TREA

Herbicidal sulfonamides

Follow

Information

  • Patent Grant
  • 4822403
  • Patent Number
    4,822,403
  • Date Filed
    Friday, October 10, 1986
    38 years ago
  • Date Issued
    Tuesday, April 18, 1989
    35 years ago
Information
Abstract
The invention relates to certain sulfonamide compounds having substituents ortho to the sulfonylurea linkage, said substituents including alkenyl, substituted alkenyl, cycloalkenyl, substituted cycloalkenyl, alkynyl and substituted alkynyl.
Description

BACKGROUND OF THE INVENTION
The invention relates to certain sulfonamide compounds having alkenyl, cyclic alkenyl, alkynyl, substituted alkenyl, substituted cyclic alkenyl and substituted alkynyl substituents ortho to the sulfonylurea linkage, agriculturally suitable compositions thereof and method of their use as herbicides or plant growth regulants.
In the most common situation, the control of undesired vegetation is desired to permit the growth of useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 4,368,069 discloses herbicidal benzenesulfonamides of formula ##STR1## wherein
R is --(CR.sub.5 R.sub.6).sub.n --R.sub.2 ;
n is 0 or 1; and
R.sub.2 may be C.sub.5 -C.sub.6 cycloalkenyl or C.sub.2 -C.sub.5 alkenyl.
South African patent application No. 83/3779 discloses herbicidal sulfonamides of formula ##STR2## wherein A is a radical of the formula C.tbd.CR; and
R is, among others, a variety of alkyl or substituted alkyl groups.
Herbicidal thiophene sulfonamides are disclosed in European patent application (EP-A) No. 30,142, published June 10, 1981.
Herbicidal pyridinesulfonamides are disclosed in European patent application (EP-A) No. 13,480, published July 23, 1980.
U.S. Pat. No. 4,420,325 discloses herbicidal sulfonamides of the following formula ##STR3## wherein
R.sub.1 is F, Cl, Br, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkyl, NO.sub.2, CO.sub.2 R.sub.4, SO.sub.2 R.sub.5, SO.sub.2 NR.sub.6 R.sub.7, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 CH.sub.2 CF.sub.3, OSO.sub.2 R.sub.5 or CH.sub.2 L; and
R.sub.9 is H or C.sub.1 -C.sub.3 alkyl.
South African patent application No. 84/2722, published 10/13/84, discloses herbicidal sulfonamides of formula ##STR4## wherein
A is a radical of formula --CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
R.sub.6 is H, C.sub.1 -C.sub.4 alkyl or fluorine;
R.sub.7 is H or CH.sub.3 ;
X is O, S, SO or SO.sub.2 ;
R.sub.8 may be C.sub.2 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 alkynyl, etc.
South African patent application No. 84/6610 discloses herbicidal pyrazolesulfonylureas of formula ##STR5## wherein
X is O or NR.sub.6 ;
R.sub.1 and R.sub.2 are independently H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl, which are optionally substituted by 1-3 halogen atoms, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, OH, etc.
South African patent application No. 83/6449, published 3/1/84, discloses herbicidal sulfonylureas of the formula ##STR6## wherein
R.sub.3 is C.sub.2 -C.sub.10 alkenyl which is substituted by, inter alia, one or more fluorine or bromine atoms or by one or more hydroxyl, cyano or nitro groups.
European Publication No. 132,230, published 1/23/85, discloses a process for preparing sulfonylureas of the formula ##STR7## wherein
T denotes a substituted phenyl radical of formula ##STR8## X is, inter alia, H, halogen, C.sub.2 -C.sub.4 alkynyl; R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; and ##STR9##
SUMMARY OF THE INVENTION
New compounds have been discovered which possess herbicidal activity as well as agriculturally suitable compositions thereof and a method of their use as general and/or selective preemergent and/or postemergent herbicides or plant growth regulants. Accordingly the compounds of the invention possessing herbicidal activity are compounds of the formula ##STR10##
R is H or CH.sub.3 ;
W.sub.3 is O or S;
n is O or 1;
E is S(O).sub.p or Se;
p is 0, 1 or 2;
R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CN, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl or CO.sub.2 R.sup.III ;
R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy;
R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or
R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
R.sub.2 is C.sub.1 -C.sub.3 alkyl;
W is W.sub.1 or W.sub.2 ;
