NO.sub.2 H CN756 5.5-diMe 1 NO.sub.2 H SMe757 5.5-diMe 1 NO.sub.2 H CF.sub.3758 5.5-diMe 1 NO.sub.2 OMe Cl759 5.5-diMe 1 NO.sub.2 OMe CF.sub.3760 5.5-diMe 1 CF.sub.3 H Cl761 5.5-diMe 1 CF.sub.3 H Br762 5.5-diMe 1 CF.sub.3 H SMe763 5.5-diMe 1 CF.sub.3 H CF.sub.3764 5.5-diMe 1 OMe H Cl765 5.5-diMe 1 OMe H OMe766 5.5-diMe 2 Cl H Cl767 5.5-diMe 2 Cl H SO.sub.2 Me768 5.5-diMe 2 Cl H NO.sub.2769 5.5-diMe 2 Cl H OMe770 5.5-diMe 2 Cl H Me771 5.5-diMe 2 Cl H Br772 5.5-diMe 2 Cl H F773 5.5-diMe 2 Cl H SMe774 5.5-diMe 2 Cl H S(O)Me775 5.5-diMe 2 Cl H CF.sub.3776 5.5-diMe 2 Cl H CN777 5.5-diMe 2 Cl Cl Cl778 5.5-diMe 2 Cl Cl OMe779 5.5-diMe 2 Cl Cl SMe780 5.5-diMe 2 Cl Cl SO.sub.2 Me781 5.5-diMe 2 Cl Me Cl782 5.5-diMe 2 Cl Me SO.sub.2 Me783 5.5-diMe 2 Cl OMe Cl784 5.5-diMe 2 Cl OMe Br785 5.5-diMe 2 Cl OMe SO.sub.2 Me786 5.5-diMe 2 Cl OEt Br787 5.5-diMe 2 Br H OMe788 5.5-diMe 2 F H F789 5.5-diMe 2 I I I790 5.5-diMe 2 Me H CN791 5.5-diMe 2 Me H Me792 5.5-diMe 2 Me H OMe793 5.5-diMe 2 Me Cl Cl794 5.5-diMe 2 Me CO.sub.2 Me SO.sub.2 Me795 5.5-diMe 2 Me CH.sub.2 OMe SO.sub.2 Me796 5.5-diMe 2 Me CH(Me)OMe SO.sub.2 Me797 5.5-diMe 2 NO.sub.2 H Cl798 5.5-diMe 2 NO.sub.2 H Br799 5.5-diMe 2 NO.sub.2 H F800 5.5-diMe 2 NO.sub.2 H CN801 5.5-diMe 2 NO.sub.2 H SMe802 5.5-diMe 2 NO.sub.2 H CF.sub.3803 5.5-diMe 2 NO.sub.2 OMe Cl804 5.5-diMe 2 NO.sub.2 OMe CF.sub.3805 5.5-diMe 2 CF.sub.3 H Cl806 5.5-diMe 2 CF.sub.3 H Br807 5.5-diMe 2 CF.sub.3 H SMe808 5.5-diMe 2 CF.sub.3 H CF.sub.3809 5.5-diMe 2 OMe H Cl810 5.5-diMe 2 OMe H OMe811 6.6-diMe 0 Cl H Cl812 6.6-diMe 0 Cl H SO.sub.2 Me813 6.6-diMe 0 Cl H NO.sub.2814 6.6-diMe 0 Cl H OMe815 6.6-diMe 0 Cl H Me816 6.6-diMe 0 Cl H Br817 6.6-diMe 0 Cl H F818 6.6-diMe 0 Cl H SMe819 6.6-diMe 0 Cl H S(O)Me820 6.6-diMe 0 Cl H CF.sub.3821 6.6-diMe 0 Cl H CN822 6.6-diMe 0 Cl Cl Cl823 6.6-diMe 0 Cl Cl OMe824 6.6-diMe 0 Cl Cl SMe825 6.6-diMe 0 Cl Cl SO.sub.2 Me826 6.6-diMe 0 Cl Me Cl827 6.6-diMe 0 Cl Me SO.sub.2 Me828 6.6-diMe 0 Cl OMe Cl829 6.6-diMe 0 Cl OMe Br830 6.6-diMe 0 Cl OMe SO.sub.2 Me831 6.6-diMe 0 Cl OEt Br832 6.6-diMe 0 Br H OMe833 6.6-diMe 0 F H F834 6.6-diMe 0 I I I835 6.6-diMe 0 Me H CN836 6.6-diMe 0 Me H Me837 6.6-diMe 0 Me H OMe838 6.6-diMe 0 Me Cl Cl839 6.6-diMe 0 Me CO.sub.2 Me SO.sub.2 Me840 6.6-diMe 0 Me CH.sub.2 OMe SO.sub.2 Me841 6.6-diMe 0 Me CH(Me)OMe SO.sub.2 Me842 6.6-diMe 0 NO.sub.2 H Cl843 6.6-diMe 0 NO.sub.2 H Br844 6.6-diMe 0 NO.sub.2 H F845 6.6-diMe 0 NO.sub.2 H CN846 6.6-diMe 0 NO.sub.2 H SMe847 6.6-diMe 0 NO.sub.2 H CF.sub.3848 6.6-diMe 0 NO.sub.2 OMe Cl849 6.6-diMe 0 NO.sub.2 OMe CF.sub.3850 6.6-diMe 0 CF.sub.3 H Cl851 6.6-diMe 0 CF.sub.3 H Br852 6.6-diMe 0 CF.sub.3 H SMe853 6.6-diMe 0 CF.sub.3 H CF.sub.3854 6.6-diMe 0 OMe H Cl855 6.6-diMe 0 OMe H OMe856 6.6-diMe 1 Cl H Cl857 6.6-diMe 1 Cl H SO.sub.2 Me858 6.6-diMe 1 Cl H NO.sub.2859 6.6-diMe 1 Cl H OMe860 6.6-diMe 1 Cl H Me861 6.6-diMe 1 Cl H Br862 6.6-diMe 1 Cl H F863 6.6-diMe 1 Cl H SMe864 6.6-diMe 1 Cl H S(O)Me865 6.6-diMe 1 Cl H CF.sub.3866 6.6-diMe 1 Cl H CN867 6.6-diMe 1 Cl Cl Cl868 6.6-diMe 1 Cl Cl OMe869 6.6-diMe 1 Cl Cl SMe870 6.6-diMe 1 Cl Cl SO.sub.2 Me871 6.6-diMe 1 Cl Me Cl872 6.6-diMe 1 Cl Me SO.sub.2 Me873 6.6-diMe 1 Cl OMe Cl874 6.6-diMe 1 Cl OMe Br875 6.6-diMe 1 Cl OMe SO.sub.2 Me876 6.6-diMe 1 Cl OEt Br877 6.6-diMe 1 Br H OMe878 6.6-diMe 1 F H F879 6.6-diMe 1 I I I880 6.6-diMe 1 Me H CN881 6.6-diMe 1 Me H Me882 6.6-diMe 1 Me H OMe883 6.6-diMe 1 Me Cl Cl884 6.6-diMe 1 Me CO.sub.2 Me SO.sub.2 Me885 6.6-diMe 1 Me CH.sub.2 OMe SO.sub.2 Me886 6.6-diMe 1 Me CH(Me)OMe SO.sub.2 Me887 6.6-diMe 1 NO.sub.2 H Cl888 6.6-diMe 1 NO.sub.2 H Br889 6.6-diMe 1 NO.sub.2 H F890 6.6-diMe 1 NO.sub.2 H CN891 6.6-diMe 1 NO.sub.2 H SMe892 6.6-diMe 1 NO.sub.2 H CF.sub.3893 6.6-diMe 1 NO.sub.2 OMe Cl894 6.6-diMe 1 NO.sub.2 OMe CF.sub.3895 6.6-diMe 1 CF.sub.3 H Cl896 6.6-diMe 1 CF.sub.3 H Br897 6.6-diMe 1 CF.sub.3 H SMe898 6.6-diMe 1 CF.sub.3 H CF.sub.3899 6.6-diMe 1 OMe H Cl900 6.6-diMe 1 OMe H OMe901 6.6-diMe 2 Cl H Cl902 6.6-diMe 2 Cl H SO.sub.2 Me903 6.6-diMe 2 Cl H NO.sub.2904 6.6-diMe 2 Cl H OMe905 6.6-diMe 2 Cl H Me906 6.6-diMe 2 Cl H Br907 6.6-diMe 2 Cl H F908 6.6-diMe 2 Cl H SMe909 6.6-diMe 2 Cl H S(O)Me910 6.6-diMe 2 Cl H CF.sub.3911 6.6-diMe 2 Cl H CN912 6.6-diMe 2 Cl Cl Cl913 6.6-diMe 2 Cl Cl OMe914 6.6-diMe 2 Cl Cl SMe915 6.6-diMe 2 Cl Cl SO.sub.2 Me916 6.6-diMe 2 Cl Me Cl917 6.6-diMe 2 Cl Me SO.sub.2 Me918 6.6-diMe 2 Cl OMe Cl919 6.6-diMe 2 Cl OMe Br920 6.6-diMe 2 Cl OMe SO.sub.2 Me921 6.6-diMe 2 Cl OEt Br922 6.6-diMe 2 Br H OMe923 6.6-diMe 2 F H F924 6.6-diMe 2 I I I925 6.6-diMe 2 Me H CN926 6.6-diMe 2 Me H Me927 6.6-diMe 2 Me H OMe928 6.6-diMe 2 Me Cl Cl929 6.6-diMe 2 Me CO.sub.2 Me SO.sub.2 Me930 6.6-diMe 2 Me CH.sub.2 OMe SO.sub.2 Me931 6.6-diMe 2 Me CH(Me)OMe SO.sub.2 Me932 6.6-diMe 2 NO.sub.2 H Cl933 6.6-diMe 2 NO.sub.2 H Br934 6.6-diMe 2 NO.sub.2 H F935 6.6-diMe 2 NO.sub.2 H CN936 6.6-diMe 2 NO.sub.2 H SMe937 6.6-diMe 2 NO.sub.2 H CF.sub.3938 6.6-diMe 2 NO.sub.2 OMe Cl939 6.6-diMe 2 NO.sub.2 OMe CF.sub.3940 6.6-diMe 2 CF.sub.3 H Cl941 6.6-diMe 2 CF.sub.3 H Br942 6.6-diMe 2 CF.sub.3 H SMe943 6.6-diMe 2 CF.sub.3 H CF.sub.3944 6.6-diMe 2 OMe H Cl945 6.6-diMe 2 OMe H OMe946 4-Ph 0 Cl H Cl947 4-Ph 0 Cl H SO.sub.2 Me948 4-Ph 0 Cl H NO.sub.2949 4-Ph 0 Cl H OMe950 4-Ph 0 Cl H Me951 4-Ph 0 Cl H Br952 4-Ph 0 Cl H F953 4-Ph 0 Cl H SMe954 4-Ph 0 Cl H S(O)Me955 4-Ph 0 Cl H CF.sub.3956 4-Ph 0 Cl H CN957 4-Ph 0 Cl Cl Cl958 4-Ph 0 Cl Cl OMe959 4-Ph 0 Cl Cl SMe960 4-Ph 0 Cl Cl SO.sub.2 Me961 4-Ph 0 Cl Me Cl962 4-Ph 0 Cl Me SO.sub.2 Me963 4-Ph 0 Cl OMe Cl964 4-Ph 0 Cl OMe Br965 4-Ph 0 Cl OMe SO.sub.2 Me966 4-Ph 0 Cl OEt Br967 4-Ph 0 Br H OMe968 4-Ph 0 F H F969 4-Ph 0 I I I970 4-Ph 0 Me H CN971 4-Ph 0 Me H Me972 4-Ph 0 Me H OMe973 4-Ph 0 Me Cl Cl974 4-Ph 0 Me CO.sub.2 Me SO.sub.2 Me975 4-Ph 0 Me CH.sub.2 OMe SO.sub.2 Me976 4-Ph 0 Me CH(Me)OMe SO.sub.2 Me977 4-Ph 0 NO.sub.2 H Cl978 4-Ph 0 NO.sub.2 H Br979 4-Ph 0 NO.sub.2 H F980 4-Ph 0 NO.sub.2 H CN981 4-Ph 0 NO.sub.2 H SMe982 4-Ph 0 NO.sub.2 H CF.sub.3983 4-Ph 0 NO.sub.2 OMe Cl984 4-Ph 0 NO.sub.2 OMe CF.sub.3985 4-Ph 0 CF.sub.3 H Cl986 4-Ph 0 CF.sub.3 H Br987 4-Ph 0 CF.sub.3 H SMe988 4-Ph 0 CF.sub.3 H CF.sub.3989 4-Ph 0 OMe H Cl990 4-Ph 0 OMe H OMe991 4-Ph 1 Cl H Cl992 4-Ph 1 Cl H SO.sub.2 Me993 4-Ph 1 Cl H NO.sub.2994 4-Ph 1 Cl H OMe995 4-Ph 1 Cl H Me996 4-Ph 1 Cl H Br997 4-Ph 1 Cl H F998 4-Ph 1 Cl H SMe999 4-Ph 1 Cl H S(O)Me1000 4-Ph 1 Cl H CF.sub.31001 4-Ph 1 Cl H CN1002 4-Ph 1 Cl Cl Cl1003 4-Ph 1 Cl Cl OMe1004 4-Ph 1 Cl Cl SMe1005 4-Ph 1 Cl Cl SO.sub.2 Me1006 4-Ph 1 Cl Me Cl1007 4-Ph 1 Cl Me SO.sub.2 Me1008 4-Ph 