Herbicidal sulfonamides

Abstract

Certain sulfonylurea compounds such as 2-[[[4-methoxy-6-(methylselenylmethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester and 2-[[[4-methoxy-6-(phenylthiomethyl)pyrimidin-2-yl]-aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester provide herbicidal activity.

Description

BACKGROUND OF THE INVENTION

The present invention relates to a class of sulfonylurea compounds, agriculturally suitable compositions containing them and their method-of-use as pre-emergent and/or post-emergent herbicides or plant growth regulants.

Sulfonylurea compounds exhibiting herbicidal activity are disclosed in U.S. Pat. Nos. 4,127,405 and 4,169,719. Herbicidal benzenesulfonylurea compounds containing an ortho-carboxy ester group are disclosed in U.S. Pat. No. 4,383,113.

European Application No. 84,224, published July 27, 1983 discloses herbicidal sulfonylureas such as ##STR1##

European Application No. 9419 published Apr. 2, 1980 discloses herbicidal sulfonylureas such as ##STR2## where ##STR3## R.sub.4 is Cl, Br, F, NO.sub.2, CH.sub.3, OCH.sub.3, CF.sub.3 or S(O).sub.n R.sub.3 ;

X is CH.sub.3 or OCH.sub.3 ; and Y is CH.sub.2 F, CH.sub.2 Cl, CH.sub.2 Br, C.sub.2 -C.sub.4 alkenyl, etc.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as pre-emergent and/or post-emergent herbicides or plant growth regulants. ##STR4## wherein R is H or CH.sub.3 ; ##STR5## R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, F, Cl, Br, NO.sub.2, CF.sub.3, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.18, S(O).sub.n R.sub.19, WCF.sub.3, WCHF.sub.2, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.6 H.sub.5, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, ##STR6## R.sub.2 is H, F, Cl, Br, CF.sub.3, CH.sub.3, OCH.sub.3 or SCH.sub.3 ; R.sub.3 is H, CH.sub.3, OCH.sub.3, F, Cl, Br, SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3 or S(O).sub.n CH.sub.3 ;

R.sub.4 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.19 ; R.sub.5 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.19 ; R.sub.6 is Cl, NO.sub.2, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3, SO.sub.2 CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; R.sub.7 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; R.sub.8 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; R.sub.9 is H or CH.sub.3 ; R.sub.10 is H or CH.sub.3 ; R.sub.11 is H or CH.sub.3 ; R.sub.12 is C.sub.1 -C.sub.3 alkyl; R.sub.13 is H or C.sub.1 -C.sub.3 alkyl; R.sub.14 is H or CH.sub.3 ; R.sub.15 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.dbd.CH.sub.2 ; R.sub.16 is C.sub.1 -C.sub.2 alkyl; R.sub.17 is C.sub.1 -C.sub.2 alkyl; R.sub.18 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ; R.sub.19 is C.sub.1 -C.sub.3 alkyl or CH.sub.2 CH.dbd.CH.sub.2 ; m is 0 or 1; n is 0 or 2; Q.sub.1 is O, S or SO.sub.2 ; Q.sub.2 is O or S; and W is O, S or SO.sub.2 ; A is ##STR7## X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, F, Cl, Br, CF.sub.3 or OCHF.sub.2 ; T is H, SeCH.sub.3, SeC.sub.6 H.sub.5, SCH.sub.3 or ##STR8## Y is SeCH.sub.3, SeC.sub.6 H.sub.5, ##STR9## OSi(CH.sub.3).sub.3, CH.sub.2 OH or CH.sub.2 OSi(CH.sub.3).sub.3 ; Z is CH or N; X.sub.1 is CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; E is F, Cl or Br; G is CH(OCH.sub.3).sub.2, CH(OC.sub.2 H.sub.5).sub.2, ##STR10## or C.sub.6 H.sub.5 ; R.sub.20 is H, CH.sub.3, CF.sub.3, OCH.sub.3, F, Cl, Br or NO.sub.2 ; p is 0, 1 or 2; and q is 0, 1 or 2; provided that (1) when X is F, Cl or Br, then Z is CH; (2) when m is 1, then R.sub.9 is H; (3) the sum of p and q is less than or equal to 2; (4) when A is A-2 and L is L-1, then R.sub.1 is C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.18, WCF.sub.3, WCHF.sub.2, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, C.sub.6 H.sub.5, ##STR11## (5) when A is A-4, then L is L-1, L-2, L-3, L-4, L-5, L-6, L-7, L-8 or L-9; (6) when A is A-4 and L is L-1, then R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, F, Cl, Br, NO.sub.2, CF.sub.3, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.18, S(O).sub.n C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, C.sub.6 H.sub.5, ##STR12## (7) when A is A-5 and L is L-1, then R.sub.1 is C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkoxy, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, C.sub.6 H.sub.5, ##STR13## (8) when A is A-5, L is L-1 and R.sub.1 is SO.sub.2 NR.sub.16 R.sub.17 or SO.sub.2 N(OCH.sub.3)CH.sub.3, then E is F or Br; (9) when A is A-5 and L is L-4, L-5 or L-6, then R.sub.5 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.19 ; (10) when A is A-5 and L is L-10, L-11, L-12, L-13, L-14, L-15, L-16 or L-17, then E is Cl or Br; (11) when A is A-5, then L is other than L-8, L-11 or L-17; and (12) R.sub.13 and R.sub.14 are not simultaneously H; and their agriculturally suitable salts.

Preferred for reasons of their higher herbicidal acivity, greater plant growth regulant activity and/or more favorable ease of synthesis are:

(1) Compounds of Formula I where R is H and A is A-1; (2) Compounds of Preferred 1 where R.sub.2 is H, R.sub.20 is H, X is CH.sub.3 or OCH.sub.3, T is H, p is 0 and q is 0; (3) Compounds of Preferred 2 where L is L-1, L-5, L-8, L-10, L-11, L-15 or L-17; (4) Compounds of Preferred 3 where L is L-1 and R.sub.1 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, NO.sub.2, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, OSO.sub.2 CH.sub.3 or WCHF.sub.2.

Specifically preferred for reasons of their highest herbicidal activity, greatest plant growth regulant activity and/or most favorable ease of synthesis are:

2-[[[4-methoxy-6-(phenoxymethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 178.degree.-180.degree. C.; 2-[[[bis(4,6-trifluoromethyl]pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 153.degree.-161.degree. C.; 2-[[[4-methoxy-6-(methylselenylmethyl)pyrimidin-2-yl]aminocarbonyl[aminosulfonyl]benzoic acid, methyl ester, m.p. 126.degree.-130.degree. C.; and 2-[[[4-methoxy-6-(phenylthiomethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 149.degree.-152.degree. C.

DETAILED DESCRIPTION OF THE INVENTION

Synthesis

The compounds of Formula I can be prepared by reacting an appropriate sulfonyl isocyanate II with the appropriately substituted aminoheterocycle III, as shown in Equation 1. R, A and L are as previously defined. ##STR14##

The reaction is best performed in an inert solvent such as methylene chloride or toluene at 25.degree. to 100.degree. C., for 1 to 24 hours. Isolation of the product can be achieved by concentrating the solution and trituration with an appropriate solvent such as butyl chloride.

Alternatively, compounds of Formula I may be prepared by reacting the sulfonamides of Formula IV with the carbamates of Formula V (R'=CH.sub.3) in the presence of an excess of trimethylaluminum, as shown in Equation 2, where L, R and A are as previously defined, provided R.sub.1 is other than CO.sub.2 R.sub.15. ##STR15##

The reactions are best performed in an inert solvent such as methylene chloride at the reflux point of the solution (40.degree. C.) for 10 to 24 hours. Isolation of the product is best achieved by exposing the reaction mixture to acetic acid, separation of the layers and concentrating the organic layer to a solid.

Alternatively, compounds of Formula I can be prepared by exposing a phenyl carbamate V (R'=Ph) to the sulfonamide IV in an appropriate solvent such as dioxane at 25.degree. to 100.degree. C. in the presence of a strong base such as 1,8-diazabicyclo[5.4.0]undec-7-ene; acid workup affords the desired product. See EPO Publication No. 44,807 for details. The required carbamates can be prepared from the corresponding amines III and dimethyl or diphenyl carbonate or methyl or phenyl chloroformate and a base such as sodium hydride.

The sulfonyl isocyantes II used in the preparation of I are known in the art and can be prepared by known methods. For example, isocyanates can be prepared by exposing an appropriate benzene or heterocyclic sulfonamide to phosgene in the presence of an alkyl isocyanate and an amine catalyst such as 1,4-diazabicyclo[2.2.2]octane at the reflux point of the solvent. See H. Ulrich and A. A. Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Forest Ed.

The sulfonamides IV used in the preparation of I are also known in the art and can be prepared by known methods. For example, exposure of a sulfonyl chloride to ammonium hydroxide results in the formation of the corresponding sulfonamides, e.g., Crossley et al., J. Am. Chem. Soc., 60, 2223 (1938). The appropriate sulfonyl chlorides are prepared by several methods. For example, treatment of a substituted aromatic or heterocyclic ring with chlorosulfonic acid in carbon tetrachloride results in the formaton of the sulfonyl chloride. See Clark et al., Org. Synth. Coll., Vol. 1 2nd Ed. 1941, p. 85.

An alternative method of preparation of sulfonyl chlorides can be achieved from an appropriate amine. Diazotization of an amine with sodium nitrite in acid, followed by exposure of the resulting diazonium salt to sulfur dioxide in the presence of cuprous chloride results in the formation of a sulfonyl chloride. See H. L. Yale and F. Sowinski, J. Org. Chem., 25, 1824, (1960).

The heterocyclic amines III where A is A-1 (T=H) or A-5 may be prepared via generation of the lithium anion of VI, followed by addition of the appropriate electrophile, as shown in Equation 3, where E, R, X, Y and Z are as previously defined. R" is H, CH.sub.3, --C(CH.sub.3).sub.2, --CO.sub.2 CH.sub.3 or --CO.sub.2 Ph. ##STR16##

The reaction is generally carried out by adding the heterocycle (VI) to a solution of lithium diisopropylamide (LDA) in tetrahydrofuran at -78.degree. C. followed by the addition of the electrophile (E.sup.+ or Y.sup.+, for example, N-bromosuccinimide or dimethyldiselenide). In the case where R"=CO.sub.2 CH.sub.3 or CO.sub.2 Ph, removal of this group is accomplished by treatment with an aqueous base such as potassium hydroxide in methanol.

A second group, T, may be introduced in several ways. Treatment of the reaction mixture with an excess of LDA followed by sequential addition of electrophiles, Y.sup.+ and T.sup.+, affords the desired dialkylated compound (IIIb) as shown in Equation 4. ##STR17##

Alternatively, the product of addition of Y.sup.+ may be isolated and then retreated as described previously with LDA and T.sup.+ to afford the disubstituted compound (IIIb).

Compounds of Formulas IIIa or IIIb wherein Y is OSi(CH.sub.3).sub.3 or CH.sub.2 OSi(CH.sub.3).sub.3 can be prepared via silylation of the corresponding alcohols.

Reference to the following papers is suggested for further information regarding the preparation of lithiated heterocycles: T. Murray, J. Hay, D. Portlock, J. Wolfe, J. Org. Chem., 39, 595 (1974), J. Stowell, Carbanions in Organic Synthesis, John Wiley and Sons, New York, Chichester, Brisbane, Toronto, Singapore, (1979).

The heterocyclic amines III where A is A-2 are prepared via the sequence described below in Equation 5. R, R" and X.sub.1 are as defined previously. Oxidation of the thioether or selenide and thermal elimination of the resulting sulfoxide or selenoxide affords the target compound IIIc. For a review on thermal elimination of sulfoxides and selenoxides, see. D. J. Clive, Tetrahedron, 34, 1940 (1978), H. Reich, Acc. Chem. Res., 12, 22 (1979), B. M. Trost. T. H. Saltzman, K. Hiroi, J. Am. Chem. Soc., 98, 4887 (1976). ##STR18##

The prerequisite starting heterocycles VI and VIa used in the preparation of A-1, A-2 and A-5 are generally known in the art and are reviewed in The Chemistry of Heterocyclic Compounds, Interscience Publ., New York and London. See D. J. Brown, "The Pyrimidines", Vol. XVI and E. M. Smolin and L. Rapaport, "s-Triazines and Derivatives", Vol. XIII. For additional references, see F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer; J. Org. Chem., 28, 184 (1963).

The heterocyclic amines III where R is a methyl group may be prepared from the corresponding compounds where R is hydrogen by known methods. An example of this type of transformation is described in: J. Chem. Soc. Perkin I, 1569 (1981).

The heterocyclic amines III, where A is A-3 and A-4 are best prepared by the exposure of 1,1,1,5,5,5-hexafluoroacetylacetone to guanidine carbonate in an inert solvent such as DMSO as outlined in Equation 6. ##STR19##

The reaction is best performed at 25.degree. to 125.degree. C. for 1 to 24 hours. The product is usually isolated by pouring the reaction mixture over ice and collecting the resulting solids.

Many of the heterocyclic amines of Formula III in which A is A-1, T is H, Y is as defined previously and q=0 may be prepared by methods known in the art or as described in European Patent Office Publication No. 84,224, published July 27, 1983. For example, when Y is a phenoxy substituent, the known acetoacetic ester VII (U.S. Pat. No. 3,775,467) can be condensed with guanidine carbonate in a suitable solvent such as ethanol preferably above ambient temperature to yield the pyrimidine intermediate VIII, as shown in Equation 7. This can be converted to the chloropyrimidine IX upon treatment with excess phosphorous oxychloride, preferably with heating above ambient temperature. Reaction of IX with an appropriate alkali metal alkoxide in alcohol solvent affords the corresponding alkoxy-substituted pyrimidine of Formula IIIf. ##STR20## wherein R'=CH.sub.3 or C.sub.2 H.sub.5 ; and

M=alkali metal.

The synthesis of heterocyclic amines of Formula III wherein A is A-6 can be accomplished as depicted in Equation 8. An alkali metal salt of the appropriate 4-hydroxypyrimidine or triazine X is prepared from X and a suitable base such as an alkali metal alkoxide, for example potassium t-butoxide, in a polar aprotic solvent such as dimethylformamide (DMF). This salt (XI) is then treated with the appropriate haloacetaldehyde acetal such as 2-bromomethyl-1,3-dioxolane and heated in the range of 50.degree. to 150.degree. C., preferably at 110.degree. to 130.degree. C., for 1 to 24 hours. The desired products are conveniently isolated by chromatography on silica gel to separate them from the unwanted N-alkylated isomers. ##STR21## wherein R, X.sub.1, Z and G are as defined previously;

M is an alkali metal; R' is lower alkyl; and X.sup.2 is halogen.

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydroxide). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The following examples teach the synthesis of some of the compounds contained within this invention in greater detail.

EXAMPLE 1

Methyl(4-fluoromethyl-6-methoxypyrimidin-2-yl)carbamate

To a stirred solution of lithium diisopropylamide (8.3 mmol) in tetrahydrofuran at -78.degree. C. was added (4-methyl-6-methoxypyrimidin-2-yl)carbamic acid, methyl ester (4.16 mmol). The solution was stirred at -78.degree. C., then N-fluoro-N-2,2-dimethylpropyl-p-toluenesulfonamide (4.6 mmol) in THF was added dropwise. The solution was stirred an additional 1 hour then quenched with brine. A crystalline product was collected, 0.71 g, m.p. 98.degree.-102.degree. C. NMR (90 MHz, CDCl.sub.3): .delta. 4.0 (s, 3H); 4.1 (s, 3H); 5.5 (d, 2H); 1.8 (s, 1H); 8.2 (s, 1H).

EXAMPLE 2

4-Methoxy-6-(phenoxymethyl)-2-pyrimidinamine

A mixture of 7.8 g (36 mmol) of ethyl 2-oxo-4-phenoxybutanoate and 3.4 g (38 mmol) guanidine carbonate was heated to reflux in 100 ml abs. ethanol for 48 hours. Filtration of the cooled suspension afforded 4.6 g of 2-amino-4-hydroxy-6-phenoxymethylpyrimidine in two crops, m.p. 253.degree.-254.degree. (dec). This intermediate (4.3 g, 20 mmol) was heated to reflux in 50 ml phosphorous oxychloride for 2 hours then evaporated. The residue was treated with ice-water and neutralized with 10% sodium hydroxide solution then extracted with chloroform. Evaporation of the extracts left a residue which was purified by dissolution in 15% ethyl acetate/methylene chloride and filtration through silica gel. The filtrate was concentrated and crystallized from ether/1-chlorobutane/hexanes to yield 0.65 g of 2-amino-4-chloro-6-phenoxymethylpyrimidine, m.p. 123.degree.-124.degree.. An additional 0.8 g was deposited from the original aqueous phase, m.p. 118.degree.-121.degree., for a total of 1.4 g of product. A 1.0 g (4.2 mmol) portion of this material was reacted with 20 mmol sodium methoxide in 30 ml methanol at reflux for 2 hours, then concentrated in vacuo. The residue was triturated with water, collected, water rinsed and dried to 0.9 g of the title compound, m.p. 94.degree.-96.degree.. NMR (90 MHz, CDCl.sub.3): .delta. 3.83 (s, 3H); 4.90 (s, 2H); 6.31 (s, 1H); 6.9-7.1 (m, 3H); 7.22-7.45 (m, 2H) ppm.

EXAMPLE 3

4-Ethylidene-6-methoxy-2-pyrimidinamine

To a stirring solution of 4-methoxy-6-[1-(phenylselenyl)ethyl]-2-pyrimidinamine (14.3 mmol) in 100 ml of CH.sub.2 Cl.sub.2 cooled to -78.degree. C. was added in one portion m-chloroperbenzoic acid (14.3 mmol). The solution was warmed to room temperature, diluted with ether and filtered. A white crystalline solid (0.17 g), m.p. 119.degree.-122.degree. C. was isolated. NMR (200 MHz, CDCl.sub.3) .delta. 3.87 (s, 3H); 5.9 (br s, 2H); 5.5 (d, d, 1H); 6.0 (s, 1H); 6.2-6.6 (m, 2H).

EXAMPLE 4

4-Methoxy-6-phenylselenylmethyl-2-pyrimidinamine

To a stirring solution of lithium diisopropylamide (203 mmol) in tetrahydrofuran, cooled to -78.degree. C. was added methyl(4-methyl-6-methoxypyrimidin-2-yl)carbamate (50.7 mmol). After stirring one hour at -78.degree. C. phenyl diselenide (50.7 mmol) was added, stirred an additional 30 minutes, followed by the addition of methyl iodide (50.7 mmol). The reaction mixture was warmed to -30.degree. C., quenched with brine, the organic phase separated, dried and concentrated. The resulting oil was filtered through a column of silica gel to give 13.3 g of an oil. The crude oil (12.2 g) was dissolved in 206 ml of methanol and 9.4 ml of water, potassium hydroxide (105 mmol) was added and the solution was refluxed for 3 hours. The reaction mixture was cooled to 0.degree. C., neutralized to pH 7 with concentrated HCl and extracted with ethyl acetate. The crude product was flash chromatographed with ether/hexane (35:65) to yield 3 products. Product 1 (0.24 g), the title compound, was obtained as a solid with m.p. 115.degree.-117.degree. C., NMR (60 MHz, CDCl.sub.3): .delta. 3.9 (s, 2H); 4.0 (s, 3H); 5.2 (br. s, 2H); 6.0 (s, 1H); 7.2-7.5 (m, 5H). Product 2 (1.3 g), 4-methoxy-6-[1-methyl-1-(phenylselenyl)ethyl]- 2-pyrimidinamine, m.p. 104.degree.-106.degree. C., was the dimethylated product. NMR (200 MHz, CDCl.sub.3): .delta. 1.7 (s, 6H); 3.9 (s, 3H); 5.2 (br. s, 2H); 6.8 (s, 1H); 7.3 (m, 5H). Product 3 (4.6 g) was the mono methylated aminopyrimidine of Formula III in which A is A-1 (X=OCH.sub.3, Y=SePh, T=CH.sub.3, Z=CH, R=H).

EXAMPLE 5

Methyl[4-methoxy-6-(phenylthiomethyl)pyrimidin-2-yl]carbamate

To a stirring solution of lithium diisopropylamide (126.9 mmol) in 400 ml of tetrahydrofuran at -78.degree. C. was added methyl(4-methyl-6-methoxypyrimidin-2-yl)carbamate (50.8 mmol). After stirring one hour at -78.degree. C., phenyl disulfide (127 mmol) was added. Work-up with brine afforded 30 g of a crude oil. Flash chromatography of the crude product with ether/hexane (50:50) gave two products. Product 1 (5.6 g) a clear oil, was the desired product (A-1, X=OCH.sub.3, Y=H, Z=CH, T=SPh), NMR (60 MHz, CDCl.sub.3): .delta. 3.9 (s, 3H); 4.0 (s, 3H); 4.2 (s, 2H); 6.5 (s, 1H); 7.3 (m, 5H); 8.2 (br. s, 1H). Product 2 (1.2 g) was the dithiolated carbamate of Formula V in which R' is CH.sub.3, R is H, and A is A-1 (X=OCH.sub.3, Y=SPh, Z=CH, T=SPh). NMR (60 MHz, CDCl.sub.3): .delta. 3.7 (s, 3H); 3.9 (s, 3H); 5.4 (s, 1H); 6.4 (s, 1H); 7.0-7.5 (m, 10H); 8.4 (br. s, 1H).

EXAMPLE 6

4-Methoxy-6-(methylselenylmethyl)-2-pyrimidinamine

To a stirring solution of potassium hydroxide (15.6 mmol) in H.sub.2 O (77.5 mmol) and 50 ml of methanol was added methyl[4-methoxy-6-(methylselenylmethyl)pyrimidin-2-yl]carbamate (5.2 mmol). The solution was heated to the reflux point for 3 hours, then cooled to 0.degree. C. The solution was neutralized to pH7 with concentrated HCl and then the solvent was removed under reduced pressure. The resulting residue was washed with THF to afford 1.3 g, m.p. 88.degree.-91.degree. C.; NMR (200 MHz, CDCl.sub.3): .delta. 2.01 (s, 3H); 3.48 (s, 2H); 3.85 (s, 3H); 5.1 (br. s, 2H); 5.99 (s, 1H).

EXAMPLE 7

4,6-Bis(trifluoromethyl)-2-pyrimidinamine

A mixture of guanidine carbonate (180 mmol) and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione (120 mmol) was dissolved in 60 ml of DMSO and warmed to 110.degree. C. for 2 to 3 hours. Flash chromatography of the crude reaction product with ether/hexane (50:50) afforded 13.8 g of the title compound as a white crystalline solid, m.p. 94.5.degree.-96.degree. C. NMR (60 MHz, CDCl.sub.3): .delta. 6.5 (br. s, 2H); 7.2 (s, 1H). A second product isolated was the hydroxypyrimidine (A is A-3): m.p. 116.degree.-118.5.degree. C. NMR (90 MHz, CDCl.sub.3): .delta. 7.1 (br. s, 3H); 7.3 (s, 1H).

EXAMPLE 8

Methyl 2-[[[(4-methoxy-6-(phenylselenylmethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate

To a stirring solution of 4-methoxy-6-(phenylselenylmethyl)-2-pyrimidinamine (0.67 mmol) in 25 ml of methylene chloride was added o-carbomethoxybenzenesulfonyl isocyanate (0.84 mmol). The solution was stirred for 16 hours at room temperature and concentrated. The resulting solid was washed with butyl chloride to afford 0.25 g of the desired product, m.p. 134.degree.-139.degree. C. NMR (200 MHz, CDCl.sub.3): .delta. 3.90 (s, 3H); 3.95 (s, 3H); 4.1 (s, 2H); 6.1 (s, 1H); 7.3 (m, 3H); 1.5 (m, 3H); 7.7 (m, 3H); 8.3 (m, 1H); 12.8 (br. s, 1H).