W.sub.1 is C.sub.2 -C.sub.8 alkenyl or C.sub.4 -C.sub.7 cycloalkenyl either of which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, amino, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, (C.sub.1 -C.sub.3 alkylamino)sulfamoyl, di(C.sub.1 -C.sub.3 alkylamino)sulfamoyl, OC(O)C.sub.1 -C.sub.3 alkyl, C(O)C.sub.1 -C.sub.3 alkoxy, OC(O)C.sub.1 -C.sub.3 alkoxy, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.6 H.sub.5, OSO.sub.2 --4--CH.sub.3 --C.sub.6 H.sub.4, phenyl or phenyl substituted with halogen, CH.sub.3, OCH.sub.3, SCH.sub.3 or NO.sub.2 ;
W.sub.2 is C.sub.2 alkynyl which may be substituted with phenyl or phenyl substituted with halogen, CH.sub.3, OCH.sub.3, SCH.sub.3 or NO.sub.2 or W.sub.2 is C.sub.3 -C.sub.8 alkynyl which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, (C.sub.1 -C.sub.3 alkylamino)sulfamoyl, di(C.sub.1 -C.sub.3 alkylamino)sulfamoyl, OC(O)C.sub.1 -C.sub.3 alkyl, OC(O)C.sub.1 -C.sub.3 alkoxy, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.6 H.sub.5, OSO.sub.2 --4--CH.sub.3 --C.sub.6 H.sub.4, phenyl or phenyl substituted with halogen, CH.sub.3, OCH.sub.3, SCH.sub.3 or NO.sub.2 ;
R.sub.3 is H or C.sub.1 -C.sub.4 alkyl; ##STR11## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino;
Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl,
C.sub.2 -C.sub.4 alkynyl, ##STR12## m is 2 or 3;
L.sub.1 and L.sub.2 are independently O or S;
R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl;
R.sub.6 is H or CH.sub.3 ;
Z is CH or N;
Y.sub.1 is O or CH.sub.2 ;
X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H;
Y.sub.2 is H or CH.sub.3 ;
X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ;
Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ;
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; and
X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or CH.sub.2 OCH.sub.3 ; and their agriculturally suitable salts; provided that
(a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
(b) when X or Y is OCF.sub.2 H then Z is CH;
(c) when L is L-2 or L-3, then the W substituent and the sulfonylurea bridge are on adjacent carbon atoms;
(d) when W.sub.1 is C.sub.3 alkenyl, then L is L-3, L-4, L-5 or L-6;
(e) when L is L-1, L then n is 1 and W is W.sub.2 ;
(f) when L is L-1 and W.sub.2 is C.sub.2 or C.sub.3 alkynyl, said group must be substituted;
(g) when W.sub.1 is C.sub.3 -C.sub.8 alkenyl or C.sub.4 -C.sub.7 cycloalkenyl substituted with OH, then the OH substituent is not bonded directly to the olefinic group;
(h) when L is L-3, then the sulfonylurea bridge is bonded at the 3- or 5-position;
(i) when W.sub.3 is S, then R is H, A is A-1, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3 or CH(OCH.sub.3).sub.2 ;
(j) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R.sub.1 must be less than or equal to two and the number of carbons of W must be less than or equal to four; and
(k) when L is L-2, L-3, L-4 or L-5, then W.sub.1 is other than C.sub.2 -C.sub.8 alkenyl substituted with 1-3 atoms of F, Cl or Br.
In the above definitions, the term "alkyl" used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.
Alkenyl denotes straight chain or branched alkenes, e.g., vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl, pentenyl, hexenyl, heptenyl and octenyl isomers.
Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl, hexynyl, heptynyl and octynyl isomers.
Cyclohexenyl means cyclobutenyl, cyclopentenyl, cyclohexenyl and cycloheptenyl.
The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine.
In terms such as C.sub.2 -C.sub.3 alkylthioalkyl, the specified number of carbon atoms is meant to define the total number of carbon atoms in that substituent group. For example, C.sub.2 -C.sub.3 alkylthioalkyl would designate CH.sub.2 SCH.sub.3, CH.sub.2 SC.sub.2 H.sub.5, CH.sub.2 CH.sub.2 SCH.sub.3 or CH(CH.sub.3)SCH.sub.3, and C.sub.2 -C.sub.5 alkoxyalkoxy would represent OCH.sub.2 OCH.sub.3 through O(CH.sub.2).sub.4 OCH.sub.3 or OCH.sub.2 O(CH.sub.2).sub.3 CH.sub.3 and the various structural isomers embraced therein.
Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the different propylsulfonyl isomers.
Alkylthio, alkylsulfinyl, alkylamino, alkylsulfamoyl, etc. are defined in an analogous manner.
The compounds of the invention which are preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:
(1) Compounds of Formula I where
R is H; and
W.sub.3 is O.
(2) Compounds of Preferred 1 where
R.sub.1 is H, F, Cl, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CH.sub.2 OCH.sub.3 or CH.sub.2 SCH.sub.3, and is not para to the sulfonylurea bridge.
(3) Compounds of Preferred 2 where
X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and
Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3.