1 Cl OMe Cl1009 4-Ph 1 Cl OMe Br1010 4-Ph 1 Cl OMe SO.sub.2 Me1011 4-Ph 1 Cl OEt Br1012 4-Ph 1 Br H OMe1013 4-Ph 1 F H F1014 4-Ph 1 I I I1015 4-Ph 1 Me H CN1016 4-Ph 1 Me H Me1017 4-Ph 1 Me H OMe1018 4-Ph 1 Me Cl Cl1019 4-Ph 1 Me CO.sub.2 Me SO.sub.2 Me1020 4-Ph 1 Me CH.sub.2 OMe SO.sub.2 Me1021 4-Ph 1 Me CH(Me)OMe SO.sub.2 Me1022 4-Ph 1 NO.sub.2 H Cl1023 4-Ph 1 NO.sub.2 H Br1024 4-Ph 1 NO.sub.2 H F1025 4-Ph 1 NO.sub.2 H CN1026 4-Ph 1 NO.sub.2 H SMe1027 4-Ph 1 NO.sub.2 H CF.sub.31028 4-Ph 1 NO.sub.2 OMe Cl1029 4-Ph 1 NO.sub.2 OMe CF.sub.31030 4-Ph 1 CF.sub.3 H Cl1031 4-Ph 1 CF.sub.3 H Br1032 4-Ph 1 CF.sub.3 H SMe1033 4-Ph 1 CF.sub.3 H CF.sub.31034 4-Ph 1 OMe H Cl1035 4-Ph 1 OMe H OMe1036 4-Ph 2 Cl H Cl1037 4-Ph 2 Cl H SO.sub.2 Me1038 4-Ph 2 Cl H NO.sub.21039 4-Ph 2 Cl H OMe1040 4-Ph 2 Cl H Me1041 4-Ph 2 Cl H Br1042 4-Ph 2 Cl H F1043 4-Ph 2 Cl H SMe1044 4-Ph 2 Cl H S(O)Me1045 4-Ph 2 Cl H CF.sub.31046 4-Ph 2 Cl H CN1047 4-Ph 2 Cl Cl Cl1048 4-Ph 2 Cl Cl OMe1049 4-Ph 2 Cl Cl SMe1050 4-Ph 2 Cl Cl SO.sub.2 Me1051 4-Ph 2 Cl Me Cl1052 4-Ph 2 Cl Me SO.sub.2 Me1053 4-Ph 2 Cl OMe Cl1054 4-Ph 2 Cl OMe Br1055 4-Ph 2 Cl OMe SO.sub.2 Me1056 4-Ph 2 Cl OEt Br1057 4-Ph 2 Br H OMe1058 4-Ph 2 F H F1059 4-Ph 2 I I I1060 4-Ph 2 Me H CN1061 4-Ph 2 Me H Me1062 4-Ph 2 Me H OMe1063 4-Ph 2 Me Cl Cl1064 4-Ph 2 Me CO.sub.2 Me SO.sub.2 Me1065 4-Ph 2 Me CH.sub.2 OMe SO.sub.2 Me1066 4-Ph 2 Me CH(Me)OMe SO.sub.2 Me1067 4-Ph 2 NO.sub.2 H Cl1068 4-Ph 2 NO.sub.2 H Br1069 4-Ph 2 NO.sub.2 H F1070 4-Ph 2 NO.sub.2 H CN1071 4-Ph 2 NO.sub.2 H SMe1072 4-Ph 2 NO.sub.2 H CF.sub.31073 4-Ph 2 NO.sub.2 OMe Cl1074 4-Ph 2 NO.sub.2 OMe CF.sub.31075 4-Ph 2 CF.sub.3 H Cl1076 4-Ph 2 CF.sub.3 H Br1077 4-Ph 2 CF.sub.3 H SMe1078 4-Ph 2 CF.sub.3 H CF.sub.31079 4-Ph 2 OMe H Cl1080 4-Ph 2 OMe H OMe1081 5-Ph 0 Cl H Cl1082 5-Ph 0 Cl H SO.sub.2 Me1083 5-Ph 0 Cl H NO.sub.21084 5-Ph 0 Cl H OMe1085 5-Ph 0 Cl H Me1086 5-Ph 0 Cl H Br1087 5-Ph 0 Cl H F1088 5-Ph 0 Cl H SMe1089 5-Ph 0 Cl H S(O)Me1090 5-Ph 0 Cl H CF.sub.31091 5-Ph 0 Cl H CN1092 5-Ph 0 Cl Cl Cl1093 5-Ph 0 Cl Cl OMe1094 5-Ph 0 Cl Cl SMe1095 5-Ph 0 Cl Cl SO.sub.2 Me1096 5-Ph 0 Cl Me Cl1097 5-Ph 0 Cl Me SO.sub.2 Me1098 5-Ph 0 Cl OMe Cl1099 5-Ph 0 Cl OMe Br1100 5-Ph 0 Cl OMe SO.sub.2 Me1101 5-Ph 0 Cl OEt Br1102 5-Ph 0 Br H OMe1103 5-Ph 0 F H F1104 5-Ph 0 I I I1105 5-Ph 0 Me H CN1106 5-Ph 0 Me H Me1107 5-Ph 0 Me H OMe1108 5-Ph 0 Me Cl Cl1109 5-Ph 0 Me CO.sub.2 Me SO.sub.2 Me1110 5-Ph 0 Me CH.sub.2 OMe SO.sub.2 Me1111 5-Ph 0 Me CH(Me)OMe SO.sub.2 Me1112 5-Ph 0 NO.sub.2 H Cl1113 5-Ph 0 NO.sub.2 H Br1114 5-Ph 0 NO.sub.2 H F1115 5-Ph 0 NO.sub.2 H CN1116 5-Ph 0 NO.sub.2 H SMe1117 5-Ph 0 NO.sub.2 H CF.sub.31118 5-Ph 0 NO.sub.2 OMe Cl1119 5-Ph 0 NO.sub.2 OMe CF.sub.31120 5-Ph 0 CF.sub.3 H Cl1121 5-Ph 0 CF.sub.3 H Br1122 5-Ph 0 CF.sub.3 H SMe1123 5-Ph 0 CF.sub.3 H CF.sub.31124 5-Ph 0 OMe H Cl1125 5-Ph 0 OMe H OMe1126 5-Ph 1 Cl H Cl1127 5-Ph 1 Cl H SO.sub.2 Me1128 5-Ph 1 Cl H NO.sub.21129 5-Ph 1 Cl H OMe1130 5-Ph 1 Cl H Me1131 5-Ph 1 Cl H Br1132 5-Ph 1 Cl H F1133 5-Ph 1 Cl H SMe1134 5-Ph 1 Cl H S(O)Me1135 5-Ph 1 Cl H CF.sub.31136 5-Ph 1 Cl H CN1137 5-Ph 1 Cl Cl Cl1138 5-Ph 1 Cl Cl OMe1139 5-Ph 1 Cl Cl SMe1140 5-Ph 1 Cl Cl SO.sub.2 Me1141 5-Ph 1 Cl Me Cl1142 5-Ph 1 Cl Me SO.sub.2 Me1143 5-Ph 1 Cl OMe Cl1144 5-Ph 1 Cl OMe Br1145 5-Ph 1 Cl OMe SO.sub.2 Me1146 5-Ph 1 Cl OEt Br1147 5-Ph 1 Br H OMe1148 5-Ph 1 F H F1149 5-Ph 1 I I I1150 5-Ph 1 Me H CN1151 5-Ph 1 Me H Me1152 5-Ph 1 Me H OMe1153 5-Ph 1 Me Cl Cl1154 5-Ph 1 Me CO.sub.2 Me SO.sub.2 Me1155 5-Ph 1 Me CH.sub.2 OMe SO.sub.2 Me1156 5-Ph 1 Me CH(Me)OMe SO.sub.2 Me1157 5-Ph 1 NO.sub.2 H Cl1158 5-Ph 1 NO.sub.2 H Br1159 5-Ph 1 NO.sub.2 H F1160 5-Ph 1 NO.sub.2 H CN1161 5-Ph 1 NO.sub.2 H SMe1162 5-Ph 1 NO.sub.2 H CF.sub.31163 5-Ph 1 NO.sub.2 OMe Cl1164 5-Ph 1 NO.sub.2 OMe CF.sub.31165 5-Ph 1 CF.sub.3 H Cl1166 5-Ph 1 CF.sub.3 H Br1167 5-Ph 1 CF.sub.3 H SMe1168 5-Ph 1 CF.sub.3 H CF.sub.31169 5-Ph 1 OMe H Cl1170 5-Ph 1 OMe H OMe1171 5-Ph 2 Cl H Cl1172 5-Ph 2 Cl H SO.sub.2 Me1173 5-Ph 2 Cl H NO.sub.21174 5-Ph 2 Cl H OMe1175 5-Ph 2 Cl H Me1176 5-Ph 2 Cl H Br1177 5-Ph 2 Cl H F1178 5-Ph 2 Cl H SMe1179 5-Ph 2 Cl H S(O)Me1180 5-Ph 2 Cl H CF.sub.31181 5-Ph 2 Cl H CN1182 5-Ph 2 Cl Cl Cl1183 5-Ph 2 Cl Cl OMe1184 5-Ph 2 Cl Cl SMe1185 5-Ph 2 Cl Cl SO.sub.2 Me1186 5-Ph 2 Cl Me Cl1187 5-Ph 2 Cl Me SO.sub.2 Me1188 5-Ph 2 Cl OMe Cl1189 5-Ph 2 Cl OMe Br1190 5-Ph 2 Cl OMe SO.sub.2 Me1191 5-Ph 2 Cl OEt Br1192 5-Ph 2 Br H OMe1193 5-Ph 2 F H F1194 5-Ph 2 I I I1195 5-Ph 2 Me H CN1196 5-Ph 2 Me H Me1197 5-Ph 2 Me H OMe1198 5-Ph 2 Me Cl Cl1199 5-Ph 2 Me CO.sub.2 Me SO.sub.2 Me1200 5-Ph 2 Me CH.sub.2 OMe SO.sub.2 Me1201 5-Ph 2 Me CH(Me)OMe SO.sub.2 Me1202 5-Ph 2 NO.sub.2 H Cl1203 5-Ph 2 NO.sub.2 H Br1204 5-Ph 2 NO.sub.2 H F1205 5-Ph 2 NO.sub.2 H CN1206 5-Ph 2 NO.sub.2 H SMe1207 5-Ph 2 NO.sub.2 H CF.sub.31208 5-Ph 2 NO.sub.2 OMe Cl1209 5-Ph 2 NO.sub.2 OMe CF.sub.31210 5-Ph 2 CF.sub.3 H Cl1211 5-Ph 2 CF.sub.3 H Br1212 5-Ph 2 CF.sub.3 H SMe1213 5-Ph 2 CF.sub.3 H CF.sub.31214 5-Ph 2 OMe H Cl1215 5-Ph 2 OMe H OMe1216 6-Ph 0 Cl H Cl1217 6-Ph 0 Cl H SO.sub.2 Me1218 6-Ph 0 Cl H NO.sub.21219 6-Ph 0 Cl H OMe1220 6-Ph 0 Cl H Me1221 6-Ph 0 Cl H Br1222 6-Ph 0 Cl H F1223 6-Ph 0 Cl H SMe1224 6-Ph 0 Cl H S(O)Me1225 6-Ph 0 Cl H CF.sub.31226 6-Ph 0 Cl H CN1227 6-Ph 0 Cl Cl Cl1228 6-Ph 0 Cl Cl OMe1229 6-Ph 0 Cl Cl SMe1230 6-Ph 0 Cl Cl SO.sub.2 Me1231 6-Ph 0 Cl Me Cl1232 6-Ph 0 Cl Me SO.sub.2 Me1233 6-Ph 0 Cl OMe Cl1234 6-Ph 0 Cl OMe Br1235 6-Ph 0 Cl OMe SO.sub.2 Me1236 6-Ph 0 Cl OEt Br1237 6-Ph 0 Br H OMe1238 6-Ph 0 F H F1239 6-Ph 0 I I I1240 6-Ph 0 Me H CN1241 6-Ph 0 Me H Me1242 6-Ph 0 Me H OMe1243 6-Ph 0 Me Cl Cl1244 6-Ph 0 Me CO.sub.2 Me SO.sub.2 Me1245 6-Ph 0 Me CH.sub.2 OMe SO.sub.2 Me1246 6-Ph 0 Me CH(Me)OMe SO.sub.2 Me1247 6-Ph 0 NO.sub.2 H Cl1248 6-Ph 0 NO.sub.2 H Br1249 6-Ph 0 NO.sub.2 H F1250 6-Ph 0 NO.sub.2 H CN1251 6-Ph 0 NO.sub.2 H SMe1252 6-Ph 0 NO.sub.2 H CF.sub.31253 6-Ph 0 NO.sub.2 OMe Cl1254 6-Ph 0 NO.sub.2 OMe CF.sub.31255 6-Ph 0 CF.sub.3 H Cl1256 6-Ph 0 CF.sub.3 H Br1257 6-Ph 0 CF.sub.3 H SMe1258 6-Ph 0 CF.sub.3 H CF.sub.31259 6-Ph 0 OMe H Cl1260 6-Ph 0 OMe H OMe1261 6-Ph 1 Cl H Cl1262 6-Ph 1 Cl H SO.sub.2 Me1263 6-Ph 1 Cl H NO.sub.21264 6-Ph 1 Cl H OMe1265 6-Ph 1 Cl H Me1266 6-Ph 1 Cl H Br1267 6-Ph 1 Cl H F1268 6-Ph 1 Cl H SMe1269 6-Ph 1 Cl H S(O)Me1270 6-Ph 1 Cl H CF.sub.31271 6-Ph 1 Cl H CN1272 6-Ph 1 Cl Cl Cl1273 6-Ph 1 Cl Cl OMe1274 6-Ph 1 Cl Cl SMe1275 6-Ph 1 Cl Cl SO.sub.2 Me1276 6-Ph 1 Cl Me Cl1277 6-Ph 1 Cl Me SO.sub.2 Me1278 6-Ph 1 Cl OMe Cl1279 6-Ph 1 Cl OMe Br1280 6-Ph 1 Cl OMe SO.sub.2 Me1281 6-Ph 1 Cl OEt Br1282 6-Ph 1 Br H