EXAMPLE 9

Methyl 2-[[[4-(fluoromethyl)-6-methylpyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate

To a stirring solution of 4-methyl-6-fluoromethyl-2-pyrimidinamine (1.4 mmol) in 25 ml of CH.sub.2 Cl.sub.2 was added o-carbomethoxybenzenesulfonyl isocyanate (1.77 mmol). After stirring 16 hours the reaction was concentrated and the resulting solid washed with butyl chloride to afford 0.28 g of the desired product, m.p. 181.degree.-186.degree. C. NMR (90 MHz, CDCl.sub.3): .delta. 2.5 (s, 3H); 4.0 (s, 3H); 5.2 (s, 1H); 5.7 (s, 1H); 7.0 (s, 1H); 7.6 (m, 3H); 8.2 (m, 1H); 10.3 (s, 1H); 12.8 (br. s, 1H).

EXAMPLE 10

Methyl 2-[[[bis(4,6-trifluoromethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate

To a stirring solution of 4,6-bis(trifluoromethyl)-2-pyrimidinamine (2.16 mmol) in 25 ml of methylene chloride was added o-carbomethoxybenzenesulfonyl isocyanate (2.38 mmol). After stirring 10 hours at room temperature the reaction was concentrated and the resulting solid was washed with butyl chloride to afford 0.36 g of the title compound, m.p. 153.degree.-161.degree. C. NMR (90 MHz, CDCl.sub.3): .delta. 4.0 (s, 3H); 7.5-7.8 (m, 4H); 8.3-8.4 (m, 1H); 11.0-11.6 (br. s, 2H).

EXAMPLE 11

Methyl 2-[[[4-Methoxy-6-(phenoxymethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate

To a mixture of 0.23 g (1.0 mmol) of 4-methoxy-6-(phenoxymethyl)-2-pyrimidinamine in 15 ml dry acetonitrile was added 0.48 g (2.0 mmol) o-carbomethoxybenzenesulfonyl isocyanate and stirred at ambient temperature overnight. Ether was added to the suspension of white solids which were then collected by filtration to afford 0.37 g of the title compound, m.p. 178.degree.-180.degree.. NMR (90 MHz, CDCl.sub.3 +DMSO-d.sub.6): .delta. 3.91 (s, 3H); 4.02 (s, 3H); 5.20 (s, 2H); 6.69 (s, 1H); 7.0-7.9 (m, 8H); 8.5 (m, 1H); 9.20 (s, NH); 12.9 (s, NH) ppm; IR (nujol) 1725, 1700 cm.sup.-1.

EXAMPLE 12

4-(1,3-Dioxolan-2-ylmethoxy)-6-methoxy-2-pyrimidinamine

A solution of 8.5 g (0.060 mol) 2-amino-6-methyl-4-pyrimidinone in 45 mL anhydrous dimethylformamide (DMF) was treated with 6.7 g (0.060 mol) potassium t-butoxide then stirred for 10 minutes at ambient temperature. Subsequently, 7.6 mL (0.073 mol) of 2-bromomethyl-1,3-dioxolane was added and the mixture heated to 120.degree. for 3 hours. The DMF was then evaporated under reduced pressure and the residue partitioned between water and ethyl acetate. The aqueous phase was extracted with two additional portions of ethyl acetate then the combined organic phase was washed with water, brine, then dried (MgSO.sub.4) and evaporated to an oil. Chromatography on silica gel with 10% ethyl acetate/CH.sub.2 Cl.sub.2 as the eluant afforded 2.3 g of the title compound as a viscous oil. NMR (CDCl.sub.3): .delta. 3.9 (s, 3H), 4.0 (m, 4H), 4.3 (d, J=4 Hz, 2H), 5.15 (NH, br), 5.27 (t, J=4 Hz, 1H), 5.55 (s, 1H) ppm.

EXAMPLE 13

Methyl 2-[[[4-(1,3-Dioxolan-2-ylmethoxy)-6-methoxypyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate

A solution of the aminopyrimidine of the preceding example (0.5 g, 2.2 mmol) was dissolved in 10 mL dry acetonitrile then treated with 0.6 g (2.4 mmol) of 2-carbomethoxybenzenesulfonyl isocyanate. The mixture was warmed briefly then stirred at ambient temperature for several hours and subsequently evaporated to dryness. Trituration of the residue with ether afforded 0.85 g of the title compound as colorless crystals, m.p. 102.degree.-104.degree. (dec.). NMR (200 MHz, CDCl.sub.3): .delta. 3.90 (s, 3H), 4.05 (s, 3H), 3.95 (m, 4H), 4.39 (d, J=4 Hz, 2H), 5.26 (t, J=4 Hz, 1H), 5.85 (s, 1H), 7.2 (NH, br), 7.68 (m, 3H), 8.45 (m, 1H), 12.4 (NH, br) ppm; IR (nujol) 1715, 1730 cm.sup.-1.

Using the procedures of Examples 1-13 the following compounds may be prepared.