(4) Compounds of Preferred 3 where
W.sub.1 is C.sub.2 -C.sub.5 alkenyl which may be optionally substituted by 1-3 atoms of F, Cl or Br, OH, OCH.sub.3, OC(O)CH.sub.3, OSO.sub.2 CH.sub.3, CN or SCH.sub.3, or W.sub.1 is C.sub.5 -C.sub.6 cycloalkenyl; and
W.sub.2 is C.tbd.CC.sub.6 H.sub.5 or C.sub.3 -C.sub.5 alkynyl which may be optionally substituted by 1-3 atoms of F, Cl or Br, OH, OCH.sub.3, OC(O)CH.sub.3, CN or SCH.sub.3.
(5) Compounds of Preferred 4 where
A is A-1;
X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl or OCF.sub.2 H;
Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2, OCF.sub.2 H, NHCH.sub.3, N(CH.sub.3).sub.2 or cyclopropyl; and
R.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl.
(6) Compounds of Preferred 5 where
L is L-1.
(7) Compounds of Preferred 5 where
L is L-2; and
W is W.sub.1.
(8) Compounds of Preferred 5 where
L is L-2; and
W is W.sub.2.
(9) Compounds of Preferred 5 where
L is L-3; and
W is W.sub.1.
(10) Compounds of Preferred 5 where
L is L-3; and
W is W.sub.2.
(11) Compounds of Preferred 5 where
L is L-4; and
W is W.sub.1.
(12) Compounds of Preferred 5 where
L is L-4; and
W is W.sub.2.
(13) Compounds of Preferred 5 where
L is L-5; and
W is W.sub.1.
(14) Compounds of Preferred 5 where
L is L-5; and
W is W.sub.2.
(15) Compounds of Preferred 5 where
L is L-6; and
W is W.sub.1.
(16) Compounds of Preferred 5 where
L is L-6; and
W is W.sub.2.
(17) Compounds of Preferred 5 where
L is L-7.
Compound specifically preferred for reasons of their expected greatest ease of synthesis and/or greatest herbicidal efficacy are:
2-(1-cyclohexen-2-yl)-N-[4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3-thiophenesulfonamide, m.p. 190.degree.-192.degree. C.;
2-(1-cyclohexen-2-yl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-3-thiophenesulfonamide, m.p. 169.degree.-171.degree. C.; and
N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(1-propenyl)-1H-pyrazole-5-sulfonamide, m.p. 155.degree.-158.degree. C.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The compounds of Formula I can be prepared by reacting an appropriate sulfonyl isocyanate or sulfonyl isothiocyanate, II, with an appropriately substituted aminoheterocycle, III, as shown in Equation 1, where R, W.sub.3, A and L are as previously defined. ##STR13##
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, where W.sub.3 is O, can 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.sup.III. ##STR14##
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'.dbd.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, as disclosed in European patent application (EP-A) No. 44,807. Compounds of Formula I can also be prepared from a phenyl carbamate V and the tert-butyldimethylsilane-protected sulfonamide IV (LSO.sub.2 NHSi(CH.sub.3).sub.2 -t-Bu). Addition of tetrabutylammonium fluoride to a mixture of the carbamate and sulfonamide affords, after workup, the desired product. The required carbamates can be prepared from the corresponding amines, III, and dimethyl- or diphenylcarbonate or methyl- or phenylchloroformate and a base such as sodium hydride.
The sulfonyl isocyanates, 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.
Sulfonyl isothiocyanates of Formula II, where W.sub.3 is S, can be prepared according to the method of K. Hartke, Arch. Pharm., 299, 174 (1966).
The intermediate sulfonamides IV used to prepare the corresponding sulfonylureas I can be prepared in a variety of ways. For example, 1 may be prepared from 2 via the lithiation, condensation protocol outlined in Equation 3. ##STR15##
This same methodology can also be applied to other sulfonamides such as thiophene 3 and pyrazole 4 as outlined in Equation 4. The examples depicted are meant to be exemplary and the methodology is applicable to a wide range of values for W and the various aromatic thiophene, pyrazole, pyridine and benzyl isomers. ##STR16##
Sulfonamides such as 1, 3 and 4 can also be prepared from the corresponding olefin or alkyne as outlined in Equation 5, where W is as previously defined. ##STR17##
Olefinic sulfonamides such as 5 can be prepared from the methyl-substituted t-butylsulfonamide 6, as outlined in Equation 6. Here again, the example is intended to be exemplary and would be applicable to a wide variety of values for R.sub.1 and W.sub.1. ##STR18##
The sulfonamides IV of the invention such as 8 or 9 can also be prepared via a modification of the Ullman reaction as outlined in Equation 7. ##STR19##
Intermediates such as 9 can also be used to prepare the corresponding olefins such as 8 via catalytic hydrogenation, employing a catalyst such as Lindlar catalyst.