OMe1283 6-Ph 1 F H F1284 6-Ph 1 I I I1285 6-Ph 1 Me H CN1286 6-Ph 1 Me H Me1287 6-Ph 1 Me H OMe1288 6-Ph 1 Me Cl Cl1289 6-Ph 1 Me CO.sub.2 Me SO.sub.2 Me1290 6-Ph 1 Me CH.sub.2 OMe SO.sub.2 Me1291 6-Ph 1 Me CH(Me)OMe SO.sub.2 Me1292 6-Ph 1 NO.sub.2 H Cl1293 6-Ph 1 NO.sub.2 H Br1294 6-Ph 1 NO.sub.2 H F1295 6-Ph 1 NO.sub.2 H CN1296 6-Ph 1 NO.sub.2 H SMe1297 6-Ph 1 NO.sub.2 H CF.sub.31298 6-Ph 1 NO.sub.2 OMe Cl1299 6-Ph 1 NO.sub.2 OMe CF.sub.31300 6-Ph 1 CF.sub.3 H Cl1301 6-Ph 1 CF.sub.3 H Br1302 6-Ph 1 CF.sub.3 H SMe1303 6-Ph 1 CF.sub.3 H CF.sub.31304 6-Ph 1 OMe H Cl1305 6-Ph 1 OMe H OMe1306 6-Ph 2 Cl H Cl1307 6-Ph 2 Cl H SO.sub.2 Me1308 6-Ph 2 Cl H NO.sub.21309 6-Ph 2 Cl H OMe1310 6-Ph 2 Cl H Me1311 6-Ph 2 Cl H Br1312 6-Ph 2 Cl H F1313 6-Ph 2 Cl H SMe1314 6-Ph 2 Cl H S(O)Me1315 6-Ph 2 Cl H CF.sub.31316 6-Ph 2 Cl H CN1317 6-Ph 2 Cl Cl Cl1318 6-Ph 2 Cl Cl OMe1319 6-Ph 2 Cl Cl SMe1320 6-Ph 2 Cl Cl SO.sub.2 Me1321 6-Ph 2 Cl Me Cl1322 6-Ph 2 Cl Me SO.sub.2 Me1323 6-Ph 2 Cl OMe Cl1324 6-Ph 2 Cl OMe Br1325 6-Ph 2 Cl OMe SO.sub.2 Me1326 6-Ph 2 Cl OEt Br1327 6-Ph 2 Br H OMe1328 6-Ph 2 F H F1329 6-Ph 2 I I I1330 6-Ph 2 Me H CN1331 6-Ph 2 Me H Me1332 6-Ph 2 Me H OMe1333 6-Ph 2 Me Cl Cl1334 6-Ph 2 Me CO.sub.2 Me SO.sub.2 Me1335 6-Ph 2 Me CH.sub.2 OMe SO.sub.2 Me1336 6-Ph 2 Me CH(Me)OMe SO.sub.2 Me1337 6-Ph 2 NO.sub.2 H Cl1338 6-Ph 2 NO.sub.2 H Br1339 6-Ph 2 NO.sub.2 H F1340 6-Ph 2 NO.sub.2 H CN1341 6-Ph 2 NO.sub.2 H SMe1342 6-Ph 2 NO.sub.2 H CF.sub.31343 6-Ph 2 NO.sub.2 OMe Cl1344 6-Ph 2 NO.sub.2 OMe CF.sub.31345 6-Ph 2 CF.sub.3 H Cl1346 6-Ph 2 CF.sub.3 H Br1347 6-Ph 2 CF.sub.3 H SMe1348 6-Ph 2 CF.sub.3 H CF.sub.31349 6-Ph 2 OMe H Cl1350 6-Ph 2 OMe H OMe1351 5-(4-ClPh) 0 Cl H Cl1352 5-(4-ClPh) 0 Cl H SO.sub.2 Me1353 5-(4-ClPh) 0 Cl H NO.sub.21354 5-(4-ClPh) 0 Cl H OMe1355 5-(4-ClPh) 0 Cl H Me1356 5-(4-ClPh) 0 Cl H Br1357 5-(4-ClPh) 0 Cl H F1358 5-(4-ClPh) 0 Cl H SMe1359 5-(4-ClPh) 0 Cl H S(O)Me1360 5-(4-ClPh) 0 Cl H CF.sub.31361 5-(4-ClPh) 0 Cl H CN1362 5-(4-ClPh) 0 Cl Cl Cl1363 5-(4-ClPh) 0 Cl Cl OMe1364 5-(4-ClPh) 0 Cl Cl SMe1365 5-(4-ClPh) 0 Cl Cl SO.sub.2 Me1366 5-(4-ClPh) 1 Cl Me Cl1367 5-(4-ClPh) 1 Cl Me SO.sub.2 Me1368 5-(4-ClPh) 1 Cl OMe Cl1369 5-(4-ClPh) 1 Cl OMe Br1370 5-(4-ClPh) 0 Cl OMe SO.sub.2 Me1371 5-(4-ClPh) 0 Cl OEt Br1372 5-(4-ClPh) 0 Br H OMe1373 5-(4-ClPh) 0 F H F1374 5-(4-ClPh) 0 I I I1375 5-(4-ClPh) 0 Me H CN1376 5-(4-ClPh) 0 Me H Me1377 5-(4-ClPh) 0 Me H OMe1378 5-(4-ClPh) 0 Me Cl Cl1379 5-(4-ClPh) 0 Me CO.sub.2 Me SO.sub.2 Me1380 5-(4-ClPh) 0 Me CH.sub.2 OMe SO.sub.2 Me1381 5-(4-ClPh) 0 Me CH(Me)OMe SO.sub.2 Me1382 5-(4-ClPh) 0 NO.sub.2 H Cl1383 5-(4-ClPh) 0 NO.sub.2 H Br1384 5-(4-ClPh) 0 NO.sub.2 H F1385 5-(4-ClPh) 0 NO.sub.2 H CN1386 5-(4-ClPh) 0 NO.sub.2 H SMe1387 5-(4-ClPh) 0 NO.sub.2 H CF.sub.31388 5-(4-ClPh) 0 NO.sub.2 OMe Cl1389 5-(4-ClPh) 0 NO.sub.2 OMe CF.sub.31390 5-(4-ClPh) 0 CF.sub.3 H Cl1391 5-(4-ClPh) 0 CF.sub.3 H Br1392 5-(4-ClPh) 0 CF.sub.3 H SMe1393 5-(4-ClPh) 0 CF.sub.3 H CF.sub.31394 5-(4-ClPh) 0 OMe H Cl1395 5-(4-ClPh) 0 OMe H OMe1396 5-(4-ClPh) 1 Cl H Cl1397 5-(4-ClPh) 1 Cl H SO.sub.2 Me1398 5-(4-ClPh) 1 Cl H NO.sub.21399 5-(4-ClPh) 1 Cl H OMe1400 5-(4-ClPh) 1 Cl H Me1401 5-(4-ClPh) 1 Cl H Br1402 5-(4-ClPh) 1 Cl H F1403 5-(4-ClPh) 1 Cl H SMe1404 5-(4-ClPh) 1 Cl H S(O)Me1405 5-(4-ClPh) 1 Cl H CF.sub.31406 5-(4-ClPh) 1 Cl H CN1407 5-(4-ClPh) 1 Cl Cl Cl1408 5-(4-ClPh) 1 Cl Cl OMe1409 5-(4-ClPh) 1 Cl Cl SMe1410 5-(4-ClPh) 1 Cl Cl SO.sub.2 Me1411 5-(4-ClPh) 1 Cl Me Cl1412 5-(4-ClPh) 1 Cl Me SO.sub.2 Me1413 5-(4-ClPh) 1 Cl OMe Cl1414 5-(4-ClPh) 1 Cl OMe Br1415 5-(4-ClPh) 1 Cl OMe SO.sub.2 Me1416 5-(4-ClPh) 1 Cl OEt Br1417 5-(4-ClPh) 1 Br H OMe1418 5-(4-ClPh) 1 F H F1419 5-(4-ClPh) 1 I I I1420 5-(4-ClPh) 1 Me H CN1421 5-(4-ClPh) 1 Me H Me1422 5-(4-ClPh) 1 Me H OMe1423 5-(4-ClPh) 1 Me Cl Cl1424 5-(4-ClPh) 1 Me CO.sub.2 Me SO.sub.2 Me1425 5-(4-ClPh) 1 Me CH.sub.2 OMe SO.sub.2 Me1426 5-(4-ClPh) 1 Me CH(Me)OMe SO.sub.2 Me1427 5-(4-ClPh) 1 NO.sub.2 H Cl1428 5-(4-ClPh) 1 NO.sub.2 H Br1429 5-(4-ClPh) 1 NO.sub.2 H F1430 5-(4-ClPh) 1 NO.sub.2 H CN1431 5-(4-ClPh) 1 NO.sub.2 H SMe1432 5-(4-ClPh) 1 NO.sub.2 H CF.sub.31433 5-(4-ClPh) 1 NO.sub.2 OMe Cl1434 5-(4-ClPh) 1 NO.sub.2 OMe CF.sub.31435 5-(4-ClPh) 1 CF.sub.3 H Cl1436 5-(4-ClPh) 1 CF.sub.3 H Br1437 5-(4-ClPh) 1 CF.sub.3 H SMe1438 5-(4-ClPh) 1 CF.sub.3 H CF.sub.31439 5-(4-ClPh) 1 OMe H Cl1440 5-(4-ClPh) 1 OMe H OMe1441 5-(4-ClPh) 2 Cl H Cl1442 5-(4-ClPh) 2 Cl H SO.sub.2 Me1443 5-(4-ClPh) 2 Cl H NO.sub.21444 5-(4-ClPh) 2 Cl H OMe1445 5-(4-ClPh) 2 Cl H Me1446 5-(4-ClPh) 2 Cl H Br1447 5-(4-ClPh) 2 Cl H F1448 5-(4-ClPh) 2 Cl H SMe1449 5-(4-ClPh) 2 Cl H S(O)Me1450 5-(4-ClPh) 2 Cl H CF.sub.31451 5-(4-ClPh) 2 Cl H CN1452 5-(4-ClPh) 2 Cl Cl Cl1453 5-(4-ClPh) 2 Cl Cl OMe1454 5-(4-ClPh) 2 Cl Cl SMe1455 5-(4-ClPh) 2 Cl Cl SO.sub.2 Me1456 5-(4-ClPh) 2 Cl Me Cl1457 5-(4-ClPh) 2 Cl Me SO.sub.2 Me1458 5-(4-ClPh) 2 Cl OMe Cl1459 5-(4-Cl Ph) 2 Cl OMe Br1460 5-(4-ClPh) 2 Cl OMe SO.sub.2 Me1461 5-(4-ClPh) 2 Cl OEt Br1462 5-(4-ClPh) 2 Br H OMe1463 5-(4-ClPh) 2 F H F1464 5-(4-ClPh) 2 I I I1465 5-(4-ClPh) 2 Me H CN1466 5-(4-ClPh) 2 Me H Me1467 5-(4-ClPh) 2 Me H OMe1468 5-(4-ClPh) 2 Me Cl Cl1469 5-(4-ClPh) 2 Me CO.sub.2 Me SO.sub.2 Me1470 5-(4-ClPh) 2 Me CH.sub.2 OMe SO.sub.2 Me1471 5-(4-ClPh) 2 Me CH(Me)OMe SO.sub.2 Me1472 5-(4-ClPh) 2 NO.sub.2 H Cl1473 5-(4-ClPh) 2 NO.sub.2 H Br1474 5-(4-ClPh) 2 NO.sub.2 H F1475 5-(4-ClPh) 2 NO.sub.2 H CN1476 5-(4-ClPh) 2 NO.sub.2 H SMe1477 5-(4-ClPh) 2 NO.sub.2 H CF.sub.31478 5-(4-ClPh) 2 NO.sub.2 OMe Cl1479 5-(4-ClPh) 2 NO.sub.2 OMe CF.sub.31480 5-(4-ClPh) 2 CF.sub.3 H Cl1481 5-(4-ClPh) 2 CF.sub.3 H Br1482 5-(4-ClPh) 2 CF.sub.3 H SMe1483 5-(4-ClPh) 2 CF.sub.3 H CF.sub.31484 5-(4-ClPh) 2 OMe H Cl1485 5-(4-ClPh) 2 OMe H OMe1486 5-(4-MePh) 0 Cl H Cl1487 5-(4-MePh) 0 Cl H SO.sub.2 Me1488 5-(4-MePh) 0 Cl H NO.sub.21489 5-(4-MePh) 0 Cl H OMe1490 5-(4-MePh) 0 Cl H Me1491 5-(4-MePh) 0 Cl H Br1492 5-(4-MePh) 0 Cl H F1493 5-(4-MePh) 0 Cl H SMe1494 5-(4-MePh) 0 Cl H S(O)Me1495 5-(4-MePh) 0 Cl H CF.sub.31496 5-(4-MePh) 0 Cl H CN1497 5-(4-MePh) 0 Cl Cl Cl1498 5-(4-MePh) 0 Cl Cl OMe1499 5-(4-MePh) 0 Cl Cl SMe1500 5-(4-MePh) 0 Cl Cl SO.sub.2 Me1501 5-(4-MePh) 0 Cl Me Cl1502 5-(4-MePh) 0 Cl Me SO.sub.2 Me1503 5-(4-MePh) 0 Cl OMe Cl1504 5-(4-MePh) 0 Cl OMe Br1505 5-(4-MePh) 0 Cl OMe SO.sub.2 Me1506 5-(4-MePh) 0 Cl OEt Br1507 5-(4-MePh) 0 Br H OMe1508 5-(4-MePh) 0 F H F1509 5-(4-MePh) 0 I I I1510 5-(4-MePh) 0 Me H CN1511 5-(4-MePh) 0 Me H Me1512 5-(4-MePh) 0 Me H OMe1513 5-(4-MePh) 0 Me Cl Cl1514 5-(4-MePh) 0 Me CO.sub.2 Me SO.sub.2 Me1515 5-(4-MePh) 0 Me CH.sub.2 OMe SO.sub.2 