TABLE 1a__________________________________________________________________________ ##STR22##R.sub.1 R.sub.2 R X T Y Z m.p. (.degree.C.)__________________________________________________________________________H H H OCH.sub.3 H SPh CHH H H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 H H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 H H CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 H H CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 H SOPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 H SO.sub.2 Ph CHCO.sub. 2 CH.sub.3 H H CH.sub.3 H OPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 H H CH.sub.3 SeCH.sub.3 SePh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SeCH.sub.3 SPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SeCH.sub.3 SOPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SeCH.sub.3 SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H H CH.sub.3 SePh SeCH.sub.3 CHCO.sub.2 CH.sub.3 H H CH.sub.3 SePh SePh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SePh Sph CHCO.sub.2 CH.sub.3 H H CH.sub.3 SePh SOPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SePh SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SePh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SOPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 OPh CHCO.sub.2 CH.sub.3 H H CH.sub.3 H ##STR23## CHCO.sub.2 CH.sub.3 H H CH.sub.3 H ##STR24## CHCO.sub.2 CH.sub.3 H H CH.sub.3 H ##STR25## CHCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 SPh SPh CHCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 H OPh CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 3-OCH.sub.3 H CH.sub. 3 H SPh CHCO.sub.2 CH.sub.3 6-OCH.sub.3 H CH.sub.3 H SOPh CHCO.sub.2 CH.sub.3 6-OCH.sub.3 H CH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H CH.sub.3 H OPh CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 3-OCH.sub.3 H CH.sub.3 SeCH.sub.3 SePh CHCO.sub.2 CH.sub.3 3-OCH.sub.3 H CH.sub.3 SeCH.sub.3 SPh CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H CH.sub.3 SeCH.sub.3 SO.sub.2 Ph CHCO.sub.2 CH.sub.3 3-CF.sub.3 H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 5-CF.sub.3 H CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 6-CF.sub.3 H CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 6-CF.sub.3 H CH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 5-CF.sub.3 H CH.sub.3 H OPh CHCO.sub.2 CH.sub.3 5-CF.sub.3 H CH.sub.3 SPh SPh CHCO.sub.2 CH.sub.3 3-Cl H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 5-Cl H CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 6-Cl H CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 6-Cl H CH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 5-Br H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 5-Br H CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 6-Br H CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 3-F H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 3-F H CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 3-F H CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 5-F H CH.sub.3 H SOPh CHCO.sub.2 CH.sub.3 6-F H CH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 6-F H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 3-F H CH.sub.3 SePh SePh CHCO.sub.2 CH.sub.3 5-F H CH.sub.3 SPh SPh CHCO.sub.2 CH.sub.3 5-CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 6-CH.sub.3 H CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CH 144-147CO.sub.2 CH.sub.3 H H OCH.sub.3 H SePh CH 134-139CO.sub.2 CH.sub.3 H H OCH.sub.3 H SPh CH 149-152CO.sub.2 CH.sub.3 H H OCH.sub.3 H SOPh CH 176-178.5CO.sub.2 CH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H H OCH.sub.3 H OPh CH 178-180CO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SePh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SOPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SeCH.sub.3 CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SePh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SPh SPh CH 125-127CO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SOPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SePh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SOPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 OPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 H ##STR26## CHCO.sub.2 CH.sub.3 H H OCH.sub.3 H ##STR27## CHCO.sub.2 CH.sub.3 H H OCH.sub.3 H ##STR28## CHCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 SPh SPh CHCO.sub.2 CH.sub. 3 H CH.sub.3 OCH.sub.3 H OPh CHCO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 H SOPh CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 H OPh CHCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SePh CHCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SPh CHCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SO.sub.2 Ph CHCO.sub.2 CH.sub.3 3-CF.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 3-CF.sub.3 H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H OPh CHCO.sub.2 CH.sub.3 6-CF.sub.3 H OCH.sub.3 SPh SPh CHCO.sub.2 CH.sub.3 3-Cl H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 3-Cl H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 3-Cl H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 5-Cl H OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 5-Br H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 5-Br H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 5-Br H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 6-F H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 6-F H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 3-F H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 5-F H OCH.sub.3 H SOPh CHCO.sub.2 CH.sub.3 6-F H OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 3-F H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.3 5-F H OCH.sub.3 SePh SePh CHCO.sub.2 CH.sub.3 6-F H OCH.sub.3 SPh SPh CHCO.sub.2 CH.sub.3 3-CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 5-CH.sub.3 H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H H OCH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 H H CH.sub.3 H SePh NCO.sub.2 CH.sub.3 H H Cl H OPh CH 195-197CO.sub.2 CH.sub.3 H H OCH.sub.3 H SPh NCO.sub.2 CH.sub.3 H H CH.sub.3 H SOPh NCO.sub.2 CH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph NCO.sub.2 CH.sub.3 H H CH.sub.3 H OPh NCO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NCO.sub.2 CH.sub.3 H H CH.sub.3 SeCH.sub.3 SePh NCO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SPh NCO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SOPh NCO.sub.2 CH.sub.3 H H CH.sub.3 SeCH.sub.3 SO.sub.2 Ph NCO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SeCH.sub.3 NCO.sub.2 CH.sub.3 H H CH.sub.3 SePh SePh NCO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SPh NCO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SOPh NCO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SO.sub.2 Ph NCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 NCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SePh NCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SPh NCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SOPh NCO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SO.sub.2 Ph NCO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 OPh NCO.sub.2 CH.sub.3 H H OCH.sub.3 H ##STR29## NCO.sub.2 CH.sub.3 H H OCH.sub.3 H ##STR30## NCO.sub.2 CH.sub.3 H H OCH.sub.3 H ##STR31## NCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SePh NCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SPh NCO.sub. 2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SO.sub.2 Ph NCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 SPh SPh NCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H OPh NCO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SePh NCO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh NCO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 H SOPh NCO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 H SO.sub.2 Ph NCO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 H OPh NCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SePh NCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SPh NCO.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SO.sub.2 Ph NCO.sub.2 CH.sub.3 3-CF.sub.3 H OCH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 3-CF.sub.3 H OCH.sub.3 H SePh NCO.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh NCO.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H SO.sub.2 Ph NCO.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H OPh NCO.sub.2 CH.sub.3 6-CF.sub.3 H OCH.sub.3 SPh SPh NCO.sub.2 CH.sub.3 3-Cl H OCH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 3-Cl H CH.sub.3 H SePh NCO.sub.2 CH.sub.3 3-Cl H OCH.sub.3 H SPh NCO.sub.2 CH.sub.3 5-Cl H CH.sub.3 H SO.sub.2 Ph NCO.sub.2 CH.sub.3 5-Br H OCH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 5-Br H CH.sub.3 H SePh NCO.sub.2 CH.sub.3 5-Br H OCH.sub.3 H SPh NCO.sub.2 CH.sub.3 6-F H CH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 6-F H OCH.sub.3 H SePh NCO.sub.2 CH.sub.3 3-F H CH.sub.3 H SPh NCO.sub.2 CH.sub.3 5-F H OCH.sub.3 H SOPh NCO.sub.2 CH.sub.3 6-F H CH.sub.3 H SO.sub.2 Ph NCO.sub.2 CH.sub.3 3-F H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NCO.sub.2 CH.sub.3 5-F H CH.sub.3 SePh SePh NCO.sub.2 CH.sub.3 6-F H OCH.sub.3 SPh SPh NCO.sub.2 CH.sub.3 3-CH.sub.3 H CH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 5-CH.sub.3 H OCH.sub.3 H SPh NCl H H OCH.sub.3 H SeCH.sub.3 CH 134-140Cl H H OCH.sub.3 H SPh CH 184-186Cl H H CH.sub.3 H SePh CHCl H H OCH.sub.3 H SOPh CH 148-152Cl H H CH.sub.3 SPh SPh CHCl H H OCH.sub.2 CH.sub.3 H SPh CHCl H H OCH.sub.3 SePh SePh CHCl H H Br H SePh CHCl H H OCH.sub.3 H OPh CH 196-198Cl H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCl H H OCH.sub.3 H SPh NCl H H OCF.sub.2 H H SPh CHCl H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHCl H H OCH.sub.3 SPh SPh NCl H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NCl H H F H SPh CHCl H H OCH.sub.3 SPh SPh CH 174-175.5Cl H H CF.sub.3 H SeCH.sub.3 CHCl H H CF.sub.3 H SPh CHCl H H OCH.sub.3 H OPh NCl H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NCl H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCl H CH.sub.3 OCH.sub.3 H SPh CHCl 5-OCH.sub.3 H OCH.sub.3 H SPh CHCl 5-CF.sub.3 H OCH.sub.3 H SPh CHCl 3-F H OCH.sub.3 H SePh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 H SeCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 H SPh CH 166-168SO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 H SePh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 H SO.sub.2 Ph CHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 SPh SPh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.2 CH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 SePh SePh CHSO.sub.2 N(CH.sub.3).sub.2 H H Br H SePh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 H OPh CH 222-224SO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 H SPh NSO.sub.2 N(CH.sub.3).sub.2 H H OCF.sub.2 H H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 SPh SPh NSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NSO.sub.2 N(CH.sub.3).sub.2 H H F H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 SPh SPh CHSO.sub.2 N(CH.sub.3).sub.2 H H CF.sub.3 H SeCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 H H CF.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 H OPh NSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSO.sub. 2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 5-OCH.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 5-CF.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 3-F H OCH.sub.3 H SePh CHNO.sub.2 H H OCH.sub.3 H SeCH.sub.3 CHNO.sub.2 H H OCH.sub.3 H SPh CHNO.sub.2 H H CH.sub.3 H SePh CHNO.sub.2 H H OCH.sub.3 H SO.sub.2 Ph CHNO.sub.2 H H CH.sub.3 SPh SPh CHNO.sub.2 H H OCH.sub.2 CH.sub.3 H SPh CHNO.sub.2 H H OCH.sub.3 SePh SePh CHNO.sub.2 H H Br H SePh CHNO.sub.2 H H OCH.sub.3 H OPh CHNO.sub.2 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHNO.sub.2 H H OCH.sub.3 H SPh NNO.sub.2 H H OCF.sub.2 H H SPh CHNO.sub.2 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHNO.sub.2 H H OCH.sub.3 SPh SPh NNO.sub.2 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NNO.sub.2 H H F H SPh CHNO.sub.2 H H OCH.sub.3 SPh SPh CHNO.sub.2 H H CF.sub.3 H SeCH.sub.3 CHNO.sub.2 H H CF.sub.3 H SPh CHNO.sub.2 H H OCH.sub.3 H OPh NNO.sub.2 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NNO.sub.2 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHNO.sub.2 H CH.sub.3 OCH.sub.3 H SPh CHNO.sub.2 5-OCH.sub.3 H OCH.sub.3 H SPh CHNO.sub.2 5-CF.sub.3 H OCH.sub.3 H SPh CHNO.sub.2 3-F H OCH.sub.3 H SePh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHSO.sub.2 CH.sub.3 H H OCH.sub.3 H SPh CHSO.sub.2 CH.sub.3 H H CH.sub.3 H SePh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHSO.sub.2 CH.sub.3 H H CH.sub.3 SPh SPh CHSO.sub.2 CH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 SePh SePh CHSO.sub.2 CH.sub.3 H H Br H SePh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 H OPh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSO.sub.2 CH.sub.3 H H OCH.sub.3 H SPh NSO.sub.2 CH.sub.3 H H OCF.sub.2 H H SPh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHSO.sub.2 CH.sub.3 H H OCH.sub.3 SPh SPh NSO.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NSO.sub.2 CH.sub.3 H H F H SPh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 SPh SPh CHSO.sub.2 CH.sub.3 H H CF.sub.3 H SeCH.sub.3 CHSO.sub.2 CH.sub.3 H H CF.sub.3 H SPh CHSO.sub.2 CH.sub.3 H H OCH.sub.3 H OPh NSO.sub.2 CH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NSO.sub.2 CH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHSO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 CH.sub.3 3-F H OCH.sub.3 H SePh CHCF.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHCF.sub.3 H H OCH.sub.3 H SPh CHCF.sub.3 H H CH.sub.3 H SePh CHCF.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHCF.sub.3 H H CH.sub.3 SPh SPh CHCF.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHCF.sub.3 H H OCH.sub.3 SePh SePh CHCF.sub.3 H H Br H SePh CHCF.sub.3 H H OCH.sub.3 H OPh CHCF.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCF.sub.3 H H OCH.sub.3 H SPh NCF.sub.3 H H OCF.sub.2 H H SPh CHCF.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHCF.sub.3 H H OCH.sub.3 SPh SPh NCF.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NCF H H F H SPh CHCF.sub.3 H H OCH.sub.3 SPh SPh CHCF.sub.3 H H CF.sub.3 H SeCH.sub.3 CHCF.sub.3 H H CF.sub.3 H SPh CHCF.sub.3 H H OCH.sub.3 H OPh NCF.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NCF.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCF.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHCF.sub.3 5-OCH.sub.3 H OCH.sub.3 H SPh CH -CF.sub.3 3-CF.sub.3 H OCH.sub.3 H SPh CH 1CF.sub.3 6-F H OCH.sub.3 H SePh CHCH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHCH.sub.3 H H OCH.sub.3 H SPh CHCH.sub.3 H H CH.sub.3 H SePh CHCH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHCH.sub.3 H H CH.sub.3 SPh SPh CHCH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHCH.sub.3 H H OCH.sub.3 SePh SePh CHCH.sub.3 H H Br H SePh CHCH.sub.3 H H OCH.sub.3 H OPh CHCH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 H H OCH.sub.3 H SPh NCH.sub.3 H H OCF.sub.2 H H SPh CHCH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHCH.sub.3 H H OCH.sub.3 SPh SPh NCH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NCH.sub.3 H H F H SPh CHCH.sub.3 H H OCH.sub.3 SPh SPh CHCH.sub.3 H H CF.sub.3 H SeCH.sub.3 CHCH.sub.3 H H CF.sub.3 H SPh CHCH.sub.3 H H OCH.sub.3 H OPh NCH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NCH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHCH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHCH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHCH.sub.3 6-F H OCH.sub.3 H SePh CHOCH.sub.2 CCH H H OCH.sub.3 H SeCH.sub.3 CHOCH.sub.2 CCH H H OCH.sub.3 H SPh CHOCH.sub.2 CCH H H CH.sub.3 H SePh CHOCH.sub.2 CCH H H OCH.sub.3 H SO.sub.2 Ph CHOCH.sub.2 CCH H H CH.sub.3 SPh SPh CHOCH.sub.2 CCH H H OCH.sub.2 CH.sub.3 H SPh CHOCH.sub.2 CCH H H OCH.sub.3 SePh SePh CHOCH.sub.2 CCH H H Br H SePh CHOCH.sub.2 CCH H H OCH.sub.3 H OPh CHOCH.sub.2 CCH H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.2 CCH H H OCH.sub.3 H SPh NOCH.sub.2 CCH H H OCF.sub.2 H H SPh CHOCH.sub.2 CCH H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHOCH.sub.2 C CH H H OCH.sub.3 SPh SPh NOCH.sub.2 CCH H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NOCH.sub.2 CCH H H F H SPh CHOCH.sub.2 CCH H H OCH.sub.3 SPh SPh CHOCH.sub.2 CCH H H CF.sub.3 H SeCH.sub.3 CHOCH.sub.2 CCH H H CF.sub.3 H SPh CHOCH.sub.2 CCH H H OCH.sub.3 H OPh NOCH.sub.2 CCH H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NOCH.sub.2 CCH H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.2 CCH H CH.sub.3 OCH.sub.3 H SPh CHOCH.sub.2 CCH 3-OCH.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2 CCH 5-CF.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2 CCH 6-F H OCH.sub.3 H SePh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 H SeCH.sub.3 CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 H SPh CHOCH.sub.2CHCH.sub.2 H H CH.sub.3 H SePh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 H SO.sub.2 Ph CHOCH.sub.2CHCH.sub.2 H H CH.sub.3 SPh SPh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.2 CH.sub.3 H SPh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 SePh SePh CHOCH.sub.2CHCH.sub.2 H H Br H SePh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 H OPh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 H SPh NOCH.sub.2CHCH.sub.2 H H OCF.sub.2 H H SPh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 SPh SPh NOCH.sub.2CHCH.sub.2 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NOCH.sub.2CHCH.sub.2 H H F H SPh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 SPh SPh CHOCH.sub.2CHCH.sub.2 H H CF.sub.3 H SeCH.sub.3 CHOCH.sub.2CHCH.sub.2 H H CF.sub.3 H SPh CHOCH.sub.2CHCH.sub.2 H H OCH.sub.3 H OPh NOCH.sub.2CHCH.sub.2 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NOCH.sub.2CHCH.sub.2 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.2CHCH.sub.2 H CH.sub.3 OCH.sub.3 H SPh CHOCH.sub.2CHCH.sub.2 3-OCH.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2CHCH.sub.2 6-CF.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2CHCH.sub.2 5-F H OCH.sub.3 H SePh CHOCF.sub.3 H H OCH.sub. 3 H SeCH.sub.3 CHOCF.sub.3 H H OCH.sub.3 H SPh CHOCF.sub.3 H H CH.sub.3 H SePh CHOCF.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHOCF.sub.3 H H CH.sub.3 SPh SPh CHOCF.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHOCF.sub.3 H H OCH.sub.3 SePh SePh CHOCF.sub.3 H H Br H SePh CHOCF.sub.3 H H OCH.sub.3 H OPh CHOCF.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCF.sub.3 H H OCH.sub.3 H SPh NOCF.sub.3 H H OCF.sub.2 H H SPh CHOCF.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHOCF.sub.3 H H OCH.sub.3 SPh SPh NOCF.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NOCF.sub.3 H H F H SPh CHOCF.sub.3 H H OCH.sub.3 SPh SPh CHOCF.sub.3 H H CF.sub.3 H SeCH.sub.3 CHOCF.sub.3 H H CF.sub.3 H SPh CHOCF.sub.3 H H OCH.sub.3 H OPh NOCF.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NOCF.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCF.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHOCF.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHOCF.sub.3 6-CF.sub.3 H OCH.sub.3 H SPh CHOCF.sub.3 5-F H OCH.sub.3 H SePh CHOCHF.sub.2 H H OCH.sub.3 H SeCH.sub.3 CHOCHF.sub.2 H H OCH.sub.3 H SPh CHOCHF.sub.2 H H CH.sub.3 H SePh CHOCHF.sub.2 H H OCH.sub.3 H SO.sub.2 Ph CHOCHF.sub.2 H H CH.sub.3 SPh SPh CHOCHF.sub.2 H H OCH.sub.2 CH.sub.3 H SPh CHOCHF.sub.2 H H OCH.sub.3 SePh SePh CHOCHF.sub.2 H H Br H SePh CHOCHF.sub.2 H H OCH.sub.3 H OPh CHOCHF.sub.2 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCHF.sub.2 H H OCH.sub.3 H SPh NOCHF.sub.2 H H OCF.sub.2 H H SPh CHOCHF.sub.2 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHOCHF.sub.2 H H OCH.sub.3 SPh SPh NOCHF.sub.2 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NOCHF.sub.2 H H F H SPh CHOCHF.sub.2 H H OCH.sub.3 SPh SPh CHOCHF.sub.2 H H CF.sub.3 H SeCH.sub.3 CHOCHF.sub.2 H H CF.sub.3 H SPh CHOCHF.sub.2 H H OCH.sub.3 H OPh NOCHF.sub.2 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NOCHF.sub.2 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCHF.sub.2 H CH.sub.3 OCH.sub.3 H SPh CHOCHF.sub.2 3-OCH.sub.3 H OCH.sub.3 H SPh CHOCHF.sub.2 5-CF.sub.3 H OCH.sub.3 H SPh CHOCHF.sub.2 6-F H OCH.sub.3 H SePh CHSCHF.sub.2 H H OCH.sub.3 H SeCH.sub.3 CHSCHF.sub.2 H H OCH.sub.3 H SPh CHSCHF.sub.2 H H CH.sub.3 H SePh CHSCHF.sub.2 H H OCH.sub.3 H SO.sub.2 Ph CHSCHF.sub.2 H H CH.sub.3 SPh SPh CHSCHF.sub.2 H H OCH.sub.2 CH.sub.3 H SPh CHSCHF.sub.2 H H OCH.sub.3 SePh SePh CHSCHF.sub.2 H H Br H SePh CHSCHF.sub.2 H H OCH.sub.3 H OPh CHSCHF.sub.2 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSCHF.sub.2 H H OCH.sub.3 H SPh NSCHF.sub.2 H H OCF.sub.2 H H SPh CHSCHF.sub.2 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHSCHF.sub.2 H H OCH.sub.3 SPh SPh NSCHF.sub.2 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NSCHF.sub.2 H H F H SPh CHSCHF.sub.2 H H OCH.sub.3 SPh SPh CHSCHF.sub.2 H H CF.sub.3 H SeCH.sub.3 CHSCHF.sub.2 H H CF.sub.3 H SPh CHSCHF.sub.2 H H OCH.sub.3 H OPh NSCHF.sub.2 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NSCHF.sub.2 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSCHF.sub.2 H CH.sub.3 OCH.sub.3 H SPh CHSCHF.sub.2 3-OCH.sub.3 H OCH.sub.3 H SPh CHSCHF.sub.2 5-CF.sub.3 H OCH.sub.3 H SPh CHSCHF.sub.2 6-F H OCH.sub.3 H SePh CHSCH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHSCH.sub.3 H H OCH.sub.3 H SPh CHSCH.sub.3 H H CH.sub.3 H SePh CHSCH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHSCH.sub. 3 H H CH.sub.3 SPh SPh CHSCH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHSCH.sub.3 H H OCH.sub.3 SePh SePh CHSCH.sub.3 H H Br H SePh CHSCH.sub.3 H H OCH.sub.3 H OPh CHSCH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSCH.sub.3 H H OCH.sub.3 H SPh NSCH.sub.3 H H OCF.sub.2 H H SPh CHSCH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHSCH.sub.3 H H OCH.sub.3 SPh SPh NSCH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NSCH.sub.3 H H F H SPh CHSCH.sub.3 H H OCH.sub.3 SPh SPh CHSCH.sub.3 H H CF.sub.3 H SeCH.sub.3 CHSCH.sub.3 H H CF.sub.3 H SPh CHSCH.sub.3 H H OCH.sub.3 H OPh NSCH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NSCH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSCH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHSCH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHSCH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHSCH.sub.3 6-F H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H SPh CH 105-109CO.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 H SePh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 SPh SPh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 SePh SePh CHCO.sub.2 CH.sub.2 CH.sub.3 H H Br H SePh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H OPh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H SPh NCO.sub.2 CH.sub.2 CH.sub.3 H H OCF.sub.2 H H SPh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub. 3 H H OCH.sub.3 SPh SPh NCO.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NCO.sub.2 CH.sub.2 CH.sub.3 H H F H SPh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 SPh SPh CHCO.sub.2 CH.sub.2 CH.sub.3 H H CF.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 H H CF.sub.3 H SPh CHCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H OPh NCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHCO.sub.2 CH.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.2 CH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 H SePh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H CH.sub.3 H SePh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H CH.sub.3 SPh SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 SePh SePh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H Br H SePh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 H OPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 H SPh NOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCF.sub.2 H H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 SPh SPh NOCH.sub.2 CH.sub.2 OCH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NOCH.sub.2 CH.sub.2 OCH.sub.3 H H F H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 SPh SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H CF.sub.3 H SeCH.sub.3 CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H CF.sub.3 H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 H OPh NOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NOCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2 CH.sub.2 OCH.sub.3 6-F H OCH.sub.3 H SePh CHBr H H OCH.sub.3 H SeCH.sub.3 CHBr H H OCH.sub.3 H SPh CHBr H H CH.sub.3 H SePh CHBr H H OCH.sub.3 H SO.sub.2 Ph CHBr H H CH.sub.3 SPh SPh CHBr H H OCH.sub.2 CH.sub.3 H SPh CHBr H H OCH.sub.3 SePh SePh CHBr H H Br H SePh CHBr H H OCH.sub.3 H OPh CHBr H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHBr H H OCH.sub.3 H SPh NBr H H OCF.sub.2 H H SPh CHBr H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHBr H H OCH.sub.3 SPh SPh NBr H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NBr H H F H SPh CHBr H H OCH.sub.3 SPh SPh CHBr H H CF.sub.3 H SeCH.sub.3 CHBr H H CF.sub.3 H SPh CHBr H H OCH.sub.3 H OPh NBr H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NBr H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHBr H CH.sub.3 OCH.sub.3 H SPh CHBr 3-OCH.sub.3 H OCH.sub.3 H SPh CHBr 5-CF.sub.3 H OCH.sub.3 H SPh CHBr 6-F H OCH.sub.3 H SePh CHOCH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHOCH.sub.3 H H OCH.sub.3 H SPh CHOCH.sub.3 H H CH.sub.3 H SePh CHOCH.sub.3 H H OCH.sub.3 H SO.sub. 2 Ph CHOCH.sub.3 H H CH.sub.3 SPh SPh CHOCH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHOCH.sub.3 H H OCH.sub.3 SePh SePh CHOCH.sub.3 H H Br H SePh CHOCH.sub.3 H H OCH.sub.3 H OPh CHOCH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.3 H H OCH.sub.3 H SPh NOCH.sub.3 H H OCF.sub.2 H H SPh CHOCH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHOCH.sub.3 H H OCH.sub.3 SPh SPh NOCH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NOCH.sub.3 H H F H SPh CHOCH.sub.3 H H OCH.sub.3 SPh SPh CHOCH.sub.3 H H CF.sub.3 H SeCH.sub.3 CHOCH.sub.3 H H CF.sub.3 H SPh CHOCH.sub.3 H H OCH.sub.3 H OPh NOCH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NOCH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHOCH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHOCH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHOCH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHOCH.sub.3 6-F H OCH.sub.3 H SePh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 H SeCH.sub.3 CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 H SPh CHCH(OCH.sub.3)CH.sub.3 H H CH.sub.3 H SePh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHCH(OCH.sub.3)CH.sub.3 H H CH.sub.3 SPh SPh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 SePh SePh CHCH(OCH.sub.3)CH.sub.3 H H Br H SePh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 H OPh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 H SPh NCH(OCH.sub.3)CH.sub.3 H H OCF.sub.2 H H SPh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 SPh SPh NCH(OCH.sub.3)CH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NCH(OCH.sub.3)CH.sub.3 H H F H SPh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 SPh SPh CHCH(OCH.sub.3)CH.sub.3 H H CF.sub.3 H SeCH.sub.3 CHCH(OCH.sub.3)CH.sub.3 H H CF.sub.3 H SPh CHCH(OCH.sub.3)CH.sub.3 H H OCH.sub.3 H OPh NCH(OCH.sub.3)CH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NCH(OCH.sub.3)CH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH(OCH.sub.3)CH.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHCH(OCH.sub.3)CH.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHCH(OCH.sub.3)CH.sub.3 5-CF.sub.3 H OCH.sub.3 H SPh CHCH(OCH.sub.3)CH.sub.3 6-F H OCH.sub.3 H SePh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 H SeCH.sub.3 CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H CH.sub.3 H SePh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 H SO.sub.2 Ph CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H CH.sub. 3 SPh SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.2 CH.sub.3 H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 SePh SePh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H Br H SePh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 H OPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 H SPh NSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCF.sub.2 H H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 SPh SPh NSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H F H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 SPh SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H CF.sub.3 H SeCH.sub.3 CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H CF.sub.3 H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 H OPh NSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 3-OCH.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 5-CF.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 6-F H OCH.sub.3 H SePh CHC.sub.2 H.sub.5 H H OCH.sub.3 H SeCH.sub.3 CHCH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H SPh CHCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 H SePh CHOCH.sub.2 CH.sub.3 H H OCH.sub.3 H SO.sub.2 Ph CHOCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 SPh SPh CHF H H OCH.sub.2 CH.sub.3 H SPh CHF H H OCH.sub.3 SePh SePh CHF H H Br H SePh CHF H H OCH.sub.3 H OPh CHF H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H SPh NCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCF.sub.2 H H SPh CHCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 SPh SPh NCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 SCH.sub.3 SeCH.sub.3 NSO.sub.2 N(OCH).sub.3 CH.sub.3 H H F H SPh CHSO.sub.2 N(OCH.sub.3).sub.3 CH.sub.3 H H OCH.sub.3 SPh SPh CHOSO.sub.2 N(CH.sub.3).sub.2 H H CF.sub.3 H SeCH.sub.3 CHSOCH.sub.3 H H OCH.sub.3 H OPh NSOCH.sub.3 H H OCH.sub.2 CH.sub.3 H SeCH.sub.3 NSOCH.sub.3 H H OCH.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHSCF.sub.3 H CH.sub.3 OCH.sub.3 H SPh CHSF.sub.3 3-OCH.