Condensation of protected sulfonamides, for example 3c, with ketones and aldehydes followed by elimination also affords the desired sulfonamides. This is outlined in Equation 8. ##STR20##
Sulfonamides such as 3d can be prepared via the aldehyde 3e by a Knoevenagel type condensation with active methylene compounds as shown in Equation 9. Appropriate active methylene compounds include malonic esters, malononitrile, .alpha.-cyanoacetates, .alpha.-nitroacetates to name a few. ##STR21##
Similar condensation with pyrazole, pyridine or benzene aldehydes provides access to the corresponding difunctionalized alkenyl sulfonamides.
One skilled in the art will recognize that many of the methods described above can result in the formation of two possible geometrical isomers about the carbon-carbon double bond. This invention is meant to encompass all isomers. In cases where a mixture is obtained, the isomers can be separated by standard methods, such as fractional recrystallization or chromatography. Alternatively, the compounds can be used as a mixture of double bond isomers.
The intermediate pyrazole, thiophene, pyridine and benzyl sulfonamides are well known to one skilled in the art. For further information pertaining to their preparation see EP-A-95,925; EP-A-30,142; EP-A-13,480; EP-A-51,466; and U.S. Pat. No. 4,420,325. The lithiation of both aromatic and heterocyclic compounds is well known to one skilled in the art. For further information pertaining to this methodology see Stowell, J. C. "Carbanions in Organic Synthesis", John Wiley & Sons: New York, 1979; Snieckus, V. Tetrahedron Lett. 26, 1145 (1985) and ibid, 1149 (1985).
The heterocyclic amines of Formula III can be prepared by methods known in the literature or simple modifications thereof, by those skilled in the art. For instance, EP-A-84,224 (published July 27, 1983) and W. Braker et al, J. Am. Chem. Soc. 1947, 69, 3072 describe methods for preparing aminopyrimidines and triazines substituted by acetal groups. Also, South African Patent Application Nos. 825,045 and 825,671 describe methods for preparing aminopyrimidines and triazines substituted by haloalkyl or haloalkylthio groups such as OCH.sub.2 CH.sub.2 F, OCH.sub.2 CF.sub.3, SCF.sub.2 H, and OCF.sub.2 H among other groups. South African Patent Application No. 837,434 (published Oct. 5, 1983) describes methods for the synthesis of cyclopropylpyrimidines and triazines substituted by such groups as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, and alkoxyalkyl.
The 5,6-dihydrofuro[2.3-d]pyrimidin-2-amines, and the cyclopenta[d]pyrimidin-2-amines, of Formula III, where A is A-2, and the 6,7-dihydro-5H-pyrano-[2.3-d]pyrimidin-2-amines, of Formula III, where A is A-3, can be prepared as described in EP-A No. 15,863. The furo[2.3-d]pyrimidin-2-amines, of Formula III, where A is A-4, are described in EP-A No. 46,677. Heterocycles of formula III, where A is A-5, can be prepared as described in EP-A No. 73,562. Heterocycles of Formula III, where A is A-6, can be prepared by methods taught in EP-A-94,260. Compounds of Formula III, where A is A-7, can be prepared by methods taught in EP-A-125,864.
In addition, general methods for preparing aminopyrimidines and triazines have been reviewed in the following publications.
"The Chemistry of Heterocyclic Compounds", a series published by Interscience Publishers, Inc., New York an London;
"Pyrimidines", Vol. 16 of the same series by D. J. Brown;
"s-Triazines and Derivatives", Vol. 13 of the same series by E. M. Smolin and L. Rapaport; and
F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963), which describe the synthesis of triazines.
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 or carbonate). 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 contacting of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal 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, e.g., a copper salt, 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. In this method, the cation of the resin is 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, e.g., a potassium, sodium or calcium salt.
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 preparation of the compounds of this invention is illustrated by the following examples.
EXAMPLE 1
Preparation of 2-(1-Cyclohexenyl)-3-thiophenesulfonamide
A solution of 3-bromo-2-(1-cyclohexenyl)-thiophene (prepared by the method of N. Gjos and S. Gronowitz, Acta. Chem. Scan., 26, 1851-59, (1972)) (8.0 g, 32.9 mmol) in ether (30 ml) was added dropwise to a stirring solution of n-butyllithium (1.37M, 25.2 ml, 34.6 mmol) in ether (60 ml) precooled to -78.degree. C. The solution was stirred another 30 minutes at -78.degree. C. and was then treated with sulfuryl chloride (3.2 ml, 40 mmol) in hexane (10 ml). After an additional 30 minutes at -78.degree. C., anhydrous ammonia (9 ml, 300 mmol) was added, the suspension warmed to 25.degree. C. and poured into ether, washed with water and brine, dried over magnesium sulfate and reduced in volume. The product was crystallized by trituration with butyl chloride and hexane affording 2.51