Me1516 5-(4-MePh) 0 Me CH(Me)OMe SO.sub.2 Me1517 5-(4-MePh) 0 NO.sub.2 H Cl1518 5-(4-MePh) 0 NO.sub.2 H Br1519 5-(4-MePh) 0 NO.sub.2 H F1520 5-(4-MePh) 0 NO.sub.2 H CN1521 5-(4-MePh) 0 NO.sub.2 H SMe1522 5-(4-MePh) 0 NO.sub.2 H CF.sub.31523 5-(4-MePh) 0 NO.sub.2 OMe Cl1524 5-(4-MePh) 0 NO.sub.2 OMe CF.sub.31525 5-(4-MePh) 0 CF.sub.3 H Cl1526 5-(4-MePh) 0 CF.sub.3 H Br1527 5-(4-MePh) 0 CF.sub.3 H SMe1528 5-(4-MePh) 0 CF.sub.3 H CF.sub.31529 5-(4-MePh) 0 OMe H Cl1530 5-(4-MePh) 0 OMe H OMe1531 5-(4-MePh) 1 Cl H Cl1532 5-(4-MePh) 1 Cl H SO.sub.2 Me1533 5-(4-MePh) 1 Cl H NO.sub.21534 5-(4-MePh) 1 Cl H OMe1535 5-(4-MePh) 1 Cl H Me1536 5-(4-MePh) 1 Cl H Br1537 5-(4-MePh) 1 Cl H F1538 5-(4-MePh) 1 Cl H SMe1539 5-(4-MePh) 1 Cl H S(O)Me1540 5-(4-MePh) 1 Cl H CF.sub.31541 5-(4-MePh) 1 Cl H CN1542 5-(4-MePh) 1 Cl Cl Cl1543 5-(4-MePh) 1 Cl Cl OMe1544 5-(4-MePh) 1 Cl Cl SMe1545 5-(4-MePh) 1 Cl Cl SO.sub.2 Me1546 5-(4-MePh) 1 Cl Me Cl1547 5-(4-MePh) 1 Cl Me SO.sub.2 Me1548 5-(4-MePh) 1 Cl OMe Cl1549 5-(4-MePh) 1 Cl OMe Br1550 5-(4-MePh) 1 Cl OMe SO.sub.2 Me1551 5-(4-MePh) 1 Cl OEt Br1552 5-(4-MePh) 1 Br H OMe1553 5-(4-MePh) 1 F H F1554 5-(4-MePh) 1 I I I1555 5-(4-MePh) 1 Me H CN1556 5-(4-MePh) 1 Me H Me1557 5-(4-MePh) 1 Me H OMe1558 5-(4-MePh) 1 Me Cl Cl1559 5-(4-MePh) 1 Me CO.sub.2 Me SO.sub.2 Me1560 5-(4-MePh) 1 Me CH.sub.2 OMe SO.sub.2 Me1561 5-(4-MePh) 1 Me CH(Me)OMe SO.sub.2 Me1562 5-(4-MePh) 1 NO.sub.2 H Cl1563 5-(4-MePh) 1 NO.sub.2 H Br1564 5-(4-MePh) 1 NO.sub.2 H F1565 5-(4-MePh) 1 NO.sub.2 H CN1566 5-(4-MePh) 1 NO.sub.2 H SMe1567 5-(4-MePh) 1 NO.sub.2 H CF.sub.31568 5-(4-MePh) 1 NO.sub.2 OMe Cl1569 5-(4-MePh) 1 NO.sub.2 OMe CF.sub.31570 5-(4-MePh) 1 CF.sub.3 H Cl1571 5-(4-MePh) 1 CF.sub.3 H Br1572 5-(4-MePh) 1 CF.sub.3 H SMe1573 5-(4-MePh) 1 CF.sub.3 H CF.sub.31574 5-(4-MePh) 1 OMe H Cl1575 5-(4-MePh) 1 OMe H OMe1576 5-(4-MePh) 2 Cl H Cl1577 5-(4-MePh) 2 Cl H SO.sub.2 Me1578 5-(4-MePh) 2 Cl H NO.sub.21579 5-(4-MePh) 2 Cl H OMe1580 5-(4-MePh) 2 Cl H Me1581 5-(4-MePh) 2 Cl H Br1582 5-(4-MePh) 2 Cl H F1583 5-(4-MePh) 2 Cl H SMe1584 5-(4-MePh) 2 Cl H S(O)Me1585 5-(4-MePh) 2 Cl H CF.sub.31586 5-(4-MePh) 2 Cl H CN1587 5-(4-MePh) 2 Cl Cl Cl1588 5-(4-MePh) 2 Cl Cl OMe1589 5-(4-MePh) 2 Cl Cl SMe1590 5-(4-MePh) 2 Cl Cl SO.sub.2 Me1591 5-(4-MePh) 2 Cl Me Cl1592 5-(4-MePh) 2 Cl Me SO.sub.2 Me1593 5-(4-MePh) 2 Cl OMe Cl1594 5-(4-MePh) 2 Cl OMe Br1595 5-(4-MePh) 2 Cl OMe SO.sub.2 Me1596 5-(4-MePh) 2 Cl OEt Br1597 5-(4-MePh) 2 Br H OMe1598 5-(4-MePh) 2 F H F1599 5-(4-MePh) 2 I I I1600 5-(4-MePh) 2 Me H CN1601 5-(4-MePh) 2 Me H Me1602 5-(4-MePh) 2 Me H OMe1603 5-(4-MePh) 2 Me Cl Cl1604 5-(4-MePh) 2 Me CO.sub.2 Me SO.sub.2 Me1605 5-(4-MePh) 2 Me CH.sub.2 OMe SO.sub.2 Me1606 5-(4-MePh) 2 Me CH(Me)OMe SO.sub.2 Me1607 5-(4-MePh) 2 NO.sub.2 H Cl1608 5-(4-MePh) 2 NO.sub.2 H Br1609 5-(4-MePh) 2 NO.sub.2 H F1610 5-(4-MePh) 2 NO.sub.2 H CN1611 5-(4-MePh) 2 NO.sub.2 H SMe1612 5-(4-MePh) 2 NO.sub.2 H CF.sub.31613 5-(4-MePh) 2 NO.sub.2 OMe Cl1614 5-(4-MePh) 2 NO.sub.2 OMe CF.sub.31615 5-(4-MePh) 2 CF.sub.3 H Cl1616 5-(4-MePh) 2 CF.sub.3 H Br1617 5-(4-MePh) 2 CF.sub.3 H SMe1618 5-(4-MePh) 2 CF.sub.3 H CF.sub.31619 5-(4-MePh) 2 OMe H Cl1620 5-(4-MePh) 2 OMe H OMe__________________________________________________________________________
TABLE 2__________________________________________________________________________ ##STR17##Compound No. of Characteristicthe present invention (R).sub.m L X Y Z (Physical property)__________________________________________________________________________1621 -- 0 Cl H Cl1622 -- 0 Cl H SO.sub.2 Me1623 -- 0 Cl H NO.sub.21624 -- 0 Cl H OMe1625 -- 0 Cl H Me1626 -- 0 Cl H Br1627 -- 0 Cl H F1628 -- 0 Cl H SMe1629 -- 0 Cl H S(O)Me1630 -- 0 Cl H CF.sub.31631 -- 0 Cl H CN1632 -- 0 Cl Cl Cl1633 -- 0 Cl Cl OMe1634 -- 0 Cl Cl SMe1635 -- 0 Cl Cl SO.sub.2 Me1636 -- 0 Cl Me Cl1637 -- 0 Cl Me SO.sub.2 Me1638 -- 0 Cl OMe Cl1639 -- 0 Cl OMe Br1640 -- 0 Cl OMe SO.sub.2 Me1641 -- 0 Cl OEt Br1642 -- 0 Br H OMe1643 -- 0 F H F1644 -- 0 I I I1645 -- 0 Me H CN1626 -- 0 Me H Me1627 -- 0 Me H OMe1628 -- 0 Me Cl Cl1629 -- 0 Me CO.sub.2 Me SO.sub.2 Me1630 -- 0 Me CH.sub.2 OMe SO.sub.2 Me1631 -- 0 Me CH(Me)OMe SO.sub.2 Me1632 -- 0 NO.sub.2 H Cl1633 -- 0 NO.sub.2 H Br1634 -- 0 NO.sub.2 H F1635 -- 0 NO.sub.2 H CN1636 -- 0 NO.sub.2 H SMe1637 -- 0 NO.sub.2 H CF.sub.31638 -- 0 NO.sub.2 OMe Cl1639 -- 0 NO.sub. 2 OMe CF.sub.31640 -- 0 CF.sub.3 H Cl1641 -- 0 CF.sub.3 H Br1642 -- 0 CF.sub.3 H SMe1643 -- 0 CF.sub.3 H CF.sub.31644 -- 0 OMe H Cl1645 -- 0 OMe H OMe1646 -- 1 Cl H Cl1647 -- 1 Cl H SO.sub.2 Me1648 -- 1 Cl H NO.sub.21649 -- 1 Cl H OMe1650 -- 1 Cl H Me1651 -- 1 Cl H Br1652 -- 1 Cl H F1653 -- 1 Cl H SMe1654 -- 1 Cl H S(O)Me1655 -- 1 Cl H CF.sub.31656 -- 1 Cl H CN1657 -- 1 Cl Cl Cl1658 -- 1 Cl Cl OMe1659 -- 1 Cl Cl SMe1660 -- 1 Cl Cl SO.sub.2 Me1661 -- 1 Cl Me Cl1662 -- 1 Cl Me SO.sub.2 Me1663 -- 1 Cl OMe Cl1664 -- 1 Cl OMe Br1665 -- 1 Cl OMe SO.sub.2 Me1666 -- 1 Cl Oet Br1667 -- 1 Br H OMe1668 -- 1 F H F1669 -- 1 I I I1670 -- 1 Me H CN1671 -- 1 Me H Me1672 -- 1 Me H OMe1673 -- 1 Me Cl Cl1674 -- 1 Me CO.sub.2 Me SO.sub.2 Me1675 -- 1 Me CH.sub.2 OMe SO.sub.2 Me1676 -- 1 Me CH(Me)OMe SO.sub.2 Me1677 -- 1 NO.sub.2 H Cl1678 -- 1 NO.sub.2 H Br1679 -- 1 NO.sub.2 H F1680 -- 1 NO.sub.2 H CN1681 -- 1 NO.sub.2 H SMe1682 -- 1 NO.sub.2 H CF.sub.31683 -- 1 NO.sub.2 OMe Cl1684 -- 1 NO.sub.2 OMe CF.sub.31685 -- 1 CF.sub.3 H Cl1686 -- 1 CF.sub.3 H Br1687 -- 1 CF.sub.3 H SMe1688 -- 1 CF.sub.3 H CF.sub.31689 -- 1 OMe H Cl1690 -- 1 OMe H OMe1691 -- 2 Cl H Cl1692 -- 2 Cl H SO.sub.2 Me1693 -- 2 Cl H NO.sub.21694 -- 2 Cl H OMe1695 -- 2 Cl H Me1696 -- 2 Cl H Br1697 -- 2 Cl H F1698 -- 2 Cl H SMe1699 -- 2 Cl H S(O)Me1700 -- 2 Cl H CF.sub.31701 -- 2 Cl H CN1702 -- 2 Cl Cl Cl1703 -- 2 Cl Cl OMe1704 -- 2 Cl Cl SMe1705 -- 2 Cl Cl SO.sub.2 Me1706 -- 2 Cl Me Cl1707 -- 2 Cl Me SO.sub.2 Me1708 -- 2 Cl OMe Cl1709 -- 2 Cl OMe Br1710 -- 2 Cl OMe SO.sub.2 Me1711 -- 2 Cl OEt Br1712 -- 2 Br H OMe1713 -- 2 F H F1714 -- 2 I I I1715 -- 2 Me H CN1716 -- 2 Me H Me1717 -- 2 Me H OMe1718 -- 2 Me Cl Cl1719 -- 2 Me CO.sub.2 Me SO.sub.2 Me1720 -- 2 Me CH.sub.2 OMe SO.sub.2 Me1721 -- 2 Me CH(Me)OMe SO.sub.2 Me1722 -- 2 NO.sub.2 H Cl1723 -- 2 NO.sub.2 H Br1724 -- 2 NO.sub.2 H F1725 -- 2 NO.sub.2 H CN1726 -- 2 NO.sub.2 H SMe1727 -- 2 NO.sub.2 H CF.sub.31728 -- 2 NO.sub.2 OMe Cl1729 -- 2 NO.sub.2 OMe CF.sub.31730 -- 2 CF.sub.3 H Cl1731 -- 2 CF.sub.3 H Br1732 -- 2 CF.sub.3 H SMe1733 -- 2 CF.sub.3 H CF.sub.31734 -- 2 OMe H Cl1735 -- 2 OMe H OMe1736 4-Me 0 Cl H Cl Dark green crystal m.p. 55.about.58.degree. C.1737 4-Me 0 Cl H