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2 CH.sub.2 CHCH.sub.2 5-CF.sub.3 H OCH.sub.3 H SPh CHOCH.sub.2 CHCCH 6-F H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 H H CH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CH 137-140Cl H H CH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CH 121-124CO.sub.2 C.sub.2 H.sub.5 H H CH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CHCF.sub.3 H H CH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CH 102-105SO.sub.2 CH.sub.3 H H CH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CH 176-178CO.sub.2 CH.sub.3 H H CH.sub.3 H CH.sub.2 OH CH 138-141SO.sub.2 CH.sub.3 H H CH.sub.3 H CH.sub.2 OH CH 156-158Cl H H CH.sub.3 H CH.sub.2 OH CH 124-125CF.sub.3 H H CH.sub.3 H CH.sub.2 OH CH 126-127.5CO.sub.2 CH.sub. 3 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CH 111-114CO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CHCl H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CH 169-171SO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CH 145-148CF.sub.3 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CH 139-141SO.sub.2 CH.sub.3 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CH 172-174Br H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CH 161-163NO.sub.2 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 NSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 NCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 NCH.sub.3 H H OCH.sub.3 H CH.sub.2 OH NF H H OCH.sub.3 H CH.sub.2 OH N__________________________________________________________________________ TABLE 1b______________________________________ ##STR32##R.sub.1 R.sub.2 R X.sub.1 m.p. (.degree.C.)______________________________________CO.sub.2 CH.sub.3 H H CH.sub.3 154-160CO.sub.2 CH.sub.3 H H OCH.sub.3 136.5-141CO.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 173-178SO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3CH.sub.2 CH.sub.3 H H OCH.sub.3CH.sub.2 OCH.sub.3 H H OCH.sub.3OCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3SO.sub.2 N(OCH.sub. 3)CH.sub.3 H H OCH.sub.3OSO.sub.2 CH.sub.3 H H CH.sub.3OSO.sub.2 CH.sub.3 H H OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3Ph H H OCH.sub.3 ##STR33## H H OCH.sub.3 ##STR34## H H OCH.sub.3 ##STR35## H H OCH.sub.3CO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3CO.sub.2 CH.sub.3 5-Cl H OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 6-CF.sub.3 H OCH.sub.3CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 H H OCH.sub.3CO.sub.2 CH.sub.3 H H CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3OSO.sub.2 CH.sub.3 H H OCH.sub.3CH.sub.2 CH.sub.3 H H OCH.sub.3CO.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3______________________________________ TABLE 1c______________________________________ ##STR36##R.sub.1 R.sub.2 R m.p. (.degree.C.)______________________________________H H HCO.sub.2 CH.sub.3 H HCl H H 187-194Br H HSO.sub.2 N(CH.sub.3).sub.2 H HNO.sub.2 H HCF.sub.3 H HOSO.sub.2 CH.sub.3 H HCH.sub.3 H HCO.sub.2 CH.sub.2 CH.sub.3 H HSO.sub.2 N(OCH.sub.3)CH.sub.3 H HSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H HCH.sub.2 CH.sub.3 H HCH.sub.2 OCH.sub.3 H HOCH.sub.3 H HOCH.sub.2 CHCH.sub.2 H HOCH.sub.2 C CH H HPh H HCO.sub.2 CH.sub.3 3-OCH.sub.3 HSO.sub.2 N(CH.sub.3).sub.2 5-Cl HCO.sub.2 CH.sub.3 6-CF.sub.3 HCO.sub.2 CH.sub.3 3-CH.sub.3 HCO.sub.2 CH.sub.3 H CH.sub.3______________________________________ TABLE 1d______________________________________ ##STR37##R.sub.1 R.sub.2 R m.p. (.degree.C.)______________________________________CO.sub.2 CH.sub.3 H H 153-161Cl H H 158-162Br H HSO.sub.2 N(CH.sub.3).sub.2 H H 138-142NO.sub.2 H H 180-190CF.sub.3 H HOSO.sub.2 CH.sub.3 H H 173-178CH.sub.3 H H 133-153CO.sub.2 CH.sub.2 CH.sub.3 H H 103-107SO.sub.2 N(OCH.sub.3)CH.sub.3 H HSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H HCH.sub.2 CH.sub.3 H HCH.sub.2 OCH.sub.3 H HOCH.sub.3 H HPh H HCO.sub.2 CH.sub. 3 3-OCH.sub.3 HSO.sub.2 N(CH.sub.3).sub.2 5-Cl HCO.sub.2 CH.sub.3 6-CF.sub.3 HCO.sub.2 CH.sub.3 6-CH.sub.3 HCO.sub.2 CH.sub.3 H CH.sub.3SCH.sub.3 H HSO.sub.2 CH.sub.3 H H 200-205SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H 195-200______________________________________ TABLE 1e______________________________________ ##STR38## m.p.R.sub.1 R.sub.2 R X.sub.1 E Z (.degree.C.)______________________________________OCH.sub.2 CH.sub.3 H H CH.sub.3 F CHOCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 F CHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 F CH 221-224SO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 F CH 215-220SO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 F NSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H OCH.sub.3 F CHSO.sub.2 N(OCH.sub.3)CH.sub.3 H H CH.sub.3 F CHOCH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 Cl CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 Br CHSO.sub.2 (CH.sub.3).sub.2 H H OCH.sub.3 Br N ##STR39## H H OCH.sub.3 F CHSO.sub.2 N(CH.sub.3).sub.2 3-OCH.sub.3 H OCH.sub.3 F CHSO.sub.2 N(CH.sub.3).sub.2 6-CF.sub.3 H OCH.sub.3 F CHSO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 F CHSO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 F NSO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H H CH.sub.3 F NCH.sub.2 CH.sub.3 H H OCH.sub.3 F N______________________________________ TABLE 1f__________________________________________________________________________ ##STR40##R.sub.1 R.sub.2 R X.sub.1 Z G m.p. (.degree.C.)__________________________________________________________________________CH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CH.sub.3 H H CH.sub.3 N CH(OCH.sub.3).sub.2C.sub.2 H.sub.5 H CH.sub.3 OCH.sub.3 CH CH(OCH.sub.3).sub.2C.sub.2 H.sub.5 H H OCH.sub.3 CH CH(OC.sub.2 H.sub.5).sub.2CH(CH.sub.3).sub.2 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CH(CH.sub.3)C.sub.2 H.sub.5 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OCH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OCH.sub.3 5-Cl H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OC.sub.2 H.sub.5 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OCH(CH.sub.3).sub.2 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2OC.sub.4 H.sub.9 -n H H OCH.sub.3 N CH(OCH.sub.3).sub.2OCH.sub.2 CH.sub.2 OCH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2F H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)Cl H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) 115-118Cl H H OC.sub.2 H.sub.5 CH CH(OCH.sub.2 CH.sub.2 O)Cl H H OCH.sub.3 CH CH(OCH.sub.3).sub.2Br 5-CH.sub.3 H CH.sub.3 CH CH(OCH.sub.3).sub.2NO.sub.2 H H OCH.sub.3 CH CH(OC.sub.2 H.sub.5).sub.2NO.sub.2 H CH.sub.3 CH.sub.3 CH CH(OCH.sub.3).sub.2CF.sub.3 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CO.sub.2 CH.sub. 3 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) 102-104CO.sub.2 CH.sub.3 H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) 148-150CO.sub.2 CH.sub.3 H H OC.sub.2 H.sub.5 CH CH(OCH.sub.2 CH.sub.2 O)CO.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 N CH(OCH.sub.3).sub.2CO.sub.2 C.sub.2 H.sub.5 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2CO.sub.2 CH.sub.2 CHCH.sub.2 H H CH.sub.3 CH CH(OC.sub.2 H.sub.5).sub.2CO.sub.2 C.sub.4 H.sub.9 -n H H OCH.sub.3 CH CH(OCH.sub.3).sub.2SO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) 122-124SO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) .sup. 183-185(d)SO.sub.2 N(CH.sub.3).sub.2 H H OC.sub.2 H.sub.5 CH CH(OCH.sub.3).sub.2SO.sub.2 N(CH.sub.3)C.sub.2 H.sub.5 3-CF.sub.3 H OCH.sub.3 CH CH(OCH.sub.3).sub.2OSO.sub.2 CH.sub. 3 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2OSO.sub.2 C.sub.2 H.sub.5 H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)SCF.sub.3 H H OC.sub.2 H.sub.5 CH CH(OCH.sub.3).sub.2OCHF.sub.2 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2CO.sub.2 C.sub.2 H.sub.5 H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) 151-153CO.sub.2 CH.sub.3 H H OCH.sub.3 N CH(OCH.sub.3).sub.2CO.sub.2 CH.sub.3 H H OCH.sub.3 CH CH(OC.sub.2 H.sub.5).sub.2CO.sub.2 CH.sub.3 H H CH.sub.3 CH CH(OCH.sub.3).sub.2SO.sub.2 CH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) 191-194SO.sub.2 CH.sub.3 H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) .sup. 194-196(d)SO.sub.2 CH.sub.3 H H CH.sub.3 CH CH(OCH.sub.3).sub.2SO.sub.2 CH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2SO.sub.2 C.sub.2 H.sub.5 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)SO.sub.2 CH.sub. 2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)SO.sub.2 CH.sub.2 CHCH.sub.2 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2SO.sub.2 C.sub.2 H.sub.5 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2OCH.sub.2 CCH H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OCH.sub.2 CCCH.sub.3 H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OCH.sub.2 CHCH.sub.2 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OCH.sub.2 CH.sub.2 CHCH.sub.2 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CH.sub.2 OCH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CH.sub.2 OC.sub.2 H.sub.5 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2C.sub.6 H.sub.5 6-Cl H CH.sub.3 CH CH(OC.sub.2 H.sub.5).sub.2C.sub.6 H.sub.5 6-OCH.sub.3 H OCH.sub.3 CH CH(OCH.sub.3).sub.2 ##STR41## H H OCH.sub.3 N CH(OCH.sub.2 CH.sub.2 O) ##STR42## H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) ##STR43## H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CO.sub.2 CH.sub.3 H H OCH.sub.3 CH C.sub.6 H.sub.5 110-112(d)CO.sub.2 CH.sub.3 H H CH.sub.3 CH C.sub.6 H.sub.5SO.sub.2 N(CH.sub.3).sub.2 H H OCH.sub.3 CH C.sub.6 H.sub.5SO.sub.2 CH.sub.3 H H OCH.sub.3 N C.sub.6 H.sub.5Cl H H OCH.sub.3 CH C.sub.6 H.sub.5OCHF.sub.2 H H OCH.sub.3 CH C.sub.6 H.sub.5__________________________________________________________________________ TABLE 2a__________________________________________________________________________ ##STR44##L R.sub.3 R.sub.4 R X T Y Z m.p. (.degree.C.)__________________________________________________________________________L-2 CH.sub.3 -- H OCH.sub.3 H SeCH.sub.3 CHL-2 CH.sub.3 -- H OCH.sub.3 H SePh CHL-2 OCH.sub.3 -- H CH.sub.3 H SPh CHL-2 OCH.sub.3 -- H OCH.sub.3 SPh SPh CHL-2 OCH.sub.3 -- H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-2 F -- H OCH.sub.3 H SPh NL-2 F -- H Cl H SPh CHL-2 Cl -- H OCH.sub.3 H SeCH.sub.3 CHL-2 Cl -- H OCH.sub.3 H SeCH.sub.3 NL-2 Br -- H CH.sub.3 SPh SPh NL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3 H OPh CHL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H Br H SePh CHL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3 H SePh CHL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3 H SPh NL-2 OSO.sub.2 CH.sub.3 -- H OCH.sub.3 SPh SPh NL-2 OSO.sub.2 CH.sub.3 -- H OCH.sub.3 H SO.sub.2 Ph NL-2 SOCH.sub.3 -- H F H OPh CHL-2 SOCH.sub.3 -- H OCH.sub.3 H SPh CHL-2 SCH.sub.3 -- H OCH.sub.3 H SePh CHL-2 SCH.sub.3 -- H OCH.sub.3 H SeCH.sub.3 CHL-2 SO.sub.2 CH.sub.3 -- H CH.sub.3 SeCH.sub.3 SePh CHL-2 SO.sub.2 CH.sub.3 -- H OCH.sub.3 H SPh CHL-2 SO.sub.2 CH.sub.3 -- H OCH.sub.3 H SPh NL-2 CH.sub.3 -- H OCH.sub.2 CH.sub.3 H SPh CHL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H CH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CHL-2 CH.sub.3 -- H OCH.sub.3 H SeCH.sub.3 CHL-2 OCH.sub.3 -- CH.sub.3 OCH.sub.3 H SPh CHL-3 -- CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-3 -- CH.sub.3 H OCH.sub.3 H SePh CHL-3 -- CH.sub.2 CH.sub.3 H CH.sub.3 H SPh CHL-3 -- OCH.sub.3 H OCH.sub.3 SPh SPh CHL-3 -- OCH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-3 -- F H OCH.sub.3 H SPh NL-3 -- F H Cl H SPh CHL-3 -- Cl H OCH.sub.3 H SeCH.sub.3 CHL-3 -- Cl H OCH.sub.3 H SeCH.sub.3 NL-3 -- Br H CH.sub.3 SPh SPh NL-3 -- Br H OCH.sub.3 H OPh CHL-3 -- OCH.sub.2 CH.sub.3 H Br H SePh CHL-3 -- SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SePh CHL-3 -- SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 SeCH.sub.3 SeCH.sub. 3 CHL-3 -- SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh NL-3 -- SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 SPh SPh NL-3 -- SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph NL-3 -- SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SePh CHL-3 -- SCH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-3 -- SCH.sub.3 H CH.sub.3 SeCH.sub.3 SePh CHL-3 -- SOCH.sub.3 H OCH.sub.3 H SPh CHL-3 -- SO.sub.2 CH.sub.3 H OCH.sub.3 H SPh NL-3 -- SO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 H SPh CHL-3 -- SO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-3 -- SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SPh CHL-3 -- CH.sub.3 H OCH.sub.3 H CH.sub.2 OH CH__________________________________________________________________________ TABLE 2b______________________________________ ##STR45## m.p.L R.sub.3 R.sub.4 R X.sub.1 (.degree.C.)______________________________________L-2 SO.sub.2 N(CH.sub.3).sub.2 -- H CH.sub.3L-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3L-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3L-2 CH.sub.3 -- H CH.sub.3L-2 CH.sub.3 -- H OCH.sub.3L-2 CH.sub.3 -- H OCH.sub.2 CH.sub.3L-2 H -- H OCH.sub.3L-2 H -- H OCH.sub.3L-2 F -- H OCH.sub.3L-2 Cl -- H OCH.sub.3L-2 Cl -- H CH.sub.3L-2 Br -- H OCH.sub.3L-2 OSO.sub.2 CH.sub.3 -- H OCH.sub.3L-2 OSO.sub.2 CH.sub.3 -- H CH.sub.3L-2 SCH.sub.3 -- H CH.sub.3L-2 SCH.sub.3 -- H OCH.sub.3L-2 SOCH.sub.3 -- H OCH.sub.3L-2 SOCH.sub.3 -- H OCH.sub.3L-2 SO.sub.2 CH.sub.3 -- H CH.sub.3L-2 SO.sub.2 CH.sub.3 -- H OCH.sub.3L-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.2 CH.sub.3L-2 OSO.sub.2 CH.sub.3 -- H CH.sub.3L-2 SO.sub.2 N(CH.sub.3).sub.2 -- CH.sub.3 OCH.sub.2 CH.sub.3L-2 H -- CH.sub.3 OCH.sub.3L-3 -- CH.sub.3 H CH.sub.3L-3 -- CH.sub.3 H OCH.sub.3L-3 -- CH.sub.3 H OCH.sub.3L-3 -- CH.sub.2 CH.sub.3 H OCH.sub.3L-3 -- CH.sub.2 CH.sub.3 H CH.sub.3L-3 -- OCH.sub.3 H OCH.sub.3L-3 -- OCH.sub.3 H OCH.sub.2 CH.sub.3L-3 -- F H OCH.sub.3L-3 -- F H OCH.sub.3L-3 -- Cl H OCH.sub.3L-3 -- Cl H OCH.sub.3L-3 -- Br H CH.sub.3L-3 -- Br H OCH.sub.3L-3 -- OCH.sub.2 CH.sub.3 H OCH.sub.3L-3 -- OCH.sub.2 CH.sub.3 H CH.sub.3L-3 -- SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3L-3 -- SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3L-3 -- SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3L-3 -- SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3L-3 -- SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3L-3 -- SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3L-3 -- SCH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3L-3 -- SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3______________________________________ TABLE 2c______________________________________ ##STR46##L R.sub.3 R.sub.4 R m.p. (.degree.C.)______________________________________L-2 H -- HL-2 CH.sub.3 -- HL-2 OCH.sub.3 -- HL-2 F -- HL-2 Cl -- HL-2 Br -- HL-2 SO.sub.2 N(CH.sub.3).sub.2 -- HL-2 OSO.sub.2 CH.sub.3 -- HL-2 SCH.sub.3 -- HL-2 SOCH.sub.3 -- HL-2 SO.sub.2 CH.sub.3 -- HL-2 CH.sub.3 -- CH.sub.3L-3 -- CH.sub.3 HL-3 -- CH.sub.2 CH.sub.3 HL-3 -- OCH.sub.3 HL-3 -- OCH.sub.2 CH.sub.3 HL-3 -- F HL-3 -- Cl HL-3 -- Br HL-3 -- SO.sub.2 N(CH.sub.3).sub.2 HL-3 -- SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 HL-3 -- SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-3 -- SCH.sub.3 HL-3 -- SO.sub.2 CH.sub.3 HL-3 -- CH.sub.3 CH.sub.3______________________________________ TABLE 2d______________________________________ ##STR47##L R.sub.3 R.sub.4 R m.p. (.degree.C.)______________________________________L-2 H -- HL-2 CH.sub.3 -- HL-2 OCH.sub.3 -- HL-2 F -- HL-2 Cl -- HL-2 Br -- HL-2 SO.sub.2 N(CH.sub.3).sub.2 -- HL-2 OSO.sub.2 CH.sub.3 -- HL-2 SCH.sub.3 -- HL-2 SOCH.sub.3 -- HL-2 SO.sub.2 CH.sub.3 -- HL-2 CH.sub.3 -- CH.sub.3L-3 -- CH.sub.3 HL-3 -- CH.sub.2 CH.sub.3 HL-3 -- OCH.sub.3 HL-3 -- OCH.sub.2 CH.sub.3 HL-3 -- F HL-3 -- Cl HL-3 -- Br HL-3 -- SO.sub.2 N(CH.sub.3).sub.2 HL-3 -- SO.sub.2 N(CH.sub.2 CH.sub. 3).sub.2 HL-3 -- SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-3 -- SCH.sub.3 HL-3 -- SO.sub.2 CH.sub.3 HL-3 -- CH.sub.3 CH.sub.3______________________________________ TABLE 2e______________________________________ ##STR48## m.p.L R.sub.3 R.sub.4 R X.sub.1 E Z (.degree.C.)______________________________________L-2 H -- H OCH.sub.3 F CHL-2 CH.sub.3 -- H OCH.sub.3 F CHL-2 CH.sub.3 -- H OCH.sub.3 Cl CHL-2 OCH.sub.3 -- H CH.sub.3 F CHL-2 F -- H OCH.sub.3 F CHL-2 Cl -- H OCH.sub.3 F CHL-2 Cl -- H OCH.sub.3 Cl CHL-2 Br -- H CH.sub.3 F NL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3 F CHL-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3 Br CHL-2 OSO.sub.2 CH.sub.3 -- H OCH.sub.3 F CHL-3 -- CH.sub.2 CH.sub.3 H OCH.sub.3 F CHL-3 -- OCH.sub.3 H OCH.sub.3 F NL-3 -- F H CH.sub.3 F CHL-3 -- Br H OCH.sub.3 Br CHL-3 -- SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 F CHL-3 -- SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 F NL-3 -- SCH.sub.3 H CH.sub.3 Cl CHL-3 -- SO.sub.2 CH.sub.3 H OCH.sub.3 F CHL-3 -- CH.sub.3 CH.sub.3 OCH.sub.3 F CHL-3 -- OCH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 Br N______________________________________ TABLE 2f__________________________________________________________________________ ##STR49##L R.sub.3 R.sub.4 R X Z G m.p. (.degree.C.)__________________________________________________________________________L-2 Cl -- H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-2 Cl -- H CH.sub.3 CH CH(OCH.sub.3).sub.2L-2 OCH.sub.3 -- H OCH.sub.3 CH CH(OCH.sub.3).sub.2L-2 OCH.sub.3 -- H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-2 OSO.sub.2 CH.sub.3 -- H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-2 SO.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH CH(OCH.sub.3).sub.2L-2 SCH.sub.3 -- H OCH.sub.3 N CH(OCH.sub.2 CH.sub.2 O)L-2 Br -- H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-2 SO.sub.2 N(CH.sub.3).sub.2 -- H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-2 CH.sub.3 -- H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-3 -- CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-3 -- OCH.sub.3 H OCH.sub.3 CH CH(OCH.sub.3).sub.2L-3 -- OC.sub.2 H.sub.5 H CH.sub.3 N CH(OC.sub.2 H.sub.5).sub.2L-3 -- Cl H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-3 -- SO.sub.2 C.sub.2 H.sub.5 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-3 -- SO.sub.2 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-2 Cl -- H OCH.sub.3 CH C.sub.6 H.sub.5L-2 OCH.sub.3 -- H OCH.sub.3 N C.sub.6 H.sub.5L-3 -- SO.sub.2 CH.sub.3 H CH.sub.3 CH C.sub.6 H.sub.5L-3 -- Cl H OCH.sub.3 CH C.sub.6 H.sub.5__________________________________________________________________________ TABLE 3a__________________________________________________________________________ ##STR50##L R.sub.5 R X T Y Z m.p. (.degree.C.)__________________________________________________________________________L-4 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-4 CH.sub.3 H OCH.sub.3 H SePh CHL-4 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-4 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SOPh CHL-4 F H OCH.sub.3 H SO.sub.2 Ph CHL-4 Cl H CH.sub.3 H SeCH.sub.3 CHL-4 Cl H CH.sub.3 H SePh CHL-4 Br H CH.sub.3 H SPh CHL-4 Br H CH.sub.3 H SO.sub.2 Ph CHL-4 NO.sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-4 NO.sub.2 H OCH.sub.3 H SPh CHL-4 NO.sub.2 H OCH.sub.3 H SePh CHL-4 NO.sub.2 H OCH.sub. 3 H SO.sub.2 Ph CHL-4 NO.sub.2 H CH.sub.3 H SeCH.sub.3 CHL-4 NO.sub.2 H CH.sub.3 H SPh CHL-4 NO.sub.2 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-4 NO.sub.2 H OCH.sub.3 H OPh CHL-4 NO.sub.2 H OCH.sub.3 H SeCH.sub.3 NL-4 NO.sub.2 H OCH.sub.3 H SPh NL-4 NO.sub.2 H CH.sub.3 SePh SePh NL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SOPh CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H OPh CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SePh CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SPh NL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SePh NL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 NL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph NL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 SePh SePh NL-4 CO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh NL-4 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SePh CHL-4 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SPH CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SePh CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SPh CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SOPh CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SO.sub.2 Ph CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SePh CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SPh CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 SPh SO.sub.2 Ph CHL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 NL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SePh NL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H SO.sub.2 Ph NL-4 CO.sub.2 CH.sub.3 H CH.sub.3 H OPh CHL-4 CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 H SPh CHL-4 CO.sub.2 CH.sub.3 H F H SPh CHL-4 CO.sub.2 CH.sub.3 H Cl H SPh CHL-4 CO.sub.2 CH.sub.3 H CF.sub.3 H SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.3 H CF.sub.3 H SePh CHL-4 CO.sub.2 CH.sub.3 H OCHF.sub.2 H SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.3 H OCHF.sub.2 H SPh CHL-4 CO.sub.2 CH.sub.3 H Br H SPh CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHL-4 CO.sub.2 CH.sub. 2 CH.sub.3 H CH.sub.3 H SPh NL-4 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-4 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SePh CHL-4 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SPh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SePh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh NL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SePh SePh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SPh SPh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H OPh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SePh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SPh CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SO.sub.2 Ph CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 NL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 SPh SPh CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SePh CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SPh CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 NL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SePh NL-4 SO.sub.2 N(CH.sub.2 CH.sub.3 ).sub.2 H OCH.sub.3 H SPh NL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 NL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SPh CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SePh CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SPh CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H CH.sub.3 H SePh CHL-4 SCH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-4 SCH.sub.3 H OCH.sub.3 H SePh CHL-4 SCH.sub.3 H OCH.sub.3 H SPh CHL-4 SOCH.sub.3 H OCH.sub.3 H SePh CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 H SePh NL-5 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-5 CH.sub.3 H OCH.sub.3 H SePh CHL-5 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-5 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SOPh CHL-5 F H OCH.sub.3 H SO.sub.2 Ph CHL-5 Cl H CH.sub.3 H SeCH.sub.3 CHL-5 Cl H CH.sub.3 H SePh CHL-5 Br H CH.sub.3 H SPh CHL-5 Br H CH.sub.3 H SO.sub.2 Ph CHL-5 NO.sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-5 NO.sub.2 H OCH.sub.3 H SPh CHL-5 NO.sub.2 H OCH.sub.3 H SePh CHL-5 NO.sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-5 NO.sub.2 H CH.sub.3 H SeCH.sub.3 CHL-5 NO.sub.2 H CH.sub.3 H SPh CHL-5 NO.sub.2 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-5 NO.sub.2 H OCH.sub.3 H OPh CHL-5 NO.sub.2 H OCH.sub.3 H SeCH.sub.3 NL-5 NO.sub.2 H OCH.sub.3 H SPh NL-5 NO.sub.2 H CH.sub.3 SePh SePh NL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SOPh CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H OPh CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SePh CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SPh NL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SePh NL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 NL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph NL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 SePh SePh NL-5 CO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh NL-5 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SePh CHL-5 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SPh CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SePh CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SPh CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SOPh CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SO.sub.2 Ph CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SePh CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SPh CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 SPh SO.sub.2 Ph CHL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 NL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SePh NL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H SO.sub.2 Ph NL-5 CO.sub.2 CH.sub.3 H CH.sub.3 H OPh CHL-5 CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 H SPh CHL-5 CO.sub.2 CH.sub.3 H F H SPh CHL-5 CO.sub.2 CH.sub.3 H Cl H SPh CHL-5 CO.sub.2 CH.sub.3 H CF.sub.3 H SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.3 H CF.sub.3 H SePh CHL-5 CO.sub.2 CH.sub.3 H OCHF.sub.2 H SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.3 H OCHF.sub.2 H SPh CHL-5 CO.sub.2 CH.sub.3 H Br H SPh CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SPh NL-5 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-5 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SePh CHL-5 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SPh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SePh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh NL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SePh SePh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SPh SPh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H OPh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SePh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SPh CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SO.sub.2 Ph CHL-5 SO.sub.2 N(CH.sub. 3).sub.2 H CH.sub.3 H SeCH.sub.3 NL-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 SPh SPh CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SePh CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SPh CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 NL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SePh NL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SPh NL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 NL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SPh CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub. 3 H OCH.sub.3 H SeCH.sub.3 CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SePh CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SPh CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H CH.sub.3 H SePh CHL-5 SCH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-5 SCH.sub.3 H OCH.sub.3 H SePh CHL-5 SCH.sub.3 H OCH.sub.3 H SPh CHL-5 SOCH.sub.3 H OCH.sub.3 H SePh CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 H SePh NL-6 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-6 CH.sub.3 H OCH.sub.3 H SePh CHL-6 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-6 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SOPh CHL-6 F H OCH.sub.3 H SO.sub.2 Ph CHL-6 Cl H CH.sub.3 H SeCH.sub.3 CHL-6 Cl H CH.sub.3 H SePh CHL-6 Br H CH.sub.3 H SPh CHL-6 Br H CH.sub.3 H SO.sub.2 Ph CHL-6 NO.sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-6 NO.sub.2 H OCH.sub.3 H SPh CHL-6 NO.sub.2 H OCH.sub.3 H SePh CHL-6 NO.sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-6 NO.sub.2 H CH.sub.3 H SeCH.sub.3 CHL-6 NO.sub.2 H CH.sub.3 H SPh CHL-6 NO.sub.2 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-6 NO.sub.2 H OCH.sub.3 H OPh CHL-6 NO.sub.2 H OCH.sub.3 H SeCH.sub.3 NL-6 NO.sub.2 H OCH.sub.3 H SPh NL-6 NO.sub.2 H CH.sub.3 SePh SePh NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SOPh CHL-6 CO.sub.2 CH.sub. 3 H OCH.sub.3 H SO.sub.2 Ph CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H OPh CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SePh CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SPh NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SePh NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 SePh SePh NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh NL-6 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SePh CHL-6 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SPh CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H SePh CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H SPh CHL-6 CO.sub.2 CH.sub. 3 H CH.sub.3 H SOPh CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H SO.sub.2 Ph CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SePh CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 SeCH.sub.3 SPh CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 SPh SO.sub.2 Ph CHL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 NL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H SePh NL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H SO.sub.2 Ph NL-6 CO.sub.2 CH.sub.3 H CH.sub.3 H OPh CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 H SPh CHL-6 CO.sub.2 CH.sub.3 H F H SPh CHL-6 CO.sub.2 CH.sub.3 H Cl H SPh CHL-6 CO.sub.2 CH.sub.3 H CF.sub.3 H SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.3 H CF.sub.3 H SePh CHL-6 CO.sub.2 CH.sub.3 H OCHF.sub.2 H SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.3 H OCHF.sub.2 H SPh CHL-6 CO.sub.2 CH.sub. 3 H Br H SPh CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SPh NL-6 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-6 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SePh CHL-6 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SPH CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SePh CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh CHL-6 SO.sub. 2 N(CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh NL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SePh SePh CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SPh SPh CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H OPh CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SePh CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SPh CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SO.sub.2 Ph CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 NL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 SPh SPh CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3 ).sub.2 H OCH.sub.3 H SePh CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SPh CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 NL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SePh NL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 H SPh NL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 NL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 H SPh CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SePh CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SPh CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H CH.sub.3 H SePh CHL-6 SCH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-6 SCH.sub.3 H OCH.sub.3 H SePh CHL-6 SCH.sub.3 H OCH.sub.3 H SPh CHL-6 SOCH.sub.3 H OCH.sub.3 H SePh CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 H SePh NL-4 CH.sub.3 H OCH.sub.3 H CH.sub.2 OH CHL-5 Br H OCH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 CHL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H CH.sub.2 OH NL-6 CO.sub.2 CH.sub.3 H OCH.sub.3 H OSi(CH.sub.3).sub.3 N__________________________________________________________________________ TABLE 3b______________________________________ ##STR51##L R.sub.5 R X.sub.1 m.p. (.degree.C.)