SO.sub.2 Me1738 4-Me 0 Cl H NO.sub.21739 4-Me 0 Cl H OMe1740 4-Me 0 Cl H Me1741 4-Me 0 Cl H Br1742 4-Me 0 Cl H F1743 4-Me 0 Cl H SMe1744 4-Me 0 Cl H S(O)Me1745 4-Me 0 Cl H CF.sub.31746 4-Me 0 Cl H CN1747 4-Me 0 Cl Cl Cl1748 4-Me 0 Cl Cl OMe1749 4-Me 0 Cl Cl SMe1750 4-Me 0 Cl Cl SO.sub.2 Me1751 4-Me 0 Cl Me Cl1752 4-Me 0 Cl Me SO.sub.2 Me1753 4-Me 0 Cl OMe Cl1754 4-Me 0 Cl OMe Br1755 4-Me 0 Cl OMe SO.sub.2 Me1756 4-Me 0 Cl OEt Br1757 4-Me 0 Br H OMe1758 4-Me 0 F H F1759 4-Me 0 I I I1760 4-Me 0 Me H CN1761 4-Me 0 Me H Me1762 4-Me 0 Me H OMe1763 4-Me 0 Me Cl Cl1764 4-Me 0 Me CO.sub.2 Me SO.sub.2 Me1765 4-Me 0 Me CH.sub.2 OMe SO.sub.2 Me1766 4-Me 0 Me CH(Me)OMe SO.sub.2 Me1767 4-Me 0 NO.sub.2 H Cl1768 4-Me 0 NO.sub.2 H Br1769 4-Me 0 NO.sub.2 H F1770 4-Me 0 NO.sub.2 H CN1771 4-Me 0 NO.sub.2 H SMe1772 4-Me 0 NO.sub.2 H CF.sub.31773 4-Me 0 NO.sub.2 OMe Cl1774 4-Me 0 NO.sub.2 OMe CF.sub.31775 4-Me 0 CF.sub.3 H Cl1776 4-Me 0 CF.sub.3 H Br1777 4-Me 0 CF.sub.3 H SMe1778 4-Me 0 CF.sub.3 H CF.sub.31779 4-Me 0 OMe H Cl1780 4-Me 0 OMe H OMe1781 4-Me 1 Cl H Cl1782 4-Me 1 Cl H SO.sub.2 Me1783 4-Me 1 Cl H NO.sub.21784 4-Me 1 Cl H OMe1785 4-Me 1 Cl H Me1786 4-Me 1 Cl H Br1787 4-Me 1 Cl H F1788 4-Me 1 Cl H SMe1789 4-Me 1 Cl H S(O)Me1790 4-Me 1 Cl H CF.sub.31791 4-Me 1 Cl H CN1792 4-Me 1 Cl Cl Cl1793 4-Me 1 Cl Cl OMe1794 4-Me 1 Cl Cl SMe1795 4-Me 1 Cl Cl SO.sub.2 Me1796 4-Me 1 Cl Me Cl1797 4-Me 1 Cl Me SO.sub.2 Me1798 4-Me 1 Cl OMe Cl1799 4-Me 1 Cl OMe Br1800 4-Me 1 Cl OMe SO.sub.2 Me1801 4-Me 1 Cl OEt Br1802 4-Me 1 Br H OMe1803 4-Me 1 F H F1804 4-Me 1 I I I1805 4-Me 1 Me H CN1806 4-Me 1 Me H Me1807 4-Me 1 Me H OMe1808 4-Me 1 Me Cl Cl1809 4-Me 1 Me CO.sub.2 Me SO.sub.2 Me1810 4-Me 1 Me CH.sub.2 OMe SO.sub.2 Me1811 4-Me 1 Me CH(Me)OMe SO.sub.2 Me1812 4-Me 1 NO.sub.2 H Cl1813 4-Me 1 NO.sub.2 H Br1814 4-Me 1 NO.sub.2 H F1815 4-Me 1 NO.sub.2 H CN1816 4-Me 1 NO.sub.2 H SMe1817 4-Me 1 NO.sub.2 H CF.sub.31818 4-Me 1 NO.sub.2 OMe Cl1819 4-Me 1 NO.sub.2 OMe CF.sub.31820 4-Me 1 CF.sub.3 H Cl1821 4-Me 1 CF.sub.3 H Br1822 4-Me 1 CF.sub.3 H SMe1823 4-Me 1 CF.sub.3 H CF.sub.31824 4-Me 1 OMe H Cl1825 4-Me 1 OMe H OMe1826 4-Me 2 Cl H Cl1827 4-Me 2 Cl H SO.sub.2 Me1828 4-Me 2 Cl H NO.sub.21829 4-Me 2 Cl H OMe1830 4-Me 2 Cl H Me1831 4-Me 2 Cl H Br1832 4-Me 2 Cl H F1833 4-Me 2 Cl H SMe1834 4-Me 2 Cl H S(O)Me1835 4-Me 2 Cl H CF.sub.31836 4-Me 2 Cl H CN1837 4-Me 2 Cl Cl Cl1838 4-Me 2 Cl Cl OMe1839 4-Me 2 Cl Cl SMe1840 4-Me 2 Cl Cl SO.sub.2 Me1841 4-Me 2 Cl Me Cl1842 4-Me 2 Cl Me SO.sub.2 Me1843 4-Me 2 Cl OMe Cl1844 4-Me 2 Cl OMe Br1845 4-Me 2 Cl OMe SO.sub.2 Me1846 4-Me 2 Cl Oet Br1847 4-Me 2 Br H OMe1848 4-Me 2 F H F1849 4-Me 2 I I I1850 4-Me 2 Me H CN1851 4-Me 2 Me H Me1852 4-Me 2 Me H OMe1853 4-Me 2 Me Cl Cl1854 4-Me 2 Me CO.sub.2 Me SO.sub.2 Me1855 4-Me 2 Me CH.sub.2 OMe SO.sub.2 Me1856 4-Me 2 Me CH(Me)OMe SO.sub.2 Me1857 4-Me 2 NO.sub.2 H Cl1858 4-Me 2 NO.sub.2 H Br1859 4-Me 2 NO.sub.2 H F1860 4-Me 2 NO.sub.2 H CN1861 4-Me 2 NO.sub.2 H SMe1862 4-Me 2 NO.sub.2 H CF.sub.31863 4-Me 2 NO.sub.2 OMe Cl1864 4-Me 2 NO.sub.2 OMe CF.sub.31865 4-Me 2 CF.sub.3 H Cl1866 4-Me 2 CF.sub.3 H Br1867 4-Me 2 CF.sub.3 H Br1868 4-Me 2 CF.sub.3 H CF.sub.31869 4-Me 2 OMe H Cl1870 4-Me 2 OMe H OMe1871 5-Me 0 Cl H Cl1872 5-Me 0 Cl H SO.sub.2 Me1873 5-Me 0 Cl H NO.sub.21874 5-Me 0 Cl H OMe1875 5-Me 0 Cl H Me1876 5-Me 0 Cl H Br1877 5-Me 0 Cl H F1878 5-Me 0 Cl H SMe1879 5-Me 0 Cl H S(O)Me1880 5-Me 0 Cl H CF.sub.31881 5-Me 0 Cl H CN1882 5-Me 0 Cl Cl Cl1883 5-Me 0 Cl Cl OMe1884 5-Me 0 Cl Cl SMe1885 5-Me 0 Cl Cl SO.sub.2 Me1886 5-Me 0 Cl Me Cl1887 5-Me 0 Cl Me SO.sub.2 Me1888 5-Me 0 Cl OMe Cl1889 5-Me 0 Cl OMe Br1890 5-Me 0 Cl OMe SO.sub.2 Me1891 5-Me 0 Cl OEt Br1892 5-Me 0 Br H OMe1893 5-Me 0 F H F1894 5-Me 0 I I I1895 5-Me 0 Me H CN1896 5-Me 0 Me H Me1897 5-Me 0 Me H OMe1898 5-Me 0 Me Cl Cl1899 5-Me 0 Me CO.sub.2 Me SO.sub.2 Me1900 5-Me 0 Me CH.sub.2 OMe SO.sub.2 Me1901 5-Me 0 Me CH(Me)OMe SO.sub.2 Me1902 5-Me 0 NO.sub.2 H Cl1903 5-Me 0 NO.sub.2 H Br1904 5-Me 0 NO.sub.2 H F1905 5-Me 0 NO.sub.2 H CN1906 5-Me 0 NO.sub.2 H SMe1907 5-Me 0 NO.sub.2 H CF.sub.31908 5-Me 0 NO.sub.2 OMe Cl1909 5-Me 0 NO.sub.2 OMe CF.sub.31910 5-Me 0 CF.sub.3 H Cl1911 5-Me 0 CF.sub.3 H Br1912 5-Me 0 CF.sub.3 H SMe1913 5-Me 0 CF.sub.3 H CF.sub.31914 5-Me 0 OMe H Cl1915 5-Me 0 OMe H OMe1916 5-Me 1 Cl H Cl1917 5-Me 1 Cl H SO.sub.2 Me1918 5-Me 1 Cl H NO.sub.21919 5-Me 1 Cl H OMe1920 5-Me 1 Cl H Me1921 5-Me 1 Cl H Br1922 5-Me 1 Cl H F1923 5-Me 1 Cl H SMe1924 5-Me 1 Cl H S(O)Me1925 5-Me 1 Cl H CF.sub.31926 5-Me 1 Cl H CN1927 5-Me 1 Cl Cl Cl1928 5-Me 1 Cl Cl OMe1929 5-Me 1 Cl Cl SMe1930 5-Me 1 Cl Cl SO.sub.2 Me1931 5-Me 1 Cl Me Cl1932 5-Me 1 Cl Me SO.sub.2 Me1933 5-Me 1 Cl OMe Cl1934 5-Me 1 Cl OMe Br1935 5-Me 1 Cl OMe SO.sub.2 Me1936 5-Me 1 Cl OEt Br1937 5-Me 1 Br H OMe1938 5-Me 1 F H F1939 5-Me 1 I I I1940 5-Me 1 Me H CN1941 5-Me 1 Me H Me1942 5-Me 1 Me H OMe1943 5-Me 1 Me Cl Cl1944 5-Me 1 Me CO.sub.2 Me SO.sub.2 Me1945 5-Me 1 Me CH.sub.2 OMe SO.sub.2 Me1946 5-Me 1 Me CH(Me)OMe SO.sub.2 Me1947 5-Me 1 NO.sub.2 H Cl1948 5-Me 1 NO.sub.2 H Br1949 5-Me 1 NO.sub.2 H F1950 5-Me 1 NO.sub.2 H CN1951 5-Me 1 NO.sub.2 H SMe1952 5-Me 1 NO.sub.2 H CF.sub.31953 5-Me 1 NO.sub.2 OMe Cl1954 5-Me 1 NO.sub.2 OMe CF.sub.31955 5-Me 1 CF.sub.3 H Cl1956 5-Me 1 CF.sub.3 H Br1957 5-Me 1 CF.sub.3 H SMe1958 5-Me 1 CF.sub.3 H CF.sub.31959 5-Me 1 OMe H Cl1960 5-Me 1 OMe H OMe1961 5-Me 2 Cl H Cl1962 5-Me 2 Cl H SO.sub.2 Me1963 5-Me 2 Cl H NO.sub.21964 5-Me 2 Cl H OMe1965 5-Me 2 Cl H Me1966 5-Me 2 Cl H Br1967 5-Me 2 Cl H F1968 5-Me 2 Cl H SMe1969 5-Me 2 Cl H S(O)Me1970 5-Me 2 Cl H CF.sub.31971 5-Me 2 Cl H CN1972 5-Me 2 Cl Cl Cl1973 5-Me 2 Cl Cl OMe1974 5-Me 2 Cl Cl SMe1975 5-Me 2 Cl Cl SO.sub.2 Me1976 5-Me 2 Cl Me Cl1977 5-Me 2 Cl Me SO.sub.2 Me1978 5-Me 2 Cl OMe Cl1979 5-Me 2 Cl OMe Br1980 5-Me 2 Cl OMe SO.sub.2 Me1981 5-Me 2 Cl OEt Br1982 5-Me 2 Br H OMe1983 5-Me 2 F H F1984 5-Me 2 I I I1985 5-Me 2 Me H CN1986 5-Me 2 Me H Me1987 5-Me 2 Me H OMe1988 5-Me 2 Me Cl Cl1989 5-Me 2 Me CO.sub.2 Me SO.sub.2 Me1990 5-Me 2 Me CH.sub.2 OMe SO.sub.2 Me1991 5-Me 2 Me CH(Me)OMe SO.sub.2 Me1992 5-Me 2 NO.sub.2 H Cl1993 5-Me 2 NO.sub.2 H Br1994 5-Me 2 NO.sub.2 H F1995 5-Me 2 NO.sub.2 H CN1996 5-Me 2 NO.sub.2 H SMe1997 5-Me 2 NO.sub.2 H CF.sub.31998 5-Me 2 NO.sub.2 OMe Cl1999 5-Me 2 NO.sub.2 OMe CF.sub.32000 5-Me 2 CF.sub.3 H Cl2001 5-Me 2 CF.sub.3 H Br2002 5-Me 2 CF.sub.3 H SMe2003 5-Me 2 CF.sub.3 H CF.sub.32004 5-Me 2 OMe H Cl2005 5-Me 2 OMe H OMe2006 4.4-diMe 0 Cl H Cl2007 4.4-diMe 0 Cl H SO.sub.2 Me2008 4.4-diMe 0 Cl H NO.sub.22009 4.4-diMe 0 Cl H OMe2010 4.4-diMe 0 Cl H Me2011 