______________________________________L-4 CH.sub.3 H CH.sub.3L-4 CH.sub.3 H OCH.sub.3L-4 CH.sub.2 CH.sub.3 H CH.sub.3L-4 CH.sub.2 CH.sub.3 H OCH.sub.3L-4 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3L-4 F H OCH.sub.3L-4 Cl H OCH.sub.3L-4 Cl H CH.sub.3L-4 Br H OCH.sub.3L-4 NO.sub.2 H CH.sub.3L-4 NO.sub.2 H OCH.sub.3L-4 NO.sub.2 H OCH.sub.2 CH.sub.3L-4 CO.sub.2 CH.sub.3 H OCH.sub.3L-4 CO.sub.2 CH.sub.3 H CH.sub.3L-4 CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3L-4 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3L-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3L-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3L-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.2 CH.sub.3L-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3L-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3L-4 SCH.sub.3 H OCH.sub.3L-4 SOCH.sub.3 H OCH.sub.3L-4 SO.sub.2 CH.sub.3 H CH.sub.3L-4 SO.sub.2 CH.sub.3 H OCH.sub.3L-4 SO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3L-5 CH.sub.3 H CH.sub.3L-5 CH.sub.3 H OCH.sub.3L-5 CH.sub.2 CH.sub.3 H CH.sub.3L-5 CH.sub.2 CH.sub.3 H OCH.sub.3L-5 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3L-5 F H OCH.sub.3L-5 Cl H OCH.sub.3L-5 Cl H CH.sub.3L-5 Br H OCH.sub.3L-5 NO.sub.2 H CH.sub.3L-5 NO.sub.2 H OCH.sub.3L-5 NO.sub.2 H OCH.sub.2 CH.sub.3L-5 CO.sub.2 CH.sub.3 H OCH.sub.3L-5 CO.sub.2 CH.sub.3 H CH.sub.3L-5 CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3L-5 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3L-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3L-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3L-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.2 CH.sub.3L-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3L-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3L-5 SCH.sub.3 H OCH.sub.3L-5 SOCH.sub.3 H OCH.sub.3L-5 SO.sub.2 CH.sub.3 H CH.sub.3L-5 SO.sub.2 CH.sub.3 H OCH.sub.3L-5 SO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3L-6 CH.sub.3 H CH.sub.3L-6 CH.sub.3 H OCH.sub.3L-6 CH.sub.2 CH.sub.3 H CH.sub.3L-6 CH.sub.2 CH.sub.3 H OCH.sub.3L-6 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3L-6 F H OCH.sub.3L-6 Cl H OCH.sub.3L-6 Cl H CH.sub.3L-6 Br H OCH.sub.3L-6 NO.sub.2 H CH.sub.3L-6 NO.sub.2 H OCH.sub.3L-6 NO.sub.2 H OCH.sub.2 CH.sub.3L-6 CO.sub.2 CH.sub.3 H OCH.sub.3L-6 CO.sub.2 CH.sub.3 H CH.sub.3L-6 CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3L-6 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3L-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3L-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3L-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.2 CH.sub.3L-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3L-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3L-6 SCH.sub.3 H OCH.sub.3L-6 SOCH.sub.3 H OCH.sub.3L-6 SO.sub.2 CH.sub.3 H CH.sub.3L-6 SO.sub.2 CH.sub.3 H OCH.sub.3L-6 SO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3______________________________________ TABLE 3c______________________________________ ##STR52##L R.sub.5 R m.p. (.degree.C.)______________________________________L-4 CH.sub.3 HL-4 CH.sub.2 CH.sub.3 HL-4 CH.sub.2 CH.sub.2 CH.sub.3 HL-4 F HL-4 Cl HL-4 Br HL-4 NO.sub.2 HL-4 CO.sub.2 CH.sub.3 HL-4 CO.sub.2 CH.sub.2 CH.sub.3 HL-4 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 HL-4 SO.sub.2 N(CH.sub.3).sub.2 HL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 HL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-4 SCH.sub.3 HL-4 SOCH.sub.3 HL-4 SO.sub.2 CH.sub.3 HL-4 CO.sub.2 CH.sub.3 CH.sub.3L-5 CH.sub.3 HL-5 CH.sub.2 CH.sub.3 HL-5 CH.sub.2 CH.sub.2 CH.sub.3 HL-5 F HL-5 Cl HL-5 Br HL-5 NO.sub.2 HL-5 CO.sub.2 CH.sub.3 HL-5 CO.sub. 2 CH.sub.2 CH.sub.3 HL-5 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 HL-5 SO.sub.2 N(CH.sub.3).sub.2 HL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 HL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-5 SCH.sub.3 HL-5 SOCH.sub.3 HL-5 SO.sub.2 CH.sub.3 HL-5 CO.sub.2 CH.sub.3 CH.sub.3L-6 CH.sub.3 HL-6 CH.sub.2 CH.sub.3 HL-6 CH.sub.2 CH.sub.2 CH.sub.3 HL-6 F HL-6 Cl HL-6 Br HL-6 NO.sub.2 HL-6 CO.sub.2 CH.sub.3 HL-6 CO.sub.2 CH.sub.2 CH.sub.3 HL-6 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 HL-6 SO.sub.2 N(CH.sub.3).sub.2 HL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 HL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-6 SCH.sub.3 HL-6 SOCH.sub.3 HL-6 SO.sub.2 CH.sub.3 HL-6 CO.sub.2 CH.sub.3 CH.sub.3______________________________________ TABLE 3d______________________________________ ##STR53##L R.sub.5 R m.p. (.degree.C.)______________________________________L-4 CH.sub.3 HL-4 CH.sub.2 CH.sub.3 HL-4 CH.sub.2 CH.sub.2 CH.sub.3 HL-4 F HL-4 Cl HL-4 Br HL-4 NO.sub.2 HL-4 CO.sub.2 CH.sub.3 HL-4 CO.sub.2 CH.sub.2 CH.sub.3 HL-4 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 HL-4 SO.sub.2 N(CH.sub.3).sub.2 HL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 HL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-4 SCH.sub.3 HL-4 SOCH.sub.3 HL-4 SO.sub.2 CH.sub.3 HL-4 CO.sub.2 CH.sub.3 CH.sub.3L-5 CH.sub.3 HL-5 CH.sub.2 CH.sub.3 HL-5 CH.sub.2 CH.sub.2 CH.sub.3 HL-5 F HL-5 Cl HL-5 Br HL-5 NO.sub.2 HL-5 CO.sub.2 CH.sub.3 HL-5 CO.sub.2 CH.sub.2 CH.sub.3 HL-5 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 HL-5 SO.sub.2 N(CH.sub.3).sub.2 HL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 HL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-5 SCH.sub.3 HL-5 SOCH.sub.3 HL-5 SO.sub.2 CH.sub.3 HL-5 CO.sub.2 CH.sub.3 CH.sub.3L-6 CH.sub.3 HL-6 CH.sub.2 CH.sub.3 HL-6 CH.sub.2 CH.sub.2 CH.sub.3 HL-6 F HL-6 Cl HL-6 Br HL-6 NO.sub.2 HL-6 CO.sub.2 CH.sub.3 HL-6 CO.sub.2 CH.sub.2 CH.sub.3 HL-6 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 HL-6 SO.sub.2 N(CH.sub.3).sub.2 HL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 HL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 HL-6 SCH.sub.3 HL-6 SOCH.sub.3 HL-6 SO.sub.2 CH.sub.3 HL-6 CO.sub.2 CH.sub.3 CH.sub.3______________________________________ TABLE 3e______________________________________ ##STR54## m.p.L R.sub.5 R X.sub.1 E Z (.degree.C.)______________________________________L-4 CH.sub.3 H OCH.sub.3 F CHL-4 CH.sub.3 H OCH.sub.3 Cl CHL-4 CH.sub.3 H OCH.sub.3 F NL-4 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHL-4 CH.sub.2 CH.sub.3 H OCH.sub.3 Cl CHL-4 CH.sub.2 CH.sub.3 H OCH.sub.3 Br CHL-4 CH.sub.2 CH.sub.3 H OCH.sub.3 F NL-4 CH.sub.2 CH.sub.3 H CH.sub.3 F CHL-4 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHL-4 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 F CHL-4 F H OCH.sub.3 F CHL-4 F H OCH.sub.3 Cl CHL-4 Cl H OCH.sub.3 F CHL-4 Cl H CH.sub.3 F CHL-4 Cl H OCH.sub.3 F NL-4 NO.sub.2 H OCH.sub.3 F CHL-4 NO.sub.2 H OCH.sub.3 Cl CHL-4 NO.sub.2 H OCH.sub.3 F NL-4 NO.sub.2 H CH.sub.3 Br CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 F CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 Cl CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 Br CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 F NL-4 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 F CHL-4 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.2 CH.sub.3 F CHL-4 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 F CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 F CHL-4 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 F NL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 F CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 Cl CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 Br CHL-4 SO.sub.2 N(OCH.sub.3)CH.sub.3 H CH.sub.3 F CHL-4 SCH.sub.3 H OCH.sub.3 F CHL-4 SCH.sub.3 H OCH.sub.3 Cl CHL-4 SCH.sub.3 H OCH.sub.3 Br CHL-4 SCH.sub.3 H CH.sub.3 F CHL-4 SOCH.sub.3 H OCH.sub.3 F CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 F CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 Cl CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 Br CHL-4 SO.sub.2 CH.sub.3 H OCH.sub.3 F NL-4 SO.sub.2 CH.sub.3 H CH.sub.3 F CHL-4 SO.sub.2 CH.sub.3 H CH.sub.3 Cl CHL-5 CH.sub.3 H OCH.sub.3 F CHL-5 CH.sub.3 H OCH.sub.3 Cl CHL-5 CH.sub.3 H OCH.sub.3 F NL-5 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHL-5 CH.sub.2 CH.sub.3 H OCH.sub.3 Cl CHL-5 CH.sub.2 CH.sub.3 H OCH.sub.3 Br CHL-5 CH.sub.2 CH.sub.3 H OCH.sub.3 F NL-5 CH.sub.2 CH.sub.3 H CH.sub.3 F CHL-5 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHL-5 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 F CHL-5 F H OCH.sub.3 F CHL-5 F H OCH.sub.3 Cl CHL-5 Cl H OCH.sub.3 F CHL-5 Cl H CH.sub.3 F CHL-5 Cl H OCH.sub.3 F NL-5 NO.sub.2 H OCH.sub.3 F CHL-5 NO.sub.2 H OCH.sub.3 Cl CHL-5 NO.sub.2 H OCH.sub.3 F NL-5 NO.sub.2 H CH.sub.3 Br CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 F CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 Cl CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 Br CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 F NL-5 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 F CHL-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.2 CH.sub.3 F CHL-5 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 F CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 F CHL-5 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 F NL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 F CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 Cl CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 Br CHL-5 SO.sub.2 N(OCH.sub.3)CH.sub.3 H CH.sub.3 F CHL-5 SCH.sub.3 H OCH.sub.3 F CHL-5 SCH.sub.3 H OCH.sub.3 Cl CHL-5 SCH.sub.3 H OCH.sub.3 Br CHL-5 SCH.sub.3 H CH.sub.3 F CHL-5 SOCH.sub.3 H OCH.sub.3 F CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 F CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 Cl CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 Br CHL-5 SO.sub.2 CH.sub.3 H OCH.sub.3 F NL-5 SO.sub.2 CH.sub.3 H CH.sub.3 F CHL-5 SO.sub.2 CH.sub.3 H CH.sub.3 Cl CHL-6 CH.sub.3 H OCH.sub.3 F CHL-6 CH.sub.3 H OCH.sub.3 Cl CHL-6 CH.sub.3 H OCH.sub.3 F NL-6 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHL-6 CH.sub.2 CH.sub.3 H OCH.sub.3 Cl CHL-6 CH.sub.2 CH.sub.3 H OCH.sub.3 Br CHL-6 CH.sub.2 CH.sub.3 H OCH.sub.3 F NL-6 CH.sub.2 CH.sub.3 H CH.sub.3 F CHL-6 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHL-6 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 F CHL-6 F H OCH.sub.3 F CHL-6 F H OCH.sub.3 Cl CHL-6 Cl H OCH.sub.3 F CHL-6 Cl H CH.sub.3 F CHL-6 Cl H OCH.sub.3 F NL-6 NO.sub.2 H OCH.sub.3 F CHL-6 NO.sub.2 H OCH.sub.3 Cl CHL-6 NO.sub.2 H OCH.sub.3 F NL-6 NO.sub.2 H CH.sub.3 Br CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 F CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 Cl CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 Br CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 F NL-6 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 F CHL-6 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.2 CH.sub.3 F CHL-6 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 F CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub. 3 F CHL-6 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 F NL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 F CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 Cl CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H OCH.sub.3 Br CHL-6 SO.sub.2 N(OCH.sub.3)CH.sub.3 H CH.sub.3 F CHL-6 SCH.sub.3 H OCH.sub.3 F CHL-6 SCH.sub.3 H OCH.sub.3 Cl CHL-6 SCH.sub.3 H OCH.sub.3 Br CHL-6 SCH.sub.3 H CH.sub.3 F CHL-6 SOCH.sub.3 H OCH.sub.3 F CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 F CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 Cl CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 Br CHL-6 SO.sub.2 CH.sub.3 H OCH.sub.3 F NL-6 SO.sub.2 CH.sub.3 H CH.sub.3 F CHL-6 SO.sub.2 CH.sub.3 H CH.sub.3 Cl CH______________________________________ TABLE 3f__________________________________________________________________________ ##STR55##L R.sub.5 R X Z G m.p. (.degree.C.)__________________________________________________________________________L-4 CO.sub.2 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-4 CH.sub.3 H OCH.sub.3 N CH(OCH.sub.3).sub.2L-4 Br H OCH.sub.3 CH CH(OCH.sub.3).sub.2L-4 CO.sub.2 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.3).sub.2L-5 CO.sub.2 CH.sub.3 H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O) 146-148L-5 CO.sub.2 CH.sub.3 H OCH.sub.3 CH C.sub.6 H.sub.5L-5 SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH CH(OCH.sub.3).sub.2L-5 CH.sub.3 H OCH.sub.3 N CH(OCH.sub.3).sub.2L-5 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 CH CH(OCH.sub.3).sub.2L-5 Cl H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-6 CO.sub.2 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-6 CO.sub.2 CH.sub.3 H OCH.sub.3 CH C.sub.6 H.sub.5L-6 SCH.sub.3 H CH.sub.3 CH CH(OCH.sub.3).sub.2__________________________________________________________________________ TABLE 4a______________________________________ ##STR56## m.p.R.sub.6 R X Y T Z (.degree.C.)______________________________________Cl H OCH.sub.3 H SPh CHNO.sub.2 H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHCO.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H OCH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H OCH.sub.3 H OPh CHCO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 NCO.sub.2 CH.sub.3 H OCH.sub.3 H SePh NCO.sub.2 CH.sub.3 H OCH.sub.3 H SPh NCO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SeCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SePh CHSO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SO.sub.2 Ph CHSO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H OPh CHSO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 H SPh NSO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHSO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh NOCH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHOCH.sub.3 H OCH.sub.3 H SePh CHOCH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHSO.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHSO.sub.2 CH.sub.3 H OCH.sub.3 H SePh CHSO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SPh CHSO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H SO.sub.2 Ph CHCl CH.sub.3 CH.sub.3 H SPh CHNO.sub.2 H CH.sub.3 H SPh CHCO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHCO.sub.2 CH.sub.3 H CH.sub.3 H SePh CHCO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHCO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H CH.sub.3 H OPh CHCO.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 NCO.sub.2 CH.sub.3 H OCH.sub.3 SePh SePh NCO.sub.2 CH.sub.3 H CH.sub.3 H SPh NCO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SeCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 H SePh CHSO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 H SPh CHSO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 SPh SO.sub.2 Ph CHSO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H OPh CHSO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 H SPh NSO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H SPh CHSO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh NOCH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 H CH.sub.3 H SePh CHCH.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHSO.sub.2 CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHSO.sub.2 CH.sub.3 H OCH.sub.3 SePh SePh CHSO.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh CHSO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 H SO.sub.2 Ph CHCO.sub.2 CH.sub.3 H OCH.sub.3 H OSi(CH.sub.3).sub.3 CHSO.sub.2 CH.sub.3 H CH.sub.3 H CH.sub.2 OH N______________________________________ TABLE 4b______________________________________ ##STR57##R.sub.6 R X.sub.1 m.p. (.degree.C.)______________________________________Cl H OCH.sub.3NO.sub.2 H OCH.sub.3CO.sub.2 CH.sub.3 H CH.sub.3CO.sub.2 CH.sub.3 H OCH.sub.3CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3OSO.sub.2 CH.sub.3 H OCH.sub.3SO.sub.2 CH.sub.3 H OCH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3OCH.sub.3 CH.sub.3 OCH.sub.3OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3______________________________________ TABLE 4c______________________________________ ##STR58##R.sub.6 R m.p. (.degree.C.)______________________________________Cl HNO.sub.2 HCO.sub.2 CH.sub.3 HCO.sub.2 CH.sub.2 CH.sub.3 HSO.sub.2 N(CH.sub.3).sub.2 HOSO.sub.2 CH.sub.3 HSO.sub.2 CH.sub.3 HSO.sub.2 CH.sub.2 CH.sub.3 HOCH.sub.3 CH.sub.3OCH.sub.2 CH.sub.3 CH.sub.3______________________________________ TABLE 4d______________________________________ ##STR59##R.sub.6 R m.p. (.degree.C.)______________________________________Cl HNO.sub.2 HCO.sub.2 CH.sub.3 HCO.sub.2 CH.sub.2 CH.sub.3 HSO.sub.2 N(CH.sub.3).sub.2 HOSO.sub.2 CH.sub.3 HSO.sub.2 CH.sub.3 HSO.sub.2 CH.sub.2 CH.sub.3 HOCH.sub.3 HOCH.sub.2 CH.sub.3 CH.sub.3______________________________________ TABLE 4e______________________________________ ##STR60##R.sub.6 R X.sub.1 E Z m.p. (.degree.C.)______________________________________Cl H OCH.sub.3 F CHNO.sub.2 H CH.sub.3 F CHNO.sub.2 H OCH.sub.3 F CHNO.sub.2 H OCH.sub.3 Cl CHCO.sub.2 CH.sub.3 H OCH.sub.3 F CHCO.sub.2 CH.sub.3 H CH.sub.3 Cl CHCO.sub.2 CH.sub.3 H OCH.sub.3 Br CHCO.sub.2 CH.sub.3 H OCH.sub.3 F NCO.sub.2 CH.sub.3 H CH.sub.3 F CHCO.sub.3 CH.sub.3 H OCH.sub.2 CH.sub.3 F CHCO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHSO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 F CHSO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub. 3 F NSO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 Cl CHSO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 Br CHOSO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 F CHSO.sub.2 CH.sub.3 H OCH.sub.3 F CHSO.sub.2 CH.sub.3 H CH.sub.3 F CHSO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 F CHOCH.sub.3 H OCH.sub.3 F CHOCH.sub.2 CH.sub.3 H OCH.sub.3 F CHOCH.sub.2 CH.sub.3 H OCH.sub.3 Br CHOCH.sub.2 CH.sub.3 H OCH.sub.3 F N______________________________________ TABLE 4f______________________________________ ##STR61## m.p.R.sub.6 R X Z G (.degree.C.)______________________________________Cl H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)NO.sub.2 H OCH.sub.3 N CH(OCH.sub.2 CH.sub.2 O)CO.sub.2 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CO.sub.2 CH.sub.3 H CH.sub.3 CH CH(OCH.sub.3).sub.2SO.sub.2 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)OCH.sub.3 H OCH.sub.3 CH C.sub.6 H.sub.5OSO.sub.2 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)______________________________________ TABLE 5a__________________________________________________________________________ ##STR62##R.sub.7 R.sub.8 R.sub.9 R Q.sub.1 X T Y Z m m.p. (.degree.C.)__________________________________________________________________________CH.sub.3 H H H O OCH.sub.3 H SeCH.sub.3 CH 0CH.sub.3 H H H O OCH.sub.3 H SePh CH 0CH.sub. 3 H H H O OCH.sub.3 H SPh CH 0CH.sub.3 H H H O OCH.sub.3 H SO.sub.2 Ph CH 0CH.sub.3 H H H O OCH.sub.3 H SPh N 0CH.sub.3 H H H O OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.3 H H H O CH.sub.3 H SeCH.sub.3 CH 0CH.sub.3 H H H O CH.sub.3 H SePh CH 0CH.sub.3 CH.sub.3 H H O CH.sub.3 H SPh CH 0CH.sub.3 H H CH.sub.3 O CH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.3 H H H O CH.sub.3 SeCH.sub.3 SPh CH 0CH.sub.3 H H H O CH.sub.3 SPh SPh CH 0CH.sub.3 H H H O CH.sub.3 H OPh CH 0CH.sub.3 H H H O OCH.sub.3 H OPh CH 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SeCH.sub.3 CH 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SePh CH 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SPh CH 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SO.sub.2 Ph CH 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SPh N 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SeCH.sub.3 N 0CH.sub.2 CH.sub.3 H H H O CH.sub.3 H SeCH.sub.3 CH 0CH.sub. 2 CH.sub.3 H H H O CH.sub.3 H SePh CH 0CH.sub.2 CH.sub.3 H H H O CH.sub.3 H SPh CH 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.2 CH.sub.3 H H H O OCH.sub.3 SPh SPh CH 0CH.sub.3 H CH.sub.3 H O OCH.sub.3 H SePh CH 0CH.sub.3 H CH.sub.3 H O OCH.sub.3 H SPh CH 0CH.sub.3 H H H O OCH.sub.3 H SeCH.sub.3 CH 1CH.sub.3 H H H O OCH.sub.3 H SePh CH 1CH.sub.3 H H H O OCH.sub.3 H SPh CH 1CH.sub.3 H H H O OCH.sub.3 H SO.sub.2 Ph CH 1CH.sub.3 H H H O OCH.sub.3 H SPh N 1CH.sub.3 H H H O OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 1CH.sub.3 H H H O CH.sub.3 H SeCH.sub.3 CH 1CH.sub.3 H H H O CH.sub.3 H SePh CH 1CH.sub.3 CH.sub.3 H H O CH.sub.3 H SPh CH 1CH.sub.3 H H CH.sub.3 O CH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 1CH.sub.3 H H H O CH.sub.3 SeCH.sub.3 SPh CH 1CH.sub.3 H H H O CH.sub.3 SPh SPh CH 1CH.sub.3 H H H O CH.sub.3 H OPh CH 1CH.sub.3 H H H O OCH.sub.3 H OPh CH 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SePh CH 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SPh CH 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SO.sub.2 Ph CH 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SPh N 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 H SeCH.sub.3 N 1CH.sub.2 CH.sub.3 H H H O CH.sub.3 H SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H O CH.sub.3 H SePh CH 1CH.sub.2 CH.sub.3 H H H O CH.sub.3 H SPh CH 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H O OCH.sub.3 SPh SPh CH 1CH.sub.3 H H H S OCH.sub.3 H SeCH.sub.3 CH 0CH.sub.3 H H H S OCH.sub.3 H SePh CH 0CH.sub.3 H H H S OCH.sub.3 H SPh CH 0CH.sub.3 H H H S OCH.sub.3 H SO.sub.2 Ph CH 0CH.sub.3 H H H S OCH.sub.3 H SPh N 0CH.sub.3 H H H S OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.3 H H H S CH.sub.3 H SeCH.sub.3 CH 0CH.sub.3 H H H S CH.sub.3 H SePh CH 0CH.sub.3 CH.sub.3 H H S CH.sub.3 H SPh CH 0CH.sub.3 H H CH.sub.3 S CH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.3 H H H S CH.sub.3 SeCH.sub.3 SPh CH 0CH.sub.3 H H H S CH.sub.3 SPh SPh CH 0CH.sub.3 H H H S CH.sub.3 H OPh CH 0CH.sub.3 H H H S OCH.sub.3 H OPh CH 0CH.sub. 2 CH.sub.3 H H H S OCH.sub.3 H SeCH.sub.3 CH 0CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SePh CH 0CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SPh CH 0CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SO.sub.2 Ph CH 0CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SPh N 0CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SeCH.sub.3 N 0CH.sub.2 CH.sub.3 H H H S CH.sub.3 H SeCH.sub.3 CH 0CH.sub.2 CH.sub.3 H H H S CH.sub.3 H SePh CH 0CH.sub.2 CH.sub.3 H H H S CH.sub.3 H SPh CH 0CH.sub.2 CH.sub.3 H H H S OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.2 CH.sub.3 H H H S OCH.sub.3 SPh SPh CH 0CH.sub.3 H H H S OCH.sub.3 H SeCH.sub.3 CH 1CH.sub.3 H H H S OCH.sub.3 H SePh CH 1CH.sub.3 H H H S OCH.sub.3 H SPh CH 1CH.sub.3 H H H S OCH.sub.3 H SO.sub.2 Ph CH 1CH.sub.3 H H H S OCH.sub.3 H SPh N 1CH.sub.3 H H H S OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 1CH.sub.3 H H H S CH.sub.3 H SeCH.sub.3 CH 1CH.sub.3 H H H S CH.sub.3 H SePh CH 1CH.sub.3 CH.sub.3 H H S CH.sub.3 H SPh CH 1CH.sub.3 H H CH.sub.3 S CH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 1CH.sub.3 H H H S CH.sub.3 SeCH.sub.3 SPh CH 1CH.sub.3 H H H S CH.sub.3 SPh SPh CH 1CH.sub.3 H H H S CH.sub.3 H OPh CH 1CH.sub.3 H H H S OCH.sub.3 H OPh CH 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SePh CH 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SPh CH 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SO.sub.2 Ph CH 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SPh N 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 H SeCH.sub.3 N 1CH.sub.2 CH.sub.3 H H H S CH.sub.3 H SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H S CH.sub.3 H SePh CH 1CH.sub.2 CH.sub.3 H H H S CH.sub.3 H SPh CH 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H S OCH.sub.3 SPh SPh CH 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SeCH.sub.3 CH 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SePh CH 0CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh CH 0CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SO.sub.2 Ph CH 0CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh N 0CH.sub.3 H H H SO.sub.2 OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.3 H H H SO.sub.2 CH.sub.3 H SeCH.sub.3 CH 0CH.sub.3 H H H SO.sub.2 CH.sub.3 H SePh CH 0CH.sub.3 CH.sub.3 H H SO.sub.2 CH.sub.3 H SPh CH 0CH.sub.3 H H CH.sub.3 SO.sub.2 CH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.3 H H H SO.sub.2 CH.sub.3 SeCH.sub.3 SPh CH 0CH.sub.3 H H H SO.sub.2 CH.sub.3 SPh SPh CH 0CH.sub.3 H H H SO.sub.2 CH.sub.3 H OPh CH 0CH.sub.3 H H H SO.sub.2 OCH.sub.3 H OPh CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SeCH.sub.3 CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SePh CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SO.sub.2 Ph CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh N 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SeCH.sub.3 N 0CH.sub.2 CH.sub.3 H H H SO.sub.2 CH.sub.3 H SeCH.sub. 3 CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 CH.sub.3 H SePh CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 CH.sub.3 H SPh CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 0CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 SPh SPh CH 0CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SeCH.sub.3 CH 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SePh CH 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh CH 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SO.sub.2 Ph CH 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh N 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CH 1CH.sub.3 H H H SO.sub.2 CH.sub.3 H SeCH.sub.3 CH 1CH.sub.3 H H H SO.sub.2 CH.sub.3 H SePh CH 1CH.sub.3 CH.sub.3 H H SO.sub.2 CH.sub.3 H SPh CH 1CH.sub.3 H H CH.sub.3 SO.sub.3 CH.sub.3 SeCH.sub.3 SeCH.sub. 3 CH 1CH.sub.3 H H H SO.sub.2 CH.sub.3 SeCH.sub.3 SPh CH 1CH.sub.3 H H H SO.sub.2 CH.sub.3 SPh SPh CH 1CH.sub.3 H H H SO.sub.2 CH.sub.3 H OPh CH 1CH.sub.3 H H H SO.sub.2 OCH.sub.3 H OPh CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SePh CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SO.sub.2 Ph CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SPh N 1CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H SeCH.sub.3 N 1CH.sub.2 CH.sub.3 H H H SO.sub.2 CH.sub.3 H SeCH.sub.3 CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 CH.sub.3 H SePh CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 CH.sub.3 H SPh CH 1CH.sub.2 CH.sub.3 H H H SO.sub.2 OCH.sub.3 H OSi(CH.sub.3).sub.3 CH 0__________________________________________________________________________ TABLE 5b______________________________________ ##STR63##R.sub.7 R.sub.8 R.sub.9 m Q.sub.1 R X.sub.1 m.p. (.degree.C.)______________________________________CH.sub.3 H H 0 S H OCH.sub.3CH.sub.3 H H 0 S H CH.sub.3CH.sub.3 H H 0 S H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H H 0 S H OCH.sub.3CH.sub.2 CH.sub.3 H H 0 S H CH.sub.3CH.sub.2 CH.sub.3 H H 0 S H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 S H OCH.sub.3CH.sub.3 CH.sub.3 H 0 S H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 S H CH.sub.3CH.sub.3 H CH.sub.3 0 S H CH.sub.3CH.sub.3 H CH.sub.3 0 S H OCH.sub.3CH.sub.3 H CH.sub.3 0 S H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H CH.sub.3 0 S H OCH.sub.3CH.sub.3 H H 1 S H OCH.sub.3CH.sub.3 H H 1 S H CH.sub.3CH.sub.3 H H 1 S H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H H 1 S H OCH.sub.3CH.sub.2 CH.sub.3 H H 1 S H CH.sub.3CH.sub.2 CH.sub.3 H H 1 S H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 1 S H OCH.sub.3CH.sub.3 CH.sub.3 H 1 S H OCH.sub.2 CH.sub.3CH.sub.3 H H 1 S CH.sub.3 OCH.sub.3CH.sub.3 H H 0 O H OCH.sub.3CH.sub.3 H H 0 O H CH.sub.3CH.sub.3 H H 0 O H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H H 0 O H OCH.sub.3CH.sub.2 CH.sub.3 H H 0 O H CH.sub.3CH.sub.2 CH.sub.3 H H 0 O H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 O H OCH.sub.3CH.sub.3 CH.sub.3 H 0 O H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 O H CH.sub.3CH.sub.3 H CH.sub.3 0 O H CH.sub.3CH.sub.3 H CH.sub.3 0 O H OCH.sub.3CH.sub.3 H CH.sub.3 0 O H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H CH.sub.3 0 O H OCH.sub.3CH.sub.3 H H 1 O H OCH.sub.3CH.sub.3 H H 1 O H CH.sub.3CH.sub.3 H H 1 O H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H H 1 O H OCH.sub.3CH.sub.2 CH.sub.3 H H 1 O H CH.sub.3CH.sub.2 CH.sub.3 H H 1 O H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 1 O H OCH.sub.3CH.sub.3 CH.sub.3 H 1 O H OCH.sub.2 CH.sub.3CH.sub.3 H H 1 O CH.sub.3 OCH.sub.3CH.sub.3 H H 0 SO.sub.2 H OCH.sub.3CH.sub.3 H H 0 SO.sub.2 H CH.sub.3CH.sub.3 H H 0 SO.sub.2 H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H H 0 SO.sub.2 H OCH.sub.3CH.sub.2 CH.sub.3 H H 0 SO.sub.2 H CH.sub.3CH.sub.2 CH.sub.3 H H 0 SO.sub.2 H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 SO.sub.2 H OCH.sub.3CH.sub.3 CH.sub.3 H 0 SO.sub.2 H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 SO.sub.2 H CH.sub.3CH.sub.3 H CH.sub.3 0 SO.sub.2 H CH.sub.3CH.sub.3 H CH.sub.3 0 SO.sub.2 H OCH.sub.3CH.sub.3 H CH.sub.3 0 SO.sub.2 H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H CH.sub.3 0 SO.sub.2 H OCH.sub.3CH.sub.3 H H 1 SO.sub.2 H OCH.sub.3CH.sub.3 H H 1 SO.sub.2 H CH.sub.3CH.sub.3 H H 1 SO.sub.2 H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H H 1 SO.sub.2 H OCH.sub.3CH.sub.2 CH.sub.3 H H 1 SO.sub.2 H CH.sub. 3CH.sub.2 CH.sub.3 H H 1 SO.sub.2 H OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 1 SO.sub.2 H OCH.sub.3CH.sub.3 CH.sub.3 H 1 SO.sub.2 H OCH.sub.2 CH.sub.3CH.sub.3 H H 1 SO.sub.2 CH.sub.3 OCH.sub.3______________________________________ TABLE 5c______________________________________ ##STR64##R.sub.7 R.sub.8 R.sub.9 Q.sub.1 R m m.p. (.degree.C.)