4.4-diMe 0 Cl H Br2012 2.4-diMe 0 Cl H F2013 4.4-diMe 0 Cl H SMe2014 4.4-diMe 0 Cl H S(O)Me2015 4.4-diMe 0 Cl H CF.sub.32016 4.4-diMe 0 Cl H CN2017 4.4-diMe 0 Cl Cl Cl2018 4.4-diMe 0 Cl Cl OMe2019 4.4-diMe 0 Cl Cl SMe2020 4.4-diMe 0 Cl Cl SO.sub.2 Me2021 4.4-diMe 0 Cl Me Cl2022 4.4-diMe 0 Cl Me SO.sub.2 Me2023 4.4-diMe 0 Cl OMe Cl2024 4.4-diMe 0 Cl OMe Br2025 4.4-diMe 0 Cl OMe SO.sub.2 Me2026 4.4-diMe 0 Cl OEt Br2027 4.4-diMe 0 Br H OMe2028 4.4-diMe 0 F H F2029 4.4-diMe 0 I I I2030 4.4-diMe 0 Me H CN2031 4.4-diMe 0 Me H Me2032 4.4-diMe 0 Me H OMe2033 4.4-diMe 0 Me Cl Cl2034 4.4-diMe 0 Me CO.sub.2 Me SO.sub.2 Me2035 4.4-diMe 0 Me CH.sub.2 OMe SO.sub.2 Me2036 4.4-diMe 0 Me CH(Me)OMe SO.sub.2 Me2037 4.4-diMe 0 NO.sub.2 H Cl2038 4.4-diMe 0 NO.sub.2 H Br2039 4.4-diMe 0 NO.sub.2 H F2040 4.4-diMe 0 NO.sub.2 H CN2041 4.4-diMe 0 NO.sub.2 H SMe2042 4.4-diMe 0 NO.sub.2 H CF.sub.32043 4.4-diMe 0 NO.sub.2 OMe Cl2044 4.4-diMe 0 NO.sub.2 OMe CF.sub.32045 4.4-diMe 0 CF.sub.3 H Cl2046 4.4-diMe 0 CF.sub.3 H Br2047 4.4-diMe 0 CF.sub.3 H SMe2048 4.4-diMe 0 CF.sub.3 H CF.sub.32049 4.4-diMe 0 OMe H Cl2050 4.4-diMe 0 OMe H OMe2051 4.4-diMe 1 Cl H Cl2052 4.4-diMe 1 Cl H SO.sub.2 Me2053 4.4-diMe 1 Cl H NO.sub.22054 4.4-diMe 1 Cl H OMe2055 4.4-diMe 1 Cl H Me2056 4.4-diMe 1 Cl H Br2057 4.4-diMe 1 Cl H F2058 4.4-diMe 1 Cl H SMe2059 4.4-diMe 1 Cl H S(O)Me2060 4.4-diMe 1 Cl H CF.sub.32061 4.4-diMe 1 Cl H CN2062 4.4-diMe 1 Cl Cl Cl2063 4.4-diMe 1 Cl Cl OMe2064 4.4-diMe 1 Cl Cl SMe2065 4.4-diMe 1 Cl Cl SO.sub.2 Me2066 4.4-diMe 1 Cl Me Cl2067 4.4-diMe 1 Cl Me SO.sub.2 Me2068 4.4-diMe 1 Cl OMe Cl2069 4.4-diMe 1 Cl OMe Br2070 4.4-diMe 1 Cl OMe SO.sub.2 Me2071 4.4-diMe 1 Cl OEt Br2072 4.4-diMe 1 Br H OMe2073 4.4-diMe 1 F H F2074 4.4-diMe 1 I I I2075 4.4-diMe 1 Me H CN2076 4.4-diMe 1 Me H Me2077 4.4-diMe 1 Me H OMe2078 4.4-diMe 1 Me Cl Cl2079 4.4-diMe 1 Me CO.sub.2 Me SO.sub.2 Me2080 4.4-diMe 1 Me CH.sub.2 OMe SO.sub.2 Me2081 4.4-diMe 1 Me CH(Me)OMe SO.sub.2 Me2082 4.4-diMe 1 NO.sub.2 H Cl2083 4.4-diMe 1 NO.sub.2 H Br2084 4.4-diMe 1 NO.sub.2 H F2085 4.4-diMe 1 NO.sub.2 H CN2086 4.4-diMe 1 NO.sub.2 H SMe2087 4.4-diMe 1 NO.sub.2 H CF.sub.32088 4.4-diMe 1 NO.sub.2 OMe Cl2089 4.4-diMe 1 NO.sub.2 OMe CF.sub.32090 4.4-diMe 1 CF.sub.3 H Cl2091 4.4-diMe 1 CF.sub.3 H Br2092 4.4-diMe 1 CF.sub.3 H SMe2093 4.4-diMe 1 CF.sub.3 H CF.sub.32094 4.4-diMe 1 OMe H Cl2095 4.4-diMe 1 OMe H OMe2096 4.4-diMe 2 Cl H Cl2097 4.4-diMe 2 Cl H SO.sub.2 Me2098 4.4-diMe 2 Cl H NO.sub.22099 4.4-diMe 2 Cl H OMe2100 4.4-diMe 2 Cl H Me2101 4.4-diMe 2 Cl H Br2102 4.4-diMe 2 Cl H F2103 4.4-diMe 2 Cl H SMe2104 4.4-diMe 2 Cl H S(O)Me2105 4.4-diMe 2 Cl H CF.sub.32106 4.4-diMe 2 Cl H CN2107 4.4-diMe 2 Cl Cl Cl2108 4.4-diMe 2 Cl Cl OMe2109 4.4-diMe 2 Cl Cl SMe2110 4.4-diMe 2 Cl Cl SO.sub.2 Me2111 4.4-diMe 2 Cl Me Cl2112 4.4-diMe 2 Cl Me SO.sub.2 Me2113 4.4-diMe 2 Cl OMe Cl2114 4.4-diMe 2 Cl OMe Br2115 4.4-diMe 2 Cl OMe SO.sub.2 Me2116 4.4-diMe 2 Cl OEt Br2117 4.4-diMe 2 Br H OMe2118 4.4-diMe 2 F H F2119 4.4-diMe 2 I I I2120 4.4-diMe 2 Me H CN2121 4.4-diMe 2 Me H Me2122 4.4-diMe 2 Me H OMe2123 4.4-diMe 2 Me Cl Cl2124 4.4-diMe 2 Me CO.sub.2 Me SO.sub.2 Me2125 4.4-diMe 2 Me CH.sub.2 OMe SO.sub.2 Me2126 4.4-diMe 2 Me CH(Me)OMe SO.sub.2 Me2127 4.4-diMe 2 NO.sub.2 H Cl2128 4.4-diMe 2 NO.sub.2 H Br2129 4.4-diMe 2 NO.sub.2 H F2130 4.4-diMe 2 NO.sub.2 H CN2131 4.4-diMe 2 NO.sub.2 H SMe2132 4.4-diMe 2 NO.sub.2 H CF.sub.32133 4.4-diMe 2 NO.sub.2 OMe Cl2134 4.4-diMe 2 NO.sub.2 OMe CF.sub.32135 4.4-diMe 2 CF.sub.3 H Cl2136 4.4-diMe 2 CF.sub.3 H Br2137 4.4-diMe 2 CF.sub.3 H SMe2138 4.4-diMe 2 CF.sub.3 H CF.sub.32139 4.4-diMe 2 OMe H Cl2140 4.4-diMe 2 OMe H OMe2141 5.5-diMe 0 Cl H Cl2142 5.5-diMe 0 Cl H SO.sub.2 Me2143 5.5-diMe 0 Cl H NO.sub.22144 5.5-diMe 0 Cl H OMe2145 5.5-diMe 0 Cl H Me2146 5.5-diMe 0 Cl H Br2147 5.5-diMe 0 Cl H F2148 5.5-diMe 0 Cl H SMe2149 5.5-diMe 0 Cl H S(O)Me2150 5.5-diMe 0 Cl H CF.sub.32151 5.5-diMe 0 Cl H CN2152 5.5-diMe 0 Cl Cl Cl2153 5.5-diMe 0 Cl Cl OMe2154 5.5-diMe 0 Cl Cl SMe2155 5.5-diMe 0 Cl Cl SO.sub.2 Me2156 5.5-diMe 0 Cl Me Cl2157 5.5-diMe 0 Cl Me SO.sub.2 Me2158 5.5-diMe 0 Cl OMe Cl2159 5.5-diMe 0 Cl OMe Br2160 5.5-diMe 0 Cl OMe SO.sub.2 Me2161 5.5-diMe 0 Cl OEt Br2162 5.5-diMe 0 Br H OMe2163 5.5-diMe 0 F H F2164 5.5-diMe 0 I I I2165 5.5-diMe 0 Me H CN2166 5.5-diMe 0 Me H Me2167 5.5-diMe 0 Me H OMe2168 5.5-diMe 0 Me Cl Cl2169 5.5-diMe 0 Me CO.sub.2 Me SO.sub.2 Me2170 5.5-diMe 0 Me CH.sub.2 OMe SO.sub.2 Me2171 5.5-diMe 0 Me CH(Me)OMe SO.sub.2 Me2172 5.5-diMe 0 NO.sub.2 H Cl2173 5.5-diMe 0 NO.sub.2 H Br2174 5.5-diMe 0 NO.sub.2 H F2175 5.5-diMe 0 NO.sub.2 H CN2176 5.5-diMe 0 NO.sub.2 H SMe2177 5.5-diMe 0 NO.sub.2 H CF.sub.32178 5.5-diMe 0 NO.sub.2 OMe Cl2179 5.5-diMe 0 NO.sub.2 OMe CF.sub.32180 5.5-diMe 0 CF.sub.3 H Cl2181 5.5-diMe 0 CF.sub.3 H Br2182 5.5-diMe 0 CF.sub.3 H SMe2183 5.5-diMe 0 CF.sub.3 H CF.sub.32184 5.5-diMe 0 OMe H Cl2185 5.5-diMe 0 OMe H OMe2186 5.5-diMe 0 Cl H Cl2187 5.5-diMe 0 Cl H SO.sub.2 Me2188 5.5-diMe 0 Cl H NO.sub.22189 5.5-diMe 0 Cl H OMe2190 5.5-diMe 0 Cl H Me2191 5.5-diMe 1 Cl H Br2192 5.5-diMe 1 Cl H F2193 5.5-diMe 1 Cl H SMe2194 5.5-diMe 1 Cl H S(O)Me2195 5.5-diMe 1 Cl H CF.sub.32196 5.5-diMe 1 Cl H CN2197 5.5-diMe 1 Cl Cl Cl2198 5.5-diMe 1 Cl Cl OMe2199 5.5-diMe 1 Cl Cl SMe2200 5.5-diMe 1 Cl Cl SO.sub.2 Me2201 5.5-diMe 1 Cl Me Cl2202 5.5-diMe 1 Cl Me SO.sub.2 Me2203 5.5-diMe 1 Cl OMe Cl2204 5.5-diMe 1 Cl OMe Br2205 5.5-diMe 1 Cl OMe SO.sub.2 Me2206 5.5-diMe 1 Cl OEt Br2207 5.5-diMe 1 Br H OMe2208 5.5-diMe 1 F H F2209 5.5-diMe 1 I I I2210 5.5-diMe 1 Me H CN2211 5.5-diMe 1 Me H Me2212 5.5-diMe 1 Me H OMe2213 5.5-diMe 1 Me Cl Cl2214 5.5-diMe 1 Me CO.sub.2 Me SO.sub.2 Me2215 5.5-diMe 1 Me CH.sub.2 OMe SO.sub.2 Me2216 5.5-diMe 1 Me CH(Me)OMe SO.sub.2 Me2217 5.5-diMe 1 NO.sub.2 H Cl2218 5.5-diMe 1 NO.sub.2 H Br2219 5.5-diMe 1 NO.sub.2 H F2220 5.5-diMe 1 NO.sub.2 H CN2221 5.5-diMe 1 NO.sub.2 H SMe2222 5.5-diMe 1 NO.sub.2 H CF.sub.32223 5.5-diMe 1 NO.sub.2 OMe Cl2224 5.5-diMe 1 NO.sub.2 OMe CF.sub.32225 5.5-diMe 1 CF.sub.3 H Cl2226 5.5-diMe 1 CF.sub.3 H Br2227 5.5-diMe 1 CF.sub.3 H SMe2228 5.5-diMe 1 CF.sub.3 H CF.sub.32229 5.5-diMe 1 OMe H Cl2230 5.5-diMe 1 OMe H OMe2231 5.5-diMe 2 Cl H Cl2232 5.5-diMe 2 Cl H SO.sub.2 Me2233 5.5-diMe 2 Cl H NO.sub.22234 5.5-diMe 2 Cl H OMe2235 5.5-diMe 2 Cl H Me2236 5.5-diMe 2 Cl H Br2237 5.5-diMe 2 Cl H F2238 5.5-diMe 2 Cl H SMe2239 5.5-diMe 2 Cl H S(O)Me2240 5.5-diMe 2 Cl H CF.sub.32241 5.5-diMe 2 Cl H CN2242 5.5-diMe 2 Cl Cl Cl2243 5.5-diMe 2 Cl Cl OMe2244 5.5-diMe 2 Cl Cl SMe2245 5.5-diMe 2 Cl Cl SO.sub.2 Me2246 5.5-diMe 2 Cl Me Cl2247 5.5-diMe 2 Cl Me SO.sub.2 Me2248 5.5-diMe 2 Cl OMe Cl2249 5.5-diMe 2 Cl OMe Br2250 5.5-diMe 2 Cl OMe SO.sub.2 Me2251 5.5-diMe 2 Cl OEt Br2252 5.5-diMe 2 Br H OMe2253 5.5-diMe 2 F H F2254 5.5-diMe 2 I I I2255 5.5-diMe 2 Me H CN2256 5.5-diMe 2 Me H Me2257 5.5-diMe 2 Me H OMe2258 5.5-diMe 2 Me Cl Cl2259 5.5-diMe 2 Me CO.sub.2 Me SO.sub.2 Me2260 5.5-diMe 2 Me CH.sub.2 OMe SO.sub.2 Me2261 5.5-diMe 2 Me CH(Me)OMe SO.sub.2 Me2262 5.5-diMe 2 NO.sub.2 H Cl2263 5.5-diMe 2 NO.sub.2 H Br2264 5.5-diMe 2 NO.sub.2 H F2265 5.5-diMe 2 NO.sub.2 H CN2266 5.5-diMe 2 NO.sub.2 H SMe2267 5.5-diMe 2 NO.sub.2 H CF.sub.32268 5.5-diMe 2 NO.sub.2 OMe Cl2269 5.5-diMe 2 NO.sub.2 OMe CF.sub.32270 5.5-diMe 2 CF.sub.3 H Cl2271 5.5-diMe 2 CF.sub.3 H Br2272 5.5-diMe 2 CF.sub.3 H SMe2273 5.5-diMe 2 CF.sub.3 H CF.sub.32274 5.5-diMe 2 OMe H Cl2275 5.5-diMe 2 OMe H OMe2276 4.5-diMe 0 Cl H Cl2277 4.5-diMe 0 Cl H SO.sub.2 Me2278 4.5-diMe 0 Cl H NO.sub.22279 4.5-diMe 0 Cl H OMe2280 4.5-diMe 0 Cl H Me2281 4.5-diMe 0 Cl H Br2282 4.5-diMe 0 Cl H F2283 4.5-diMe 0 Cl H SMe2284 4.5-diMe 0 Cl H S(O)Me2285 4.5-diMe 0 Cl H CF.sub.32286 4.5-diMe 0 Cl H CN2287 4.5-diMe 0 Cl Cl Cl2288 4.5-diMe 0 Cl Cl OMe2289 4.5-diMe 0 Cl Cl SMe2290 4.5-diMe 0 Cl Cl SO.sub.2 Me2291 4.5-diMe 0 Cl Me Cl2292 4.5-diMe 0 Cl Me SO.sub.2 Me2293 4.5-diMe 0 Cl OMe Cl2294 4.5-diMe 0 Cl OMe Br2295 4.5-diMe 0 Cl OMe SO.sub.2 Me2296 4.5-diMe 0 Cl OEt Br2297 4.5-diMe 0 Br H OMe2298 4.5-diMe 0 F H F2299 4.5-diMe 0 I I I2300 4.5-diMe 0 Me H CN2301 4.5-diMe 0 Me H Me2302 4.5-diMe 0 Me H OMe2303 4.5-diMe 0 Me Cl Cl2304 4.5-diMe 0 Me CO.sub.2 Me SO.sub.2 Me2305 4.5-diMe 0 Me CH.sub.2 OMe SO.sub.2 Me2306 4.5-diMe 0 Me CH(Me)OMe SO.sub.2 Me2307 4.5-diMe 0 NO.sub.2 H Cl2308 4.5-diMe 0 NO.sub.2 H Br2309 4.5-diMe 0 NO.sub.2 H F2310 4.5-diMe 0 NO.sub.2 H CN2311 4.5-diMe 0 NO.sub.2 H SMe2312 4.5-diMe 0 NO.sub.2 H CF.sub.32313 4.5-diMe 0 NO.sub.2 OMe Cl2314 4.5-diMe 0 NO.sub.2 OMe CF.sub.32315 4.5-diMe 0 CF.sub.3 H Cl2316 4.5-diMe 0 CF.sub.3 H Br2317 4.5-diMe 0 CF.sub.3 H SMe2318 4.5-diMe 0 CF.sub.3 H CF.sub.32319 4.5-diMe 0 OMe H Cl2320 4.5-diMe 0 OMe H OMe2321 4.5-diMe 1 Cl H Cl2322 4.5-diMe 1 Cl H SO.sub.2 Me2323 4.5-diMe 1 Cl H NO.sub.22324 4.5-diMe 1 Cl H OMe2325 4.5-diMe 1 Cl H Me2326 4.5-diMe 1 Cl H Br2327 4.5-diMe 1 Cl H F2328 4.5-diMe 1 Cl H SMe2329 4.5-diMe 1 Cl H S(O)Me2330 4.5-diMe 1 Cl H CF.sub.32331 4.5-diMe 1 Cl H CN2332 4.5-diMe 1 Cl Cl Cl2333 4.5-diMe 1 Cl Cl OMe2334 4.5-diMe 1 Cl Cl SMe2335 4.5-diMe 1 Cl Cl SO.sub.2 Me2336 4.5-diMe 1 Cl Me Cl2337 4.5-diMe 1 Cl Me SO.sub.2 Me2338 4.5-diMe 1 Cl OMe Cl2339 4.5-diMe 1 Cl OMe Br2340 4.5-diMe 1 Cl OMe SO.sub.2 Me2341 4.5-diMe 1 Cl OEt Br2342 4.5-diMe 1 Br H OMe2343 4.5-diMe 1 F H F2344 4.5-diMe 1 I I I2345 4.5-diMe 1 Me H CN2346 4.5-diMe 1 Me H Me2347 4.5-diMe 1 Me H OMe2348 4.5-diMe 1 Me Cl Cl2349 4.5-diMe 1 Me CO.sub.2 Me SO.sub.2 Me2350 4.5-diMe 1 Me CH.sub.2 OMe SO.sub.2 Me2351 4.5-diMe 1 Me CH(Me)OMe SO.sub.2 Me2352 4.5-diMe 1 NO.sub.2 H Cl2353 4.5-diMe 1 NO.sub.2 H Br2354 4.5-diMe 1 NO.sub.2 H F2355 4.5-diMe 1 NO.sub.2 H CN2356 4.5-diMe 1 NO.sub.2 H SMe2357 4.5-diMe 1 NO.sub.2 H CF.sub.32358 4.5-diMe 1 NO.sub.2 OMe Cl2359 4.5-diMe 1 NO.sub.2 OMe CF.sub.32360 4.5-diMe 1 CF.sub.3 H Cl2361 4.5-diMe 1 CF.sub.3 H Br2362 4.5-diMe 1 CF.sub.3 H SMe2363 4.5-diMe 1 CF.sub.3 H CF.sub.32364 4.5-diMe 1 OMe H Cl2365 4.5-diMe 1 OMe H OMe2366 4.5-diMe 2 Cl H Cl2367 4.5-diMe 2 Cl H SO.sub.2 Me2368 4.5-diMe 2 Cl H NO.sub.22369 4.5-diMe 2 Cl H OMe2370 4.5-diMe 2 Cl H Me2371 4.5-diMe 2 Cl H Br2372 4.5-diMe 2 Cl H F2373 4.5-diMe 2 Cl H SMe2374 4.5-diMe 2 Cl H S(O)Me2375 4.5-diMe 2 Cl H CF.sub.32376 4.5-diMe 2 Cl H CN2377 4.5-diMe 2 Cl Cl Cl2378 4.5-diMe 2 Cl Cl OMe2379 4.5-diMe 2 Cl Cl SMe2380 4.5-diMe 2 Cl Cl SO.sub.2 Me2381 4.5-diMe 2 Cl Me Cl2382 4.5-diMe 2 Cl Me SO.sub.2 Me2383 4.5-diMe 2 Cl OMe Cl2384 4.5-diMe 2 Cl OMe Br2385 4.5-diMe 2 Cl OMe SO.sub.2 Me2386 4.5-diMe 2 Cl OEt Br2387 4.5-diMe 2 Br H OMe2388 4.5-diMe 2 F H F2389 4.5-diMe 2 I I I2390 4.5-diMe 2 Me H CN2391 4.5-diMe 2 Me H Me2392 4.5-diMe 2 Me H OMe2393 4.5-diMe 2 Me Cl Cl2394 4.5-diMe 2 Me CO.sub.2 Me SO.sub.2 Me2395 4.5-diMe 2 Me CH.sub.2 OMe SO.sub.2 Me2396 4.5-diMe 2 Me CH(Me)OMe SO.sub.2 Me2397 4.5-diMe 2 NO.sub.2 H Cl2398 4.5-diMe 2 NO.sub.2 H Br2399 4.5-diMe 2 NO.sub.2 H F2400 4.5-diMe 2 NO.sub.2 H CN2401 4.5-diMe 2 NO.sub.2 H SMe2402 4.5-diMe 2 NO.sub.2 H CF.sub.32403 4.5-diMe 2 NO.sub.2 OMe Cl2404 4.5-diMe 2 NO.sub.2 OMe CF.sub.32405 4.5-diMe 2 CF.sub.3 H Cl2406 4.5-diMe 2 CF.sub.3 H Br2407 4.5-diMe 2 CF.sub.3 H SMe2408 4.5-diMe 2 CF.sub.3 H CF.sub.32409 4.5-diMe 2 OMe H Cl2410 4.5-diMe 2 OMe H OMe2411 4-Ph 0 Cl H Cl2412 4-Ph 0 Cl H SO.sub.2 Me2413 4-Ph 0 Cl H NO.sub.22414 4-Ph 0 Cl H OMe2415 4-Ph 0 Cl H Me2416 4-Ph 0 Cl H Br2417 4-Ph 0 Cl H F2418 4-Ph 0 Cl H SMe2419 4-Ph 0 Cl H S(O)Me2420 4-Ph 0 Cl H CF.sub.32421 4-Ph 0 Cl H CN2422 4-Ph 0 Cl Cl Cl2423 4-Ph 0 Cl Cl OMe2424 4-Ph 0 Cl Cl SMe2425 4-Ph 0 Cl Cl SO.sub.2 Me2426 4-Ph 0 Cl Me Cl2427 4-Ph 0 Cl Me SO.sub.2 Me2428 4-Ph 0 Cl OMe Cl2429 4-Ph 0 Cl OMe Br2430 4-Ph 0 Cl OMe SO.sub.2 Me2431 4-Ph 0 Cl OEt Br2432 4-Ph 0 Br H OMe2433 4-Ph 0 F H F2434 4-Ph 0 I I I2435 4-Ph 0 Me H CN2436 4-Ph 0 Me H Me2437 4-Ph 0 Me H OMe2438 4-Ph 0 Me Cl Cl2439 4-Ph 0 Me CO.sub.2 Me SO.sub.2 Me2440 4-Ph 0 Me CH.sub.2 OMe SO.sub.2 Me2441 4-Ph 0 Me CH(Me)OMe SO.sub.2 Me2442 4-Ph 0 NO.sub.2 H Cl2443 4-Ph 0 NO.sub.2 H Br2444 4-Ph 0 NO.sub.2 H F2445 4-Ph 0 NO.sub.2 H CN2446 4-Ph 0 NO.sub.2 H SMe2447 4-Ph 0 NO.sub.2 H CF.sub.32448 4-Ph 0 NO.sub.2 OMe Cl2449 4-Ph 0 NO.sub. 2 OMe CF.sub.32450 4-Ph 0 CF.sub.3 H Cl2451 4-Ph 0 CF.sub.3 H Br2452 4-Ph 0 CF.sub.3 H SMe2453 4-Ph 0 CF.sub.3 H CF.sub.32454 4-Ph 0 OMe H Cl2455 4-Ph 0 OMe H OMe2456 4-Ph 1 Cl H Cl2457 4-Ph 1 Cl H SO.sub.2 Me2458 4-Ph 1 Cl H NO.sub.22459 4-Ph 1 Cl H OMe2460 4-Ph 1 Cl H Me2461 4-Ph 1 Cl H Br2462 4-Ph 1 Cl H F2463 4-Ph 1 Cl H SMe2464 4-Ph 1 Cl H S(O)Me2465 4-Ph 1 Cl H CF.sub.32466 4-Ph 1 Cl H CN2467 4-Ph 1 Cl Cl Cl2468 4-Ph 1 Cl Cl OMe2469 4-Ph 1 Cl Cl SMe2470 4-Ph 1 Cl Cl SO.sub.2 Me2471 4-Ph 1 Cl Me Cl2472 4-Ph 1 Cl Me SO.sub.2 Me2473 4-Ph 1 Cl OMe Cl2474 4-Ph 1 Cl OMe Br2475 4-Ph 1 Cl OMe SO.sub.2 Me2476 4-Ph 1 Cl OEt Br2477 4-Ph 1 Br H OMe2478 4-Ph 1 F H F2479 4-Ph 1 I I I2480 4-Ph 1 Me H CN2481 4-Ph 1 Me H Me2482 4-Ph 1 Me H OMe2483 4-Ph 1 Me Cl Cl2484 4-Ph 1 Me CO.sub.2 Me SO.sub.2 Me2485 4-Ph 1 Me CH.sub.2 OMe SO.sub.2 Me2486 4-Ph 1 Me CH(Me)OMe SO.sub.2 Me2487 4-Ph 1 NO.sub.2 H Cl2488 4-Ph 1 NO.sub.2 H Br2489 4-Ph 1 NO.sub.2 H F2490 4-Ph 1 NO.sub.2 H CN2491 4-Ph 1 NO.sub.2 H SMe2492 4-Ph 1 NO.sub.2 H CF.sub.32493 