______________________________________CH.sub.3 H H O H 0CH.sub.3 CH.sub.3 H O H 0CH.sub.3 H CH.sub.3 O H 0CH.sub.2 CH.sub.3 H H O H 0CH.sub.2 CH.sub.3 H CH.sub.3 O H 0CH.sub.3 CH.sub.3 CH.sub.3 O H 0CH.sub.3 H H O CH.sub.3 0CH.sub.3 H H O H 1CH.sub.3 CH.sub.3 H O H 1CH.sub.2 CH.sub.3 H H O H 1CH.sub.3 H H S H 0CH.sub.3 CH.sub.3 H S H 0CH.sub.3 H CH.sub.3 S H 0CH.sub.2 CH.sub.3 H H S H 0CH.sub.2 CH.sub.3 H CH.sub.3 S H 0CH.sub.3 CH.sub.3 CH.sub.3 S H 0CH.sub.3 H H S CH.sub.3 0CH.sub.3 H H S H 1CH.sub.3 CH.sub.3 H S H 1CH.sub.2 CH.sub.3 H H S H 1CH.sub.3 H H SO.sub.2 H 0CH.sub.3 CH.sub.3 H SO.sub.2 H 0CH.sub.3 H CH.sub.3 SO.sub.2 H 0CH.sub.2 CH.sub.3 H H SO.sub.2 H 0CH.sub.2 CH.sub.3 H CH.sub.3 SO.sub.2 H 0CH.sub.3 CH.sub.3 CH.sub.3 SO.sub.2 H 0CH.sub.3 H H SO.sub.2 CH.sub.3 0CH.sub.3 H H SO.sub.2 H 1CH.sub.3 CH.sub.3 H SO.sub.2 H 1CH.sub.2 CH.sub.3 H H SO.sub.2 H 1______________________________________ TABLE 5d______________________________________ ##STR65##R.sub.7 R.sub.8 R.sub.9 Q.sub.1 R m m.p. (.degree.C.)______________________________________CH.sub.3 H H O H 0CH.sub.3 CH.sub.3 H O H 0CH.sub.3 H CH.sub.3 O H 0CH.sub.2 CH.sub.3 H H O H 0CH.sub.2 CH.sub.3 H CH.sub.3 O H 0CH.sub.3 CH.sub.3 CH.sub.3 O H 0CH.sub.3 H H O CH.sub.3 0CH.sub.3 H H O H 1CH.sub.3 CH.sub.3 H O H 1CH.sub.2 CH.sub.3 H H O H 1CH.sub.3 H H S H 0CH.sub.3 CH.sub.3 H S H 0CH.sub.3 H CH.sub.3 S H 0CH.sub.2 CH.sub.3 H H S H 0CH.sub.2 CH.sub.3 H CH.sub.3 S H 0CH.sub.3 CH.sub.3 CH.sub.3 S H 0CH.sub.3 H H S CH.sub.3 0CH.sub.3 H H S H 1CH.sub.3 CH.sub.3 H S H 1CH.sub.2 CH.sub.3 H H S H 1CH.sub.3 H H SO.sub.2 H 0CH.sub.3 CH.sub.3 H SO.sub.2 H 0CH.sub.3 H CH.sub.3 SO.sub.2 H 0CH.sub.2 CH.sub.3 H H SO.sub.2 H 0CH.sub.2 CH.sub.3 H CH.sub.3 SO.sub.2 H 0CH.sub.3 CH.sub.3 CH.sub.3 SO.sub.2 H 0CH.sub.3 H H SO.sub.2 CH.sub.3 0CH.sub.3 H H SO.sub.2 H 1CH.sub.3 CH.sub.3 H SO.sub.2 H 1CH.sub.2 CH.sub.3 H H SO.sub.2 H 1______________________________________ TABLE 5e__________________________________________________________________________ ##STR66##Q.sub.1 m R.sub.7 R.sub.8 R.sub.9 R X Z G m.p. (.degree.C.)__________________________________________________________________________O 0 H H H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)O 0 CH.sub.3 H H H OCH.sub.3 N CH(OCH.sub.3).sub.2S 1 H H H H OCH.sub.3 CH CH(OCH.sub.3).sub.2S 0 CH.sub.3 H H H OCH.sub.3 CH C.sub.6 H.sub.5SO.sub.2 0 H H H H OCH.sub.3 CH CH( OCH.sub.2 CH.sub.2 O)SO.sub.2 0 CH.sub.3 CH.sub.3 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)SO.sub.2 1 H H H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)S 0 H H H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)O 0 H H H H OCH.sub.3 CH CH(OCH.sub.3).sub.2S 0 H H H H OCH.sub.3 CH C.sub.6 H.sub.5SO.sub.2 1 H H H H OCH.sub.3 CH CH(OCH.sub.3).sub.2__________________________________________________________________________ TABLE 6a______________________________________ ##STR67## m.p.R.sub.10 R.sub.11 Q.sub.2 R X T Y Z (.degree.C.)______________________________________H H O H OCH.sub.3 H SeCH.sub.3 CHH H O H OCH.sub.3 H SePh CHH H O H OCH.sub.3 H SPh CHCH.sub.3 H O H OCH.sub.3 H SeCH.sub.3 CHCH.sub.3 H O H OCH.sub.3 H SePh CHCH.sub.3 H O H OCH.sub.3 H SPh CHCH.sub.3 H O H OCH.sub.3 H SO.sub.2 Ph CHCH.sub.3 H O H CH.sub.3 H SPh CHCH.sub.3 H O H CH.sub.3 H SPh NCH.sub.3 H O H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 H O H OCH.sub.3 SPh SPh CHH CH.sub.3 O H OCH.sub.3 H SeCH.sub.3 CHH CH.sub.3 O H OCH.sub.3 H SePh CHH CH.sub.3 O H OCH.sub.3 H SPh CHH CH.sub.3 O H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 CH.sub.3 O H OCH.sub.3 H SeCH.sub.3 CHCH.sub.3 CH.sub.3 O H OCH.sub.3 H SPh CHCH.sub.3 H O CH.sub.3 OCH.sub.3 H SeCH.sub.3 CHH H S H OCH.sub.3 H SeCH.sub.3 CHH H S H OCH.sub.3 H SePh CHH H S H OCH.sub.3 H SPh CHCH.sub.3 H S H OCH.sub.3 H SeCH.sub.3 CHCH.sub.3 H S H OCH.sub.3 H SePh CHCH.sub.3 H S H OCH.sub.3 H SPh CHCH.sub.3 H S H OCH.sub.3 H SO.sub.2 Ph CHCH.sub.3 H S H CH.sub.3 H SPh CHCH.sub.3 H S H CH.sub.3 H SPh NCH.sub.3 H S H CH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 H S H OCH.sub.3 SPh SPh CHH CH.sub.3 S H OCH.sub.3 H SeCH.sub.3 CHH CH.sub.3 S H OCH.sub.3 H SePh CHH CH.sub.3 S H OCH.sub.3 H SPh CHH CH.sub.3 S H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 CH.sub.3 S H OCH.sub.3 H SeCH.sub.3 CHCH.sub.3 CH.sub.3 S H OCH.sub.3 H SPh CHCH.sub.3 H S CH.sub.3 OCH.sub.3 H SeCH.sub.3 CHCH.sub.3 H O CH.sub.3 OCH.sub.3 H OSi(CH.sub.3).sub.3 CHCH.sub.3 H S CH.sub.3 OCH.sub.3 H OSi(CH.sub.3).sub.3 NH H S CH.sub.3 OCH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.3 N______________________________________ TABLE 6b______________________________________ ##STR68##R.sub.10 R.sub.11 Q.sub.2 R X.sub.1 m.p. (.degree.C.)______________________________________H H O H OCH.sub.3CH.sub.3 H O H OCH.sub.3CH.sub.3 H O H CH.sub.3CH.sub.3 H O H OCH.sub.2 CH.sub.3H CH.sub.3 O H OCH.sub.3CH.sub.3 CH.sub.3 O H OCH.sub.3CH.sub.3 H O CH.sub.3 OCH.sub.3H H S H OCH.sub.3CH.sub.3 H S H OCH.sub.3CH.sub.3 H S H CH.sub.3CH.sub.3 H S H OCH.sub.2 CH.sub.3H CH.sub.3 S H OCH.sub.3CH.sub.3 CH.sub.3 S H OCH.sub.3CH.sub.3 H S CH.sub.3 OCH.sub.3______________________________________ TABLE 6c______________________________________ ##STR69##R.sub.10 R.sub.11 Q.sub.1 R A m.p. (.degree.C.)______________________________________CH.sub.3 H O H A-3H H O H A-3CH.sub.3 CH.sub.3 O H A-3CH.sub.3 H O CH.sub.3 A-3CH.sub.3 H S H A-3H H S H A-3CH.sub.3 CH.sub.3 S H A-3H CH.sub.3 S H A-3H H O H A-4CH.sub.3 H O H A-4CH.sub.3 CH.sub.3 O H A-4CH.sub.3 H O CH.sub.3 A-4H CH.sub.3 O H A-4H H S H A-4CH.sub.3 H S H A-4CH.sub.3 CH.sub.3 S H A-4H CH.sub.3 S H A-4______________________________________ TABLE 6d______________________________________ ##STR70##R.sub.10 R.sub.11 Q.sub.1 R X.sub.1 E Z m.p. (.degree.C.)______________________________________H H O H OCH.sub.3 F CHH H O H OCH.sub.3 Cl CHCH.sub.3 H O H OCH.sub.3 F CHCH.sub.3 H O H CH.sub.3 F CHCH.sub.3 H O H CH.sub.3 F NH CH.sub.3 O H OCH.sub.3 F CHH CH.sub.3 O H OCH.sub.3 Br CHH H S H OCH.sub.3 F CHCH.sub.3 H S H OCH.sub.3 F CHCH.sub.3 H S H OCH.sub.3 Cl CHCH.sub.3 H S H CH.sub.3 Br CHCH.sub.3 CH.sub.3 S H OCH.sub.3 F CHCH.sub.3 H S H OCH.sub.3 F N______________________________________ TABLE 6e______________________________________ ##STR71## m.p.Q.sub.2 R.sub.10 R.sub.11 R X Z G (.degree.C.)______________________________________O H H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)O H H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)O CH.sub.3 CH.sub.3 H OCH.sub.3 N CH(OCH.sub.2 CH.sub.2 O)O CH.sub.3 H H OCH.sub.3 CH CH(OCH.sub.3).sub.2S H H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)S CH.sub.3 H H OCH.sub.3 CH C.sub.6 H.sub.5S H H H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)S H H H OCH.sub.3 CH CH(OCH.sub.3).sub.2______________________________________ TABLE 7a__________________________________________________________________________ ##STR72##R.sub.9 R.sub.12 R m X T Y Z m.p. (.degree.C.)__________________________________________________________________________H CH.sub.3 H 0 OCH.sub.3 H SeCH.sub.3 CHH CH.sub.3 H 0 OCH.sub.3 H SePh CHH CH.sub.3 H 0 OCH.sub.3 H SPh CHH CH.sub.3 H 0 OCH.sub.3 H SO.sub.2 Ph CHH CH.sub.3 H 0 OCH.sub.3 H OPh CHH CH.sub.3 H 0 CH.sub.3 H SeCH.sub.3 CHH CH.sub.3 H 0 CH.sub.3 H SePh CHH CH.sub.3 H 0 CH.sub.3 H SPh CHH CH.sub.3 H 0 OCH.sub.3 H SeCH.sub.3 NH CH.sub.3 H 0 OCH.sub.3 H SPh NH CH.sub.3 H 0 OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHH CH.sub.3 H 0 OCH.sub.3 SPh SPh CHCH.sub.3 CH.sub.3 H 0 OCH.sub.3 H SPh CHH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SeCH.sub.3 CHH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SePh CHH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SPh CHH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SO.sub.2 Ph CHH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SPh NH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H OPh CHH CH.sub.2 CH.sub.3 H 0 CH.sub.3 H SeCH.sub.3 CHH CH.sub.2 CH.sub.3 H 0 CH.sub.3 H SePh CHH CH.sub.2 CH.sub.3 H 0 CH.sub.3 H SPh CHH CH.sub.2 CH.sub.3 H 0 CH.sub.3 H SPh NH CH.sub.3 H 0 OCH.sub.2 CH.sub.3 H SePh CHH CH.sub.3 H 0 Cl H SPh CHH CH.sub.3 H 0 F H SPh CHH CH.sub.3 H 0 Br H SePh CHH CH.sub.3 H 0 CF.sub.3 H SePh CHH CH.sub.3 H 0 OCHF.sub.2 H SPh CHCH.sub.3 CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SPh CHH CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SeCH.sub.3 CHH CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SePh CHH CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SPh CHH CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H SO.sub.2 Ph CHH CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.3 H OPh CHH CH.sub.3 CH.sub.3 0 OCH.sub.3 H SPh CHH CH.sub.3 H 1 OCH.sub.3 H SeCH.sub.3 CHH CH.sub.3 H 1 OCH.sub.3 H SePh CHH CH.sub.3 H 1 OCH.sub.3 H SPh CHH CH.sub.3 H 1 OCH.sub.3 H SO.sub.2 Ph CHH CH.sub.3 H 1 OCH.sub.3 H OPh CHH CH.sub.3 H 1 CH.sub.3 H SeCH.sub.3 CHH CH.sub.3 H 1 CH.sub.3 H SePh CHH CH.sub.3 H 1 CH.sub.3 H SPh CHH CH.sub.3 H 1 OCH.sub.3 H SeCH.sub.3 NH CH.sub.3 H 1 OCH.sub.3 H SPh NH CH.sub.3 H 1 OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHH CH.sub.3 H 1 OCH.sub.3 SPh SPh CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SeCH.sub.3 CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SePh CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SPh CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SO.sub.2 Ph CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SPh NH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H OPh CHH CH.sub.2 CH.sub.3 H 1 CH.sub.3 H SeCH.sub.3 CHH CH.sub.2 CH.sub.3 H 1 CH.sub.3 H SePh CHH CH.sub.2 CH.sub.3 H 1 CH.sub.3 H SPh CHH CH.sub.2 CH.sub.3 H 1 CH.sub.3 H SPh NH CH.sub.3 H 1 OCH.sub.2 CH.sub.3 H SePh CHH CH.sub.3 H 1 Cl H SPh CHH CH.sub.3 H 1 F H SPh CHH CH.sub.3 H 1 Br H SePh CHH CH.sub.3 H 1 CF.sub.3 H SePh CHH CH.sub.3 H 1 OCHF.sub.2 H SPh CHH CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SeCH.sub.3 CHH CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SePh CHH CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SPh CHH CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H SO.sub.2 Ph CHH CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.3 H OPh CHH CH.sub.3 H 0 OCH.sub.3 H OSi(CH.sub.3).sub.3 CHH CH.sub.3 H 1 OCH.sub.3 H OSi(CH.sub.3).sub.3 CHH CH.sub.3 H 1 OCH.sub.3 H CH.sub.2 OH CHCH.sub.3 CH.sub.3 H 0 CH.sub.3 H CH.sub.2 OSi(CH.sub.3).sub.2 N__________________________________________________________________________ TABLE 7b______________________________________ ##STR73##R.sub.9 R.sub.12 R m X.sub.1 m.p. (.degree.C.)______________________________________H CH.sub.3 H 0 CH.sub.3H CH.sub.3 H 0 OCH.sub.3H CH.sub.3 H 0 OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 OCH.sub.3H CH.sub.2 CH.sub.3 H 0 CH.sub.3H CH.sub.2 CH.sub.3 H 0 OCH.sub.3H CH.sub.2 CH.sub.3 H 0 OCH.sub.2 CH.sub.3H CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.3H CH.sub.2 CH.sub.2 CH.sub.3 H 0 CH.sub.3H CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.2 CH.sub.3H CH.sub.3 H 1 CH.sub.3H CH.sub.3 H 1 OCH.sub.3H CH.sub.3 H 1 OCH.sub.2 CH.sub.3CH.sub.3 CH.sub.3 H 0 CH.sub.3H CH.sub.2 CH.sub.3 H 1 CH.sub.3H CH.sub.2 CH.sub.3 H 1 OCH.sub.3H CH.sub.2 CH.sub.3 H 1 OCH.sub.2 CH.sub.3H CH.sub.2 CH.sub.2 CH.sub.3 H 1 CH.sub.3H CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.3H CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.2 CH.sub.3H CH.sub.3 CH.sub.3 0 OCH.sub.3______________________________________ TABLE 7c______________________________________ ##STR74##R.sub.9 R.sub.12 R m m.p. (.degree.C.)______________________________________H CH.sub.3 H 0H CH.sub.2 CH.sub.3 H 0H CH.sub.2 CH.sub.2 CH.sub.3 H 0CH.sub.3 CH.sub.3 H 0H CH.sub.3 CH.sub.3 0CH.sub.3 CH.sub.2 CH.sub.3 H 0H CH.sub.3 H 1H CH.sub.2 CH.sub.3 H 1H CH.sub.2 CH.sub.2 CH.sub.3 H 1H CH.sub.3 CH.sub.3 1______________________________________ TABLE 7d______________________________________ ##STR75##R.sub.9 R.sub.12 R m X.sub.1 E Z m.p. (.degree.C.)______________________________________H CH.sub.3 H 0 OCH.sub.3 Cl CHH CH.sub.3 H 0 OCH.sub.3 Br CHH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 Cl CHH CH.sub.2 CH.sub.3 H 0 OCH.sub.3 Br CHH CH.sub.2 CH.sub.2 CH.sub.3 H 0 OCH.sub.3 Cl CHH CH.sub.3 H 0 OCH.sub.3 Br NH CH.sub.3 H 1 OCH.sub.3 Cl CHH CH.sub.3 H 1 OCH.sub.3 Br CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 Cl CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.3 Br CHH CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.3 Cl CHH CH.sub.3 H 1 OCH.sub.2 CH.sub.3 Br CHH CH.sub.2 CH.sub.3 H 1 OCH.sub.2 CH.sub.3 Cl CHH CH.sub.2 CH.sub.2 CH.sub.3 H 1 OCH.sub.2 CH.sub.3 Cl CHH CH.sub.3 H 1 OCH.sub.3 Br N______________________________________ TABLE 7e______________________________________ ##STR76## m.p.R.sub.9 R.sub.12 R m X Z G (.degree.C.)______________________________________H CH.sub.3 H 0 OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CH.sub.3 CH.sub.3 H 0 CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)H CH.sub.3 H 1 OCH.sub.3 N CH(OCH.sub.2 CH.sub.2 O)H CH.sub.3 H 1 OCH.sub.3 CH CH(OCH.sub.3).sub.2H C.sub.2 H.sub.5 H 0 OCH.sub.3 CH C.sub.6 H.sub.5H C.sub.3 H.sub.7 H 0 OCH.sub.3 CH CH(OCH.sub.3).sub.2H CH.sub.3 H 0 OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)______________________________________ TABLE 8a______________________________________ ##STR77## m.p.L m R.sub.9 R X T Y Z (.degree.C.)______________________________________L-11 0 H H OCH.sub.3 H SeCH.sub.3 CHL-11 0 H H OCH.sub.3 H SePh CHL-11 0 H H OCH.sub.3 H SPh CHL-11 0 H H OCH.sub.3 H SO.sub.2 Ph CHL-11 0 H H OCH.sub.3 H OPh CHL-11 0 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-11 0 H H OCH.sub.3 SPh SPh CHL-11 0 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHL-11 0 H H OCH.sub.3 H SeCH.sub.3 NL-11 0 H H OCH.sub.3 H SPh NL-11 0 H H CH.sub.3 H SeCH.sub.3 CHL-11 0 H H CH.sub.3 H SePh CHL-11 0 H H CH.sub.3 H SPh CHL-11 0 H H CH.sub.3 H SO.sub.2 Ph CHL-11 0 H H OCH.sub.2 CH.sub.3 H SPh CHL-11 0 H H OCHF.sub.2 H SPh CHL-11 0 H H Cl H SePh CHL-11 0 H H CF.sub.3 H SPh CHL-11 0 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-11 0 CH.sub.3 H OCH.sub.3 H SPh CHL-11 1 H H OCH.sub.3 H SeCH.sub.3 CHL-11 1 H H OCH.sub.3 H SePh CHL-11 1 H H OCH.sub.3 H SPh CHL-11 1 H H OCH.sub.3 H SO.sub.2 Ph CHL-11 1 H H OCH.sub.3 H OPh CHL-11 1 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-11 1 H H OCH.sub.3 SPh SPh CHL-11 1 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHL-11 1 H H OCH.sub.3 H SeCH.sub.3 NL-11 1 H H OCH.sub.3 H SPh NL-11 1 H H CH.sub.3 H SeCH.sub.3 CHL-11 1 H H CH.sub.3 H SePh CHL-11 1 H H CH.sub.3 H SPh CHL-11 1 H H CH.sub.3 H SO.sub.2 Ph CHL-11 1 H H OCH.sub.2 CH.sub.3 H SPh CHL-11 1 H H OCHF.sub.2 H SPh CHL-11 1 H H Cl H SePh CHL-11 1 H H CF.sub.3 H SPh CHL-12 0 H H OCH.sub.3 H SeCH.sub.3 CHL-12 0 H H OCH.sub.3 H SePh CHL-12 0 H H OCH.sub.3 H SPh CHL-12 0 H H OCH.sub.3 H SO.sub.2 Ph CHL-12 0 H H OCH.sub.3 H OPh CHL-12 0 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-12 0 H H OCH.sub.3 SPh SPh CHL-12 0 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHL-12 0 H H OCH.sub.3 H SeCH.sub.3 NL-12 0 H H OCH.sub.3 H SPh NL-12 0 H H CH.sub.3 H SeCH.sub.3 CHL-12 0 H H CH.sub.3 H SePh CHL-12 0 H H CH.sub.3 H SPh CHL-12 0 H H CH.sub.3 H SO.sub.2 Ph CHL-12 0 H H OCH.sub.2 CH.sub.3 H SPh CHL-12 0 H H OCHF.sub.2 H SPh CHL-12 0 H H Cl H SePh CHL-12 0 H H CF.sub.3 H SPh CHL-12 0 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-12 0 CH.sub.3 H OCH.sub.3 H SPh CHL-12 1 H H OCH.sub.3 H SeCH.sub.3 CHL-12 1 H H OCH.sub.3 H SePh CHL-12 1 H H OCH.sub.3 H SPh CHL-12 1 H H OCH.sub.3 H SO.sub.2 Ph CHL-12 1 H H OCH.sub.3 H OPh CHL-12 1 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-12 1 H H OCH.sub.3 SPh SPh CHL-12 1 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHL-12 1 H H OCH.sub.3 H SeCH.sub.3 NL-12 1 H H OCH.sub.3 H SPh NL-12 1 H H CH.sub.3 H SeCH.sub.3 CHL-12 1 H H CH.sub.3 H SePh CHL-12 1 H H CH.sub.3 H SPh CHL-12 1 H H CH.sub.3 H SO.sub.2 Ph CHL-12 1 H H OCH.sub.2 CH.sub.3 H SPh CHL-12 1 H H OCHF.sub.2 H SPh CHL-12 1 H H Cl H SePh CHL-12 1 H H CF.sub.3 H SPh CHL-13 0 H H OCH.sub.3 H SeCH.sub.3 CHL-13 0 H H OCH.sub.3 H SePh CHL-13 0 H H OCH.sub.3 H SPh CHL-13 0 H H OCH.sub.3 H SO.sub.2 Ph CHL-13 0 H H OCH.sub.3 H OPh CHL-13 0 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-13 0 H H OCH.sub.3 SPh SPh CHL-13 0 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHL-13 0 H H OCH.sub.3 H SeCH.sub.3 NL-13 0 H H OCH.sub.3 H SPh NL-13 0 H H CH.sub.3 H SeCH.sub.3 CHL-13 0 H H CH.sub.3 H SePh CHL-13 0 H H CH.sub.3 H SPh CHL-13 0 H H CH.sub.3 H SO.sub.2 Ph CHL-13 0 H H OCH.sub.2 CH.sub.3 H SPh CHL-13 0 H H OCHF.sub.2 H SPh CHL-13 0 H H Cl H SePh CHL-13 0 H H CF.sub.3 H SPh CHL-13 0 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-13 0 CH.sub.3 H OCH.sub.3 H SPh CHL-13 1 H H OCH.sub.3 H SeCH.sub.3 CHL-13 1 H H OCH.sub.3 H SePh CHL-13 1 H H OCH.sub.3 H SPh CHL-13 1 H H OCH.sub.3 H SO.sub.2 Ph CHL-13 1 H H OCH.sub.3 H OPh CHL-13 1 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-13 1 H H OCH.sub.3 SPh SPh CHL-13 1 H H OCH.sub.3 SCH.sub.3 SeCH.sub.3 CHL-13 1 H H OCH.sub.3 H SeCH.sub.3 NL-13 1 H H OCH.sub.3 H SPh NL-13 1 H H CH.sub.3 H SeCH.sub.3 CHL-13 1 H H CH.sub.3 H SePh CHL-13 1 H H CH.sub.3 H SPh CHL-13 1 H H CH.sub.3 H SO.sub.2 Ph CHL-13 1 H H OCH.sub.2 CH.sub.3 H SPh CHL-13 1 H H OCHF.sub.2 H SPh CHL-13 1 H H Cl H SePh CHL-13 1 H H CF.sub.3 H SPh CHL-11 0 H H OCH.sub.3 H CH.sub.2 OH CHL-12 1 H H OCH.sub.3 H CH.sub.2 OH NL-13 1 H H OCH.sub.3 H OSi(CH.sub.3).sub.3 CH______________________________________ TABLE 8b______________________________________ ##STR78##L R.sub.9 R X.sub.1 m m.p. (.degree.C.)______________________________________L-11 H H CH.sub.3 0L-11 H H OCH.sub.3 0L-11 H H OCH.sub.2 CH.sub.3 0L-11 CH.sub.3 H OCH.sub.3 0L-11 H H CH.sub.3 1L-11 H H OCH.sub.3 1L-11 H H OCH.sub.2 CH.sub.3 1L-12 H H CH.sub.3 0L-12 H H OCH.sub.3 0L-12 H H OCH.sub.2 CH.sub.3 0L-12 CH.sub.3 H OCH.sub.3 0L-12 H H CH.sub.3 1L-12 H H OCH.sub.3 1L-12 H H OCH.sub.2 CH.sub.3 1L-13 H H CH.sub.3 0L-13 H H OCH.sub.3 0L-13 H H OCH.sub.2 CH.sub.3 0L-13 H H CH.sub.3 1L-13 H H OCH.sub.3 1L-13 H H OCH.sub.2 CH.sub.3 1______________________________________ TABLE 8c______________________________________ ##STR79##L R.sub.9 R m m.p. (.degree.C.)______________________________________L-11 H H 0L-11 CH.sub.3 H 0L-11 CH.sub.3 CH.sub.3 0L-11 H H 1L-11 H CH.sub.3 1L-12 H H 0L-12 CH.sub.3 H 0L-12 CH.sub.3 CH.sub.3 0L-12 H H 1L-12 H CH.sub.3 1L-13 H H 0L-13 CH.sub.3 H 0L-13 H H 1______________________________________ TABLE 8d______________________________________ ##STR80##L R.sub.9 R m X.sub.1 E Z m.p. (.degree.C.)______________________________________L-12 H H 0 OCH.sub.3 Cl CHL-12 H H 0 OCH.sub.3 Br CHL-12 H H 0 CH.sub.3 Cl CHL-12 H H 0 CH.sub.2 CH.sub.3 Br CHL-12 H H 0 OCH.sub.3 Cl NL-12 H H 1 OCH.sub.3 Cl CHL-12 H H 1 OCH.sub.3 Br CHL-12 H H 1 CH.sub.3 Cl CHL-12 H H 1 CH.sub.2 CH.sub.3 Br CHL-12 H H 1 OCH.sub.3 Cl NL-12 CH.sub.3 H 0 OCH.sub.3 Cl CHL-12 H CH.sub.3 0 OCH.sub.3 Cl CHL-13 H H 0 OCH.sub.3 Cl CHL-13 H H 0 OCH.sub.3 Br CHL-13 H H 1 OCH.sub.3 Cl CHL-13 H H 1 OCH.sub.3 Br CH______________________________________ TABLE 8e______________________________________ ##STR81## m.p.L R.sub.9 R m X Z G (.degree.C.)______________________________________L-11 H H 0 OCH.sub.3 CH CH(OCH.sub.3).sub.2L-11 H H 0 CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-11 H H 1 OCH.sub.3 N CH(OCH.sub.2 CH.sub.2 O)L-11 CH.sub.3 H 1 OCH.sub.3 CH CH(OCH.sub.3).sub.2L-12 H H 0 OCH.sub.3 CH CH(OCH.sub.3).sub.2L-12 H H 1 OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-13 H H 0 OCH.sub.3 CH C.sub.6 H.sub.5L-13 H H 1 OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)______________________________________ TABLE 9a______________________________________ ##STR82##R.sub.12 R X T Y Zm.p. (.degree.C).______________________________________CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCH.sub.3 H OCH.sub.3 H SePh CHCH.sub.3 H CH.sub.3 H SPh CHCH.sub.3 H CH.sub.3 H SO.sub.2 Ph CHCH.sub.3 H OCH.sub.3 H OPh CHCH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.3 H OCH.sub.3 SPh SPh CHCH.sub.3 H OCH.sub.3 H SPh NCH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCH.sub.2 CH.sub.3 H OCH.sub.3 H SPh CHCH.sub.2 CH.sub.3 H OCH.sub.3 H OPh CHCH.sub.2 CH.sub.3 H CH.sub.3 H SePh CHCH.sub.2 CH.sub.3 H CH.sub.3 H SO.sub.2 Ph CHCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H OPh CHCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H SPh NCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SPh SPh NCH.sub.3 H Cl H SPh CHCH.sub.3 H CF.sub.3 H SePH CHCH.sub.3 H OCF.sub.2 H H OPh CHCH.sub.3 H OCH.sub.3 H CH.sub.2 OH CHCH.sub.2 CH.sub.3 H CH.sub.3 SCH.sub.3 CH.sub.2 OSi(CH.sub.3).sub.3 N______________________________________ TABLE 9b______________________________________ ##STR83##R.sub.12 R X.sub.1 m.p. (.degree.C.)______________________________________CH.sub.3 H OCH.sub.3CH.sub.3 H CH.sub.3CH.sub.3 H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.3 H OCH.sub.3CH.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3CH.sub.3 CH.sub.3 OCH.sub.3______________________________________ TABLE 9c______________________________________ ##STR84##R.sub.12 R m.p. (.degree.C.)______________________________________CH.sub.3 HCH.sub.2 CH.sub.3 HCH.sub.2 CH.sub.2 CH.sub.3 HCH.sub.3 CH.sub.3______________________________________ TABLE 9d______________________________________ ##STR85##R.sub.12 R X.sub.1 E Z m.p. (.degree.C.)______________________________________CH.sub.3 H CH.sub.3 Cl CHCH.sub.3 H CH.sub.3 Br CHCH.sub.3 H OCH.sub.3 Cl CHCH.sub.3 H OCH.sub.3 Cl NCH.sub.3 H OCH.sub.3 Br NCH.sub.2 CH.sub.3 H CH.sub.3 Cl CHCH.sub.2 CH.sub.3 H OCH.sub.3 Cl CHCH.sub.2 CH.sub.3 H OCH.sub.3 Br CHCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 Cl CHCH.sub.3 CH.sub.3 OCH.sub.3 Cl CH______________________________________ TABLE 9e______________________________________ ##STR86##R.sub.12 R X Z G m.p. (.degree.C.)______________________________________CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CH.sub.3 H CH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)C.sub.2 H.sub.5 H OCH.sub.3 N CH(OCH.sub.3).sub.2C.sub.2 H.sub.5 H CH.sub.3 CH CH(OCH.sub.3).sub.2C.sub.3 H.sub.7 - -n H OCH.sub.3 CH CH(OCH.sub.3).sub.2CH.sub.3 CH.sub.3 OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)CH.sub.3 H OCH.sub.3 CH C.sub.6 H.sub.5______________________________________ TABLE 10a__________________________________________________________________________ ##STR87##L R.sub.13 R.sub.14 R X T Y Z m.p. (.degree.C.)__________________________________________________________________________L-15 H -- H OCH.sub.3 H SeCH.sub.3 CHL-15 H -- H OCH.sub.3 H SePh CHL-15 H -- H OCH.sub.3 H SPh CHL-15 H -- H OCH.sub.3 H OPh CHL-15 H -- H CH.sub.3 H SPh CHL-15 H -- H OCH.sub.3 H SPh NL-15 H -- H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-15 H -- H OCH.sub.3 SPh SPh CHL-15 CH.sub.3 -- H OCH.sub.3 H SeCH.sub.3 CHL-15 CH.sub.3 -- H OCH.sub.3 H SePh CHL-15 CH.sub.3 -- H OCH.sub.3 H SPh CHL-15 CH.sub.3 -- H CH.sub.3 H SeCH.sub.3 CHL-15 CH.sub.3 -- H CH.sub.3 H SO.sub.2 Ph NL-15 CH.sub.3 -- H OCH.sub.3 SPh SPh CHL-15 CH.sub.2 CH.sub.3 -- H OCH.sub.3 H SeCH.sub.3 CHL-15 CH.sub.2 CH.sub.3 -- H OCH.sub.3 H SPh CHL-15 CH.sub.2 CH.sub.3 -- H CH.sub.3 H OPh CHL-15 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3 H SPh CHL-15 CH.sub.3 -- CH.sub.3 OCH.sub.3 H SePh CHL-15 H -- H OCH.sub.2 CH.sub.3 H SPh CHL-15 H -- H F H SPh CHL-15 H -- H Br H SeCH.sub.3 CHL-15 H -- H CF.sub.3 H SPh CHL-15 H -- H OCHF.sub.2 H SeCH.sub.3 CHL-15 H -- CH.sub.3 OCH.sub.3 SPh SPh NL-16 H -- H OCH.sub.3 H SeCH.sub.3 CHL-16 H -- H OCH.sub.3 H SePH CHL-16 H -- H OCH.sub.3 H SPh CHL-16 H -- H OCH.sub. 3 H OPh CHL-16 H -- H CH.sub.3 H SPh CHL-16 H -- H OCH.sub.3 H SPh NL-16 H -- H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-16 H -- H OCH.sub.3 SPh SPh CHL-16 CH.sub.3 -- H OCH.sub.3 H SeCH.sub.3 CHL-16 CH.sub.3 -- H OCH.sub.3 H SePh CHL-16 CH.sub.3 -- H OCH.sub.3 H SPh CHL-16 CH.sub.3 -- H CH.sub.3 H SeCH.sub.3 CHL-16 CH.sub.3 -- H CH.sub.3 H SO.sub.2 Ph NL-16 CH.sub.3 -- H OCH.sub.3 SPh SPh CHL-16 CH.sub.2 CH.sub.3 -- H OCH.sub.3 H SeCH.sub.3 CHL-16 CH.sub.2 CH.sub.3 -- H OCH.sub.3 H SPh CHL-16 CH.sub.2 CH.sub.3 -- H CH.sub.3 H OPh CHL-16 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3 H SPh CHL-16 CH.sub.3 -- CH.sub.3 OCH.sub.3 H SePh CHL-16 H -- H OCH.sub.2 CH.sub.3 H SPh CHL-16 H -- H F H SPh CHL-16 H -- H Br H SeCH.sub.3 CHL-16 H -- H CF.sub.3 H SPh CHL-16 H -- H OCHF.sub.2 H SeCH.sub.3 CHL-16 H -- CH.sub.3 OCH.sub.3 SPh SPh NL-17 H H H OCH.sub.3 H SeCH.sub.3 CHL-17 H H H OCH.sub.3 H SePh CHL-17 H H H OCH.sub.3 H SPh CHL-17 H H H OCH.sub.3 H OPh CHL-17 H H H CH.sub.3 H SPh CHL-17 CH.sub.3 H H OCH.sub.3 H SPh NL-17 CH.sub.3 H H OCH.sub.3 SeCH.sub.3 SeCH.sub.3 CHL-17 CH.sub.3 H H OCH.sub.3 SPh SPh CHL-17 H CH.sub.3 H OCH.sub.3 H SeCH.sub.3 CHL-17 H CH.sub.3 H OCH.sub.3 H SePh CHL-17 H CH.sub.3 H OCH.sub.3 H SPh CHL-17 H CH.sub.3 H CH.sub.3 H SeCH.sub.3 CHL-17 H CH.sub.3 H CH.sub.3 H SO.sub.2 Ph NL-17 CH.sub.3 CH.sub.3 H OCH.sub.3 SPh SPh CHL-17 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 H SePh CHL-17 CH.sub.3 H H OCH.sub.2 CH.sub.3 H SPh CHL-17 CH.sub.3 H H F H SPh CHL-17 CH.sub.3 H H Br H SeCH.sub.3 CHL-17 CH.sub.3 H H CF.sub.3 H SPh CHL-17 CH.sub.3 H H OCHF.sub.2 H SeCH.sub.3 CHL-17 CH.sub.3 H CH.sub.3 OCH.sub.3 SPh SPh NL-15 CH.sub.3 -- CH.sub.3 OCH.sub.3 H CH.sub.2 OH CHL-16 CH.sub.3 -- CH.sub.3 OCH.sub.3 H CH.sub.2 OH NL-17 CH.sub.3 H CH.sub.3 OCH.sub.3 H CH.sub.2 OH N__________________________________________________________________________ TABLE 10b______________________________________ ##STR88##L R.sub.13 R.sub.14 R X.sub.1 m.p. (.degree.C.)______________________________________L-15 H -- H CH.sub.3L-15 H -- H OCH.sub.3L-15 H -- H OCH.sub.2 CH.sub.3L-15 CH.sub.3 -- H CH.sub.3L-15 CH.sub.3 -- H OCH.sub.3L-15 CH.sub.3 -- H OCH.sub.2 CH.sub.3L-15 CH.sub.2 CH.sub.3 -- H CH.sub.3L-15 CH.sub.2 CH.sub.3 -- H OCH.sub.3L-15 CH.sub.2 CH.sub.3 -- H OCH.sub.2 CH.sub.3L-15 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3L-15 CH.sub.3 -- CH.sub.3 OCH.sub.3L-15 H -- CH.sub.3 OCH.sub.3L-16 H -- H CH.sub.3L-16 H -- H OCH.sub.3L-16 H -- H OCH.sub.2 CH.sub.3L-16 CH.sub.3 -- H CH.sub.3L-16 CH.sub.3 -- H OCH.sub.3L-16 CH.sub.3 -- H OCH.sub.2 CH.sub.3L-16 CH.sub.2 CH.sub.3 -- H CH.sub.3L-16 CH.sub.2 CH.sub.3 -- H OCH.sub.3L-16 CH.sub.2 CH.sub.3 -- H OCH.sub.2 CH.sub.3L-16 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3L-16 CH.sub.3 -- CH.sub.3 OCH.sub.3L-16 H -- CH.sub.3 OCH.sub.3L-17 H H H CH.sub.3L-17 H H H OCH.sub.3L-17 H H H OCH.sub.2 CH.sub.3L-17 CH.sub.3 CH.sub.3 H CH.sub.3L-17 CH.sub.3 CH.sub.3 H OCH.sub.3L-17 CH.sub.3 CH.sub.3 H OCH.sub.2 CH.sub.3L-17 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3L-17 CH.sub.3 H CH.sub.3 OCH.sub.3______________________________________ TABLE 10c______________________________________ ##STR89##L R.sub.13 R.sub.14 R m.p. (.degree.C.)______________________________________L-15 H -- HL-15 CH.sub.3 -- HL-15 CH.sub.2 CH.sub.3 -- HL-15 CH.sub.2 CH.sub.2 CH.sub.3 -- HL-15 CH.sub.3 -- CH.sub.3L-16 H -- HL-16 CH.sub.3 -- HL-16 CH.sub.2 CH.sub.3 -- HL-16 CH.sub.2 CH.sub.2 CH.sub.3 -- HL-16 CH.sub.3 -- CH.sub.3L-17 H H HL-17 H CH.sub.3 HL-17 H CH.sub.2 CH.sub.3 HL-17 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 HL-17 CH.sub.3 CH.sub.3 CH.sub.3______________________________________ TABLE 10d______________________________________ ##STR90## m.p.L R.sub.13 R.sub.14 R X.sub.1 E Z (.degree.C.)______________________________________L-15 H -- H OCH.sub.3 Cl CHL-15 H -- H OCH.sub.3 Br CHL-15 H -- H OCH.sub.3 Cl NL-15 H -- H CH.sub.3 Cl CHL-15 H -- H OCH.sub.2 CH.sub.3 Cl CHL-15 CH.sub.3 -- H OCH.sub.3 Cl CHL-15 CH.sub.3 -- H OCH.sub.3 Br CHL-15 CH.sub.3 -- H CH.sub.3 Cl CHL-15 CH.sub.3 -- H CH.sub.3 Cl NL-15 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Cl CHL-15 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Br CHL-15 CH.sub.2 CH.sub. 3 -- H OCH.sub.3 Cl NL-15 CH.sub.2 CH.sub.3 -- H CH.sub.3 Cl CHL-15 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Cl CHL-15 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Cl NL-15 H -- CH.sub.3 OCH.sub.3 Cl CHL-15 CH.sub.3 -- CH.sub.3 OCH.sub.3 Br CHL-16 H -- H OCH.sub.3 Cl CHL-16 H -- H OCH.sub.3 Br CHL-16 H -- H OCH.sub.3 Cl NL-16 H -- H CH.sub.3 Cl CHL-16 H -- H OCH.sub.2 CH.sub.3 Cl CHL-16 CH.sub.3 -- H OCH.sub.3 Cl CHL-16 CH.sub.3 -- H OCH.sub.3 Br CHL-16 CH.sub.3 -- H CH.sub.3 Cl CHL-16 CH.sub.3 -- H CH.sub.3 Cl NL-16 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Cl CHL-16 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Br CHL-16 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Cl NL-16 CH.sub.2 CH.sub.3 -- H CH.sub.3 Cl CHL-16 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Cl CHL-16 CH.sub.2 CH.sub.2 CH.sub.3 -- H OCH.sub.3 Cl NL-16 H -- CH.sub.3 OCH.sub.3 Cl CHL-16 CH.sub.3 -- CH.sub.3 OCH.sub.3 Br CH______________________________________ TABLE 10e__________________________________________________________________________ ##STR91##L R.sub.13 R.sub.14 R X Z G m.p. (.degree.C.)__________________________________________________________________________L-15 H -- H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-15 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH CH(OCH.sub.3).sub.2L-15 H -- H CH.sub.3 CH CH(OCH.sub.3).sub.2L-15 C.sub.3 H.sub.7 -n -- H OCH.sub.3 N CH(OCH.sub.3).sub.2L-16 H -- H OCH.sub.3 CH CH(OCH.sub.3).sub.2L-16 CH.sub.3 -- H OCH.sub.3 CH C.sub.6 H.sub.5L-17 H H H OCH.sub.3 CH CH(OCH.sub.2 CH.sub.2 O)L-17 CH.sub.3 CH.sub.3 H OCH.sub.3 CH CH(OCH.sub.3).sub.2L-15 H -- H OCH.sub.3 CH C.sub.6 H.sub.5__________________________________________________________________________

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few points to several hundred gallons per acre. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

______________________________________ Active Percent by Weight Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 5-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 1-95 5-99 0-15High Strength 90-99 0-10 0-2Compositions______________________________________

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4th Edn., McGraw-Hill, N.Y., 1963, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 14

______________________________________Wettable Powder______________________________________2-[[[4-methoxy-6-(phenoxymethyl)pyrimidin-2-yl]amino- 50%carbonyl]aminosulfonyl]benzoic acid, methylestersodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 43%The ingredients are blended and hammer-milled.______________________________________

EXAMPLE 15

______________________________________High Strength Concentrate______________________________________2-[[[4-methoxy-6-(phenoxymethyl)pyrimidin-2-yl]amino- 98.5%carbonyl]aminosulfonyl]benzoic acid, methylestersilica aerogel 0.5%synthetic amorphous fine silica 1.0%______________________________________

The ingredients are blended and ground in a hammer-mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). This material may be formulated in a variety of ways.

EXAMPLE 16

______________________________________Dust______________________________________Wettable powder of Example 14 10%pyrophyllite (powder) 90%______________________________________

The wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged. The product is suitable for use as a dust.

EXAMPLE 17

______________________________________Aqueous Suspension______________________________________2-[[[bis(4,6-trifluoromethyl)pyrimidin-2-yl]amino- 25%carbonyl]aminosulfonyl]benzoic acid, methylesterhydrated attapulgite 3%crude calcium ligninsulfonate 10%water 62%______________________________________

The ingredients are ground together in a ball, sand or roller mill until the solid particles have been reduced to diameters under 10 microns.

EXAMPLE 18

______________________________________Solution______________________________________2-[[[4-methoxy-6-(methylselenylmethyl)pyrimidin-2-yl]- 30%aminocarbonyl]aminosulfonyl]benzoic acid, methylesterdimethylformamide 70%______________________________________

The ingredients are combined and stirred to produce a solution, which can be used for low volume applications.

EXAMPLE 19

______________________________________Granule______________________________________Wettable Powder of Example 14 50%sugar 50%______________________________________

The ingredients are blended in a rotating or fluid bed mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm (U.S.S. #18 to 40 sieves), the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain 25% active ingredient.

UTILITY

Test results indicate that the compounds of the present invention are active herbicides. They should have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Alternatively, many of the subject compounds should be useful for the selective pre- or post-emergence weed control in crops, such as wheat and cotton.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.001 to 5 kg/ha, the lower rates being suggested for use on ligher soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types. They may also be used in combination with mefluidide.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

Although some of the compounds do not exhibit a high degree of activity at the low rates tested, it is expected that these compounds will exhibit herbicidal effects at higher rates.