4-Ph 1 NO.sub.2 OMe Cl2494 4-Ph 1 NO.sub.2 OMe CF.sub.32495 4-Ph 1 CF.sub.3 H Cl2496 4-Ph 1 CF.sub.3 H Br2497 4-Ph 1 CF.sub.3 H SMe2498 4-Ph 1 CF.sub.3 H CF.sub.32499 4-Ph 1 OMe H Cl2500 4-Ph 1 OMe H OMe2501 4-Ph 2 Cl H Cl2502 4-Ph 2 Cl H SO.sub.2 Me2503 4-Ph 2 Cl H NO.sub.22504 4-Ph 2 Cl H OMe2505 4-Ph 2 Cl H Me2506 4-Ph 2 Cl H Br2507 4-Ph 2 Cl H F2508 4-Ph 2 Cl H SMe2509 4-Ph 2 Cl H S(O)Me2510 4-Ph 2 Cl H CF.sub.32511 4-Ph 2 Cl H CN2512 4-Ph 2 Cl Cl Cl2513 4-Ph 2 Cl Cl OMe2514 4-Ph 2 Cl Cl SMe2515 4-Ph 2 Cl Cl SO.sub.2 Me2516 4-Ph 2 Cl Me Cl2517 4-Ph 2 Cl Me SO.sub.2 Me2518 4-Ph 2 Cl OMe Cl2519 4-Ph 2 Cl OMe Br2520 4-Ph 2 Cl OMe SO.sub.2 Me2521 4-Ph 2 Cl OEt Br2522 4-Ph 2 Br H OMe2523 4-Ph 2 F H F2524 4-Ph 2 I I I2525 4-Ph 2 Me H CN2526 4-Ph 2 Me H Me2527 4-Ph 2 Me H OMe2528 4-Ph 2 Me Cl Cl2529 4-Ph 2 Me CO.sub.2 Me SO.sub.2 Me2530 4-Ph 2 Me CH.sub.2 OMe SO.sub.2 Me2531 4-Ph 2 Me CH(Me)OMe SO.sub.2 Me2532 4-Ph 2 NO.sub.2 H Cl2533 4-Ph 2 NO.sub.2 H Br2534 4-Ph 2 NO.sub.2 H F2535 4-Ph 2 NO.sub.2 H CN2536 4-Ph 2 NO.sub.2 H SMe2537 4-Ph 2 NO.sub.2 H CF.sub.32538 4-Ph 2 NO.sub.2 OMe Cl2539 4-Ph 2 NO.sub.2 OMe CF.sub.32540 4-Ph 2 CF.sub.3 H Cl2541 4-Ph 2 CF.sub.3 H Br2542 4-Ph 2 CF.sub.3 H SMe2543 4-Ph 2 CF.sub.3 H CF.sub.32544 4-Ph 2 OMe H Cl2545 4-Ph 2 OMe H OMe2546 5-Ph 0 Cl H Cl2547 5-Ph 0 Cl H SO.sub.2 Me2548 5-Ph 0 Cl H NO.sub.22549 5-Ph 0 Cl H OMe2550 5-Ph 0 Cl H Me2551 5-Ph 0 Cl H Br2552 5-Ph 0 Cl H F2553 5-Ph 0 Cl H SMe2554 5-Ph 0 Cl H S(O)Me2555 5-Ph 0 Cl H CF.sub.32556 5-Ph 0 Cl H CN2557 5-Ph 0 Cl Cl Cl2558 5-Ph 0 Cl Cl OMe2559 5-Ph 0 Cl Cl SMe2560 5-Ph 0 Cl Cl SO.sub.2 Me2561 5-Ph 0 Cl Me Cl2562 5-Ph 0 Cl Me SO.sub.2 Me2563 5-Ph 0 Cl OMe Cl2564 5-Ph 0 Cl OMe Br2565 5-Ph 0 Cl OMe SO.sub.2 Me2566 5-Ph 0 Cl OEt Br2567 5-Ph 0 Br H OMe2568 5-Ph 0 F H F2569 5-Ph 0 I I I2570 5-Ph 0 Me H CN2571 5-Ph 0 Me H Me2572 5-Ph 0 Me H OMe2573 5-Ph 0 Me Cl Cl2574 5-Ph 0 Me CO.sub.2 Me SO.sub.2 Me2575 5-Ph 0 Me CH.sub.2 OMe SO.sub.2 Me2576 5-Ph 0 Me CH(Me)OMe SO.sub.2 Me2577 5-Ph 0 NO.sub.2 H Cl2578 5-Ph 0 NO.sub.2 H Br2579 5-Ph 0 NO.sub.2 H F2580 5-Ph 0 NO.sub.2 H CN2581 5-Ph 0 NO.sub.2 H SMe2582 5-Ph 0 NO.sub.2 H CF.sub.32583 5-Ph 0 NO.sub.2 OMe Cl2584 5-Ph 0 NO.sub.2 OMe CF.sub.32585 5-Ph 0 CF.sub.3 H Cl2586 5-Ph 0 CF.sub.3 H Br2587 5-Ph 0 CF.sub.3 H SMe2588 5-Ph 0 CF.sub.3 H CF.sub.32589 5-Ph 0 OMe H Cl2590 5-Ph 0 OMe H OMe2591 5-Ph 1 Cl H Cl2592 5-Ph 1 Cl H SO.sub.2 Me2593 5-Ph 1 Cl H NO.sub.22594 5-Ph 1 Cl H OMe2595 5-Ph 1 Cl H Me2596 5-Ph 1 Cl H Br2597 5-Ph 1 Cl H F2598 5-Ph 1 Cl H SMe2599 5-Ph 1 Cl H S(O)Me2600 5-Ph 1 Cl H CF.sub.32601 5-Ph 1 Cl H CN2602 5-Ph 1 Cl Cl Cl2603 5-Ph 1 Cl Cl OMe2604 5-Ph 1 Cl Cl SMe2605 5-Ph 1 Cl Cl SO.sub.2 Me2606 5-Ph 1 Cl Me Cl2607 5-Ph 1 Cl Me SO.sub.2 Me2608 5-Ph 1 Cl OMe Cl2609 5-Ph 1 Cl OMe Br2610 5-Ph 1 Cl OMe SO.sub.2 Me2611 5-Ph 1 Cl OEt Br2612 5-Ph 1 Br H OMe2613 5-Ph 1 F H F2614 5-Ph 1 I I I2615 5-Ph 1 Me H CN2616 5-Ph 1 Me H Me2617 5-Ph 1 Me H OMe2618 5-Ph 1 Me Cl Cl2619 5-Ph 1 Me CO.sub.2 Me SO.sub.2 Me2620 5-Ph 1 Me CH.sub.2 OMe SO.sub.2 Me2621 5-Ph 1 Me CH(Me)OMe SO.sub.2 Me2622 5-Ph 1 NO.sub.2 H Cl2623 5-Ph 1 NO.sub.2 H Br2624 5-Ph 1 NO.sub.2 H F2625 5-Ph 1 NO.sub.2 H CN2626 5-Ph 1 NO.sub. 2 H SMe2627 5-Ph 1 NO.sub.2 H CF.sub.32628 5-Ph 1 NO.sub.2 OMe Cl2629 5-Ph 1 NO.sub.2 OMe CF.sub.32630 5-Ph 1 CF.sub.3 H Cl2631 5-Ph 1 CF.sub.3 H Br2632 5-Ph 1 CF.sub.3 H SMe2633 5-Ph 1 CF.sub.3 H CF.sub.32634 5-Ph 1 OMe H Cl2635 5-Ph 1 OMe H OMe2636 5-Ph 2 Cl H Cl2637 5-Ph 2 Cl H SO.sub.2 Me2638 5-Ph 2 Cl H NO.sub.22639 5-Ph 2 Cl H OMe2640 5-Ph 2 Cl H Me2641 5-Ph 2 Cl H Br2642 5-Ph 2 Cl H F2643 5-Ph 2 Cl H SMe2644 5-Ph 2 Cl H S(O)Me2645 5-Ph 2 Cl H CF.sub.32646 5-Ph 2 Cl H CN2647 5-Ph 2 Cl Cl Cl2648 5-Ph 2 Cl Cl OMe2649 5-Ph 2 Cl Cl SMe2650 5-Ph 2 Cl Cl SO.sub.2 Me2651 5-Ph 2 Cl Me Cl2652 5-Ph 2 Cl Me SO.sub.2 Me2653 5-Ph 2 Cl OMe Cl2654 5-Ph 2 Cl OMe Br2655 5-Ph 2 Cl OMe SO.sub.2 Me2656 5-Ph 2 Cl OEt Br2657 5-Ph 2 Br H OMe2658 5-Ph 2 F H F2659 5-Ph 2 I I I2660 5-Ph 2 Me H CN2661 5-Ph 2 Me H Me2662 5-Ph 2 Me H OMe2663 5-Ph 2 Me Cl Cl2664 5-Ph 2 Me CO.sub.2 Me SO.sub.2 Me2665 5-Ph 2 Me CH.sub.2 OMe SO.sub.2 Me2666 5-Ph 2 Me CH(Me)OMe SO.sub.2 Me2667 5-Ph 2 NO.sub.2 H Cl2668 5-Ph 2 NO.sub.2 H Br2669 5-Ph 2 NO.sub.2 H F2670 5-Ph 2 NO.sub.2 H CN2671 5-Ph 2 NO.sub.2 H SMe2672 5-Ph 2 NO.sub.2 H CF.sub.32673 5-Ph 2 NO.sub.2 OMe Cl2674 5-Ph 2 NO.sub.2 OMe CF.sub.32675 5-Ph 2 CF.sub.3 H Cl2676 5-Ph 2 CF.sub.3 H Br2677 5-Ph 2 CF.sub.3 H SMe2678 5-Ph 2 CF.sub.3 H CF.sub.32679 5-Ph 2 OMe H Cl2680 5-Ph 2 OMe H OMe__________________________________________________________________________
TABLE 3______________________________________Com-poundNo. ofthe Dosepresent (kg/invention ha) EC DI CY SO GA RO ZE TR______________________________________ 1 0.5 5 5 5 5 5 5 0 0 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 0 7 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 016 0.5 5 5 5 5 5 5 0 0 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 017 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 029 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 030 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 032 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 037 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 01736 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 0______________________________________
TABLE 4______________________________________Com-poundNo. ofthe Dosepresent (kg/invention ha) EC DI CY SO GA RO ZE TR______________________________________ 1 0.5 5 5 5 5 5 5 0 0 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 0 7 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 016 0.5 5 5 5 5 5 5 0 0 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 017 0.5 5 5 5 5 5 5 0 0 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 030 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 032 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 037 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 01736 1.0 5 5 5 5 5 5 0 0 2.0 5 5 5 5 5 5 0 0______________________________________

Substituted benzoyl derivatives and herbicidal compositions

Information

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Agents

CPC

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Abstract

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US Referenced Citations (1)

Non-Patent Literature Citations (2)

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Entry
Rossy, "Aromatization . . . ", J. Org. Chem, 45(4) 617-20, 1980.
Konosu, "Synthesis . . . " Chem. Pharm. Bull, 38 (5) 1258-1265, 1990.