TEST A

Seeds of crabgrass (Digitaris sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, cotton, sugar beet, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted and treated pre-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

B=burn; C=chlorosis or necrosis; E=emergence inhibition; G=growth retardation; H=formative effects; and U=unusual pigmentation. ##STR92## TABLE A Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8 Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Cmpd. 13 Cmpd. 14 Cmpd. 15 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory 9C 2C,4H 4C,8H 0 5C,9G 6C,9G 2C,2H 4 C,9H 2C,4H 9C 2C,7G 3C,7G 2C,4H 1C 0 Cocklebur 9C 1C,2G 4C,9H 0 5C,9H 6C,9H 1C 5C,9H 1C 9C 2C,8H 2C,5G 5G 1C,7G 0 Sicklepod 2C,4G 1C 3C,3H 0 2C,3H 5C,6G 0 3C,3H 1C 4C,8G 3G 2G 1C 2C,5G 5G Nutsedge 1C 0 2C,8G 0 3C,9G 6C,9G 0 3C,8G 0 10C 9G 0 2C,8G 2C,5G 2G Crabgrass 1C 0 2C,7G 0 3H 5G 0 4G 0 6C,9G 3G 2G 1C,3H 9C 0 Barnyardgrass 3C,8H 0 9C 0 9C 9C 1H 1H 0 9C 3C,9H 3C,8H 2C,8H 9C 4C,9H Wild Oats 2C,4G 0 6C,9H 0 4C,8G 5C,9G 0 5C,9G 0 9C 3C,5G 0 1C 4C,8G 0 Wheat 3C,8G 0 5C,9G 0 5C,9G 9C 0 6C,9G 0 9C 0 3G 1C 3C,9G 0 Corn 2C,9H 0 2C,9H 0 6C,9H 5C,9G 0 4C,9H 0 5U,9C 3C,9G 0 5C,9G 3C,9G 0 Soybean 3C,9G 4G 3C,8H 0 4C,9G 4C,9G 0 4C,9G 1C 9C 3C,7H 2H 1C 2C,9G 1H Rice 4C,9G 3G 4C,9G 0 6C,9G 5C,9G 0 5C,9G 0 9C 4C,9G 2C,7G 4G 5C,9G 2C,7G Sorghum 2C,9G 2G 4C,9G 0 4C,9G 6C,9G 2C,5G 4C,9G 1C 9C 2C,9G 3C,9H 2C,9G 4C,9G 2C,8G Sugar beet 9C 2C,7G 4C,8H 0 9C 9C 3C,7G 9C 2G 9C 2C,5H 4G 2C,3H 1C,4G 1C Cotton 3C,9H 0 4C,9H 0 2C,8H 4C,9H 2C,5G 3C,7H 0 10C 2C,3H 5G 1C,5G 5C,9G 1C Cmpd. 16 Cmpd. 17 Cmpd. 18 Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. 22 Compound 23 Cmpd. 24 Cmpd. 25 Cmpd. 26 Cmpd. 27 Cmpd. 28 Cmpd. 29 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.4 0.05 0.05 0.05 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory 2C,5G 0 0 0 2C,6G 2C,5H 3G 2C,3H 1C 1C 2C,7G 3C,3H 10C 2C,7G 2G Cocklebur 2C,6G 0 1C 2H 10C 9C 7H 5C,9G 6H 10C 10C 9C 10C 9C 2C,8G Sicklepod 0 0 0 0 3C,9G 3C,8G 2C,8G 0 1C 2C 2C,3G 3G 5C,9G 5C,9G 2C Nutsedge 0 0 0 0 3C,7G 8G 2C,9G 6G 0 0 5G 5G 2C,8G 9G 4G Crabgrass 2G 2G 2G 4G 5G 3C,6G 2C,5G 6G 2G 5G 2C,8G 2C,5G 3C,8G 2C,4G 0 Barnyardgrass 2C,7H 3H 3C,8H 4C,8H 3C,9H 5C,9H 5C,9H 2C,8H 4H 3C,9H 5C,9H 5C,9H 5C,9H 5C,9H 3C,9H Wild Oats 1C 0 0 0 2C,9G 2C,9G 3C,9G 0 0 2C,8G 2C,9G 2C,6G 3C,9G 2C,6G 0 Wheat 8G 3G 0 0 7G 9C 9G 0 0 6G 2C,9G 2C,8G 6G 5G 0 Corn 1C,1H 2C,3H 2C,6H 1C 9G 3C,9H 9G 2H 0 5U,9G 5U,9C 3C,9H 3C,9G 3C,9G 4C,9H Soybean 2C,2H 4G 2C,5H 1C 3C,8G 3C,8G 4C,9G 1C,3G 1H 2C,8G 9C 9C 5C,9G 4C,9G 3C,7H Rice 2C,8G 2C,8G 3C,9G 2C,7G 5C,9G 5C,9G 5C,9G 3C,5G 2C,3G 5C,9G 9C 5C,9G 5C,9G 3C,9G 2C,8G Sorghum 2C,7G 3C,7G 2C,8G 2C,7G 2C,9G 2C,9H 1U,9G 8H 5G 4C,9G 9C 2C,9G 3C,9G 4C,9G 3C,9H Sugar beet 2C 0 2H 1C 4C,9G 2C,5G 3G 3C,8H 2C,5G 3C,8H 5C,9G 3C,6H 9C 9C 9C Cotton 2C,3H 0 1C 1C 3C,6G 4C,8G 3C,8H 2G 2G 3C,8H 10C 2C,9G 5C,9G 3C,8G 4C,6G Cmpd. 30 Cmpd. 31 Cmpd. 32 Cmpd. 33 Cmpd. 34 Cmpd. 35 Cmpd. 36 Cmpd. 37 Cmpd. 38 Cmpd. 39 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 POST-EMERGENCE Morningglory 3C,8H 9C 3C,7H 2C,5G 3G 4C,9G 2C,6G 10C 5C,9G 9C Cocklebur 9C 9C 5C,9G 3C,9H 8G 9C 9H 9C 9C 5C,9G Sicklepod 2C,2H 4C,8G 2C,4G 2C,5G 1C 9C 8H 9C 9C 5C,9G Nutsedge 2C,6G 9G 5G 3G 3G 10C 5G 10C 9C 9G Crabgrass 2C,5G 2C,7G 5G 3G 2G 3C,7G 4G 6G 2G 3C,9G Barnyardgrass 3C,9H 5C,9H 9H 9H 3C,9H 5C,9G 9H 9C 5C,9H 9C Wild Oats 2C,5G 4C,8G 0 0 0 4C,9G 3G 9C 2C,5G 6C,9G Wheat 5G 7G 0 0 0 4C,9G 3G 4C,9G 2C,6G 6C,9G Corn 2C,9H 2C,8G 2C,9H 3C,9H 3C,8H 4C,9G 2C,9G 5C,9G 9G 3U,9G Soybean 4C,9G 3C,9G 4C,9G 5C,9G 3C,9G 9C 2C,8G 9C 4C,9G 5C,9G Rice 4C,9G 5C,9G 4C,9G 3C,8G 2C,7G 5C,9G 4C,9G 9C 5C,9G 6C,9G Sorghum 3C,9H 5C,9G 2C,9G 4C,9G 2C,7G 9C 3C,9G 9C 2C,9G 5C,9H Sugar beet 3C,7H 9C 9C 4C,9G 3C,8G 9C 9C 9C 9C 5C,9G Cotton 3C,6G 4C,8G 3C,8H 3G 2G 9C 3C,8G 9C 5C,9G 9C Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8 Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Cmpd. 13 Cmpd. 14 Cmpd. 15 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 PRE-EMERGENCE Morningglory 2C,8H 0 1C 0 4C,9G 9G 1C 3C,8H 0 9H 8 H 7H 6G 2C,7H 0 Cocklebur 2C,8H 0 0 0 3C,8H 8H 1H 1C 0 3C,9H 9H 8G 9H 8H -- Sicklepod 0 0 0 0 3C 3C 0 1C 0 5C,9G 5G 0 2G 2C,7G -- Nutsedge 1C 0 0 0 3C,8G 3C,9G 0 3C,5G 0 10E 8G 0 0 2C,5G 0 Crabgrass 0 0 0 0 0 3G 0 1C 0 5C,9G 0 0 0 2C,8H 0 Barnyardgrass 2H 0 0 0 5C,9H 5C,9H 0 2C,4H 0 5C,9H 3C,3H 0 2C,3H 4C,8H 2C Wild Oats 2C 0 0 0 3C,6G 5C,9G 0 3C,8H 0 6C,9H 2C,8G 2C,7G 2C,7G 4C,9G 1C Wheat 2G 0 0 0 3C,9H 2C,9H 0 2G 0 10E 2C,8G 0 2C,5G 4C,9H 2G Corn 2C,8H 0 2C,9H 0 3C,9H 3C,9H 0 3C,9H 0 10E 9G 5G 3C,9H 9H 4G Soybean 1H 0 0 0 3C,8H 2C,5H 0 3C,3H 0 9H 4C,6H 0 2C,6H 2C,2H 0 Rice 0 0 3G 0 9H 10E 0 3C,7G 0 10E 5C,9H 8G 3C,7H 10H 0 Sorghum 3C,9H 0 2C,9H 0 5C,9H 5C,9H 2C,5G 3C,9H 0 10H 9H 6H 3C,9H 9C 2C,4G Sugar beet 5C,9G 2H 5C,9G 0 5C,9G 9C 2G 9C 0 10E 4C,8G 6G 8G 9G 0 Cotton 5G 0 1C 0 2C,5G 2C,9G 0 3C,7G 0 9G 8G 3G 6G 8G 0 Cmpd. 16 Cmpd. 17 Cmpd. 18 Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. 22 Compound 23 Cmpd. 24 Cmpd. 25 Cmpd. 26 Cmpd. 27 Cmpd. 28 Cmpd. 29 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.4 0.05 0.05 0.05 0.05 0.05 0.05 0.05 PRE-EMERGENCE Morningglory 0 0 0 0 9G 8G 5G 2G 2H -- 6H 0 9G 8G 3C,9G Cocklebur -- 0 -- 0 8G 7H 8G 2H 6G 8H 9H 6H 8G 9G -- Sicklepod 0 0 0 0 7G 0 8G 2G 0 5G 5G 0 9G 8G 9G Nutsedge 0 0 0 0 8G 4G 10E 2G 0 7G 5G 0 9G 8G 5G Crabgrass 0 0 0 0 6G 6G 5G 0 0 5G 5G 2G 7G 2G 2G Barnyardgrass 1C 0 1C 2C 6H 8G 6G 3C,3H 1C 2C,8G 5C,9H 2C,8H 9H 9G 8G Wild Oats 2G 0 1C 1C 7G 3C,7G 5G 2G 0 2C,8G 8G 2C,8G 2C,8G 2C,8G 7G Wheat 7G 0 2G 3G 7G 2C,9H 4G 0 0 2C,8G 8G 6G 3C,9G 2C,8G 6G Corn 2C,3G 2G 2C,6G 1H 2C,8G 2C,8H 2C,8G 3G 1C 3C,9G 2C,9G 3C,7G 3C,9G 8G 2C,8G Soybean 0 0 1C 0 2H 0 0 0 0 2H 5H 3H 3C,6H 2C,4H 3C,5H Rice 0 0 0 1C 10E 10E 9H 6G 0 2C,9H 3C,8H 2C,8G 9H 9H 2C,8G Sorghum 2C,6G 3C,5G 2C,5G 3C,7G 4C,9H 2C,9G 2C,8G 8G 3G 2C,9H 5C,9H 2C,9G 3C,9G 2C,8G 3C,8H Sugar beet 4G 2H 2H 2H 5G 7G 3G 8G 3H 2C,8G 10E 3C,8G 4C,9G 3C,9G 3C,8G Cotton 0 0 0 0 5G 2G 7G 4G 0 7G 9G 2G 9G 8G 8G Cmpd. 30 Cmpd. 31 Cmpd. 32 Cmpd. 33 Cmpd. 34 Cmpd. 35 Cmpd. 36 Cmpd. 37 Cmpd. 38 Cmpd. 39 Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 PRE-EMERGENCE Morningglory 2G 9G 9G 0 3G 9G 8G 9G 7G 9G Cocklebur -- 9H 9H 9H -- -- -- 9H 7G 9H Sicklepod 6G 8G 8G 0 0 9G 9G 9C 7G 9G Nutsedge 4G 5G 0 0 0 10E 0 10E 10E 10E Crabgrass 2G 4G 2G 0 0 8G 0 3C,8G 0 4C,9G Barnyardgrass 3C,8G 8G 8G 2H 0 5C,9H 2C,8H 5C,9H 1C 3C,9H Wild Oats 2C,7G 2C,7G 2C,8G 0 0 5C,9G 7G 6C,9G 5G 4C,9G Wheat 7G 5C,9G 7G 0 0 10E 8G 6C,9H 4G 5C,9H Corn 8G 2C,8G 8G 0 0 10H 3C,9G 4C,9G 4G 9G Soybean 2C,2H 3C,6G 4C,5H 0 1H 9H 3C,8H 9G 2G 9H Rice 4C,9H 8G 7G 0 0 10E 8H 10E 9H 10E Sorghum 2C,8G 2C,9G 2C,9G 0 0 5C,9H 3C,9G 7C,9H 4G 5C,9G Sugar beet 2C,7G 3C,8G 9C 5G 2G 9C 9G 6C,9G 5G 5C,9G Cotton 6G 8G 8G 0 -- 9G 9C 9G 8G 9G

TEST B

Post-emergence

Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass (Alopecurus myosuroides), sugarbeets, nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), and giant foxtail (Setaria faberii). The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats (Avena fatua), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), Johnsongrass (Sorghum halepense) and barnyardgrass (Echinochloa crusgalli). The plants were grown for approximately fourteen days, then sprayed post-emergence with the chemicals dissolved in a non-phytotoxic solvent.

Post-emergence

Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass, sugarbeets, nutsedge, crabgrass, sicklepod, teaweed, jimsonweed, velvetleaf and giant foxtail. The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats, cocklebur, morningglory, johnsongrass and barnyardgrass. The two pans were sprayed pre-emergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and visually rated for plant response. The rating system was as described for Test A.

The data show that several of the compounds tested have utility for selective weed control in crops such as wheat and cotton.

TABLE B__________________________________________________________________________ Compound Compound 1 Compound 3 Compound 5 Compound 6 Compound 10Rate g/ha 250 62 16 4 62 16 4 250 62 16 4 250 62 16 4 62 16 4 62 16__________________________________________________________________________Post-EmergenceCorn 9G 7G 4G 2G 8G 5G 0 10C 10C 9G 5G 10C 10C 10G 5G 9G 3G 0 10G 10CWheat 0 0 0 0 9G 5G 0 10C 9C 3G 0 10C 10G 6G 0 6G 4G 0 10C 10CRice 5G 2G 0 0 9G 6G 4G 10C 10G 6G 0 10C 10C 10C 7G 8G 3G 0 10C 10CSoybeans 10G 9G 9G 7G 9G 8G 3G 10G 10G 10G 6G 10G 10G 10G 5G 9G 8G 4G 10G 10GCotton 10C 10C 10C 10G 6G 0 0 6G 3G 0 0 10G 10G 9G 5G 5G 0 0 10C 10GSugar beets 10C 10C 10C 10C 10G 9G 3G 10C 10C 10C 5G 10C 10C 10C 8G 10C 8G 3G 10C 10GCrabgrass 5G 2G 0 0 8G 4G 2G 7G 2G 0 0 10C 8G 4G 0 0 0 0 10C 9GJohnsongrass 7G 6G 3G 0 9G 8G 2G 10C 10C 0 0 10C 10C 6G 3G 10G 10G 4G 10C 10CBlackgrass 8G 6G 4G 0 8G 5G 0 10C 10C 0 0 10C 10C 10G 5G 4G 0 0 10C 10CBarnyardgrass 2G 0 0 0 9G 4G 0 10C 10C 9G 3G 10C 10C 7G 2G 0 0 0 10G 10CNutsedge 10C 10C 9C 6C 8G 4G 0 9C 9C 4G 0 10C 10C 9C 3G 0 0 0 10C 9CGiant foxtail -- -- -- -- -- -- -- 10C 10C 7G 4G 10C 7G 5G 2G 3G 0 0 10C 10GWild Oats 0 0 0 0 9G 2G 0 9C 5G 0 0 10C 9G 6G 0 9G 5G 0 10C 10CCocklebur 10C 10C 10C 10G 10G 3G 0 10C 10G 10G 7G 10G 10G 9G 8G 9G 8G 2G 10G 10GMorningglory 10C 10C 10C 10C 7G 4G 2C 10C 10G 8G 3G 10G 10G 9G 6G 8G 6G 0 10G 9GTeaweed 10G 10G 10G 6G 10G 4G 0 5G 0 0 0 10G 6G 4G 0 3G 0 0 10G 7GSicklepod 10G 10G 10G 7G 7G 2G 0 6G 2G 0 0 10G 7G 3G 3G 3G 0 0 10G 10GJimsonweed 10C 10C 10G 7G 10G 7G 5G 10G 10G 5G 3G 10C 10G 10G 7G 9G 6G 2G 9G 5GVelvetleaf 10C 10C 10C 9G 6G 3G 0 3G 0 0 0 10C 10G 8G 4G 4G 0 0 10C 8G__________________________________________________________________________ Compound 10 Compound 14 Compound 24 Compound 37 Rate g/ha 4 1 250 62 16 4 250 62 16 4 62 16 4 1__________________________________________________________________________ Post-Emergence Corn 7G 4G 10B 10G 4G 0 10C 10C 9G 7G 10C 10G 10C 5G Wheat 6G 0 5G 0 0 0 0 0 0 0 7G 3G 0 0 Rice 10G 10C 9B 8G 7G 3G 10G 9G 8G 4G 10G 9G 6G 2G Soybeans 8G 3G 10G 8G 3G 0 9G 7G 3G 0 10G 10G 10G 6G Cotton 6G 2G 9G 8H 2G 0 7G 4G 0 0 10G 10G 5G 2G Sugar beets 8G 5G 9B 4G 2G 0 9G 8G 4G 0 10C 10C 10C 10C Crabgrass 5G 3G 10B 3G 0 0 2G 0 0 0 8G 4G 2G 0 Johnsongrass 10C 4G 10B 8B 3G 0 8G 3G 0 0 10C 10C 6G 3G Blackgrass 9G 8G 9B 9B 3G 0 6G 2G 0 0 10C 9G 4G 2G Barnyardgrass 10C 4G 9B 8B 4G 2G 7G 7G 7G 5G 10C 10C 5G 2G Nutsedge 5G 0 5G 2G 0 0 0 0 0 0 10C 10C 9G 4G Giant foxtail 4G 0 9B 6G 2G 0 9G 7G 2G 0 10G 7G 3G 0 Wild Oats 6G 4G 4G 0 0 0 0 0 0 0 8G 2G 0 0 Cocklebur 8G 3G 8G 4G 2G 0 9G 9G 9G 6G 9G 7G 2G 0 Morningglory 4G 0 9G 2C 0 0 2C 2G 0 0 10G 10G 9G 5G Teaweed 2G 0 2C 0 0 0 4G 2G 0 0 9G 6G 3G 0 Sicklepod 10G 5G 2G 0 0 0 2G 0 0 0 10C 9G 4G 0 Jimsonweed 2G 0 4G 2G 0 0 0 0 0 0 10G 9G 9G 7G Velvetleaf 7G 2G 8G 4G 2G 0 8G 6G 3G 0 10C 10C 8G 3G__________________________________________________________________________ Com- pound Compound 1 Compound 3 Compound 5 Compound 6 Compound 8 Compound 11Rate g/ha 250 62 62 16 250 62 16 250 62 16 4 62 16 62 16 4 1 250__________________________________________________________________________Pre-EmergenceCorn 7G 4G 0 0 10G 2G 0 10E 10G 3G 0 8G 2G 10G 10G 8G 2G 7GWheat 0 0 2G 0 9G 7G 3G 9G 7G 3G 0 0 0 10G 10G 5G 3G 5GRice 10G 7G 7G 3G 10E 10G 5G 10E 10E 10E 7G 8G 2G 10E 10E 10E 9G 8GSoybean 8G 4G 2C 0 9G 2G 0 8G 5G 2G 0 4G 0 9G 6G 4G 0 6GCotton 10G 7G 0 0 0 0 0 3G 2G 0 0 0 0 9G 4G 2G 0 2GSugar beets 10G 9G 7G 0 10G 10G 5G 10E 10E 10E 3G 9G 3G 10G 10G 8G 3G 9GCrabgrass 6G 3G 4G 0 10G 4G 0 9G 8G 5G 0 3G 0 10G 10G 5G 0 2GJohnsongrass 6G 5G 7G 4G 10G 8G 2G 10C 9G 8G 2G 9G 3G 10C 10G 9G 3G 7GBlackgrass 8G 6G 3G 2G 0 0 0 10E 10E 7G 3G 0 0 10E 10E 10G 5G 9GBarnyardgrass 4G 2G 4G 2G 10G 7G 4G 10G 10G 3G 0 4G 0 10G 10G 8G 2G 3GNutsedge 10E 8G 3G 0 8G 2G 0 10E 10E 5G 0 0 0 10E 10E 5G 0 8GGiant foxtail 10E 4G 8G 6G 9G 9G 3G 10E 10G 3G 0 0 0 10E 10G 10G 4G 2GWild Oats 0 0 3G 0 9G 5G 3G 10G 8G 5G 3G 3G 0 9G 8G 5G 3G 3GCocklebur 10G 8G 4G 0 6G 2G 0 10G 7G 2G 0 0 0 10G 9G 5G 0 2GMorningglory 10G 7G 0 0 3G 0 0 3G 4G 0 0 0 0 9G 6G 2G 0 3GTeaweed 9G 7G 5G 3G 6G 4G 0 10G 5G 0 0 2G 0 9G 5G 0 0 4GSicklepod 9G 6G 7G 4G 10E 3G 0 10E 6G 2G 0 3G 0 10E 10E 4G 0 0Jimsonweed 10G 9G 2G 0 8G 4G 0 10G 7G 3G 0 0 0 10G 8G 5G 0 8GVelvetleaf 10G 8G 0 0 7G 3G 0 10G 8G 3G 0 0 0 10G 10G 7G 0 5G__________________________________________________________________________ Compound 11 Compound 14 Compound Compound 37 Rate g/ha 62 16 250 62 16 4 250 62 62 16 4__________________________________________________________________________ Pre-Emergence Corn 2G 0 8G 5G 2C 0 6G 2G 8G 4G 0 Wheat 2G 0 6G 3G 0 0 2G 0 5G 3G 0 Rice 7G 5G 10G 10G 6G 2C 6G 4G 10G 9G 5G Soybean 2C 0 6C 4G 3G 2G 2G 0 10G 5G 2G Cotton 0 0 3C 0 0 0 3G 2G 8G 4G 0 Sugar beets 4G 2G 5G 2G 0 0 4G 2G 10G 4G 0 Crabgrass 0 0 9G 9G 3G 0 5G 3G 7G 2G 0 Johnsongrass 4G 2G 9G 5G 0 0 8G 4G 10G 8G 2G Blackgrass 5G 3G 9G 6G 3C 0 5G 2G 10G 8G 3G Barnyardgrass 0 0 9G 5G 0 0 5G 2G 9G 6G 2G Nutsedge 6G 2G 6G 3G 2C 0 4G 2G 9G 4G 2G Giant foxtail 0 0 9G 5G 0 0 6G 2G -- -- -- Wild Oats 0 0 5G 2G 0 0 4G 2G 3G 0 0 Cocklebur 0 0 6G 4G 2G 0 5G 2G 9G 2G 0 Morningglory 0 0 7C 3C 2G 0 4G 2G 5G 2G 0 Teaweed 2G 0 6G 3G 0 0 5G 3G 9G 3G 0 Sicklepod 0 0 5G 2G 0 0 2G 0 8G 4G 2G Jimsonweed 5G 2G 3G 2G 0 0 4G 2G 9G 2G 0 Velvetleaf 2G 0 7G 4G 2G 0 5G 3G 9G 6G 0__________________________________________________________________________

Claims

1. A compound of the formula: ##STR93## wherein R is H or CH.sub.3 ;

L is ##STR94## R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, F, Cl, Br, NO.sub.2, CF.sub.3, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.18, S(O).sub.n R.sub.19, WCF.sub.3, WCHF.sub.2, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.6 H.sub.5, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, ##STR95## R.sub.2 is H, F, Cl, Br, CF.sub.3, CH.sub.3, OCH.sub.3 or SCH.sub.3 ; R.sub.15 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.dbd.CH.sub.2 ;

R.sub.16 is C.sub.1 -C.sub.2 alkyl;

R.sub.17 is C.sub.1 -C.sub.2 alkyl;

R.sub.18 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ;

R.sub.19 is C.sub.1 -C.sub.3 alkyl or CH.sub.2 CH.dbd.CH.sub.2 ; and

W is O, S or SO.sub.2 ;

A is ##STR96## X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, F, Cl, Br, CF.sub.3 or OCHF.sub.2 ;

T is H, SeCH.sub.3, SeC.sub.6 H.sub.5, SCH.sub.3 or ##STR97## Y is SeCH.sub.3, SeO.sub.6 H.sub.5, ##STR98## OSi(CH.sub.3).sub.3, CH.sub.2 OH or CH.sub.2 OSi(CH.sub.3).sub.3 ; Z is CH;

R.sub.20 is H, CH.sub.3, CF.sub.3, OCH.sub.3, F, Cl, Br or NO.sub.2 ;

p is 0, 1 or 2; and

q is 0, 1 or 2;

provided that

the sum of p and q is less than or equal to 2;

and their agriculturally suitable salts.

2. A compound of claim 1 wherein R is H.

3. A compound of claim 2 wherein R.sub.2 is H, R.sub.20 is H, X is CH.sub.3 or OCH.sub.3, T is H, p is 0 and q is 0.

4. A compound of claim 3 wherein R.sub.1 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, NO.sub.2, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, OSO.sub.2 CH.sub.3 or WCHF.sub.2.

5. The compound of claim 1 which is 2-[[[4-methoxy-6-(phenoxymethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.

6. The compound of claim 1 which is 2-[[[4-methoxy-6-(methylselenylmethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.

7. The compound of claim 1 which is 2-[[[4-methoxy-6-(phenylthiomethyl)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.

8. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid inert diluent.

9. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid inert diluent.

10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid inert diluent.

11. A composition suitable for controlling the growth of undesired vegetation wich comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid inert diluent.

12. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.

13. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.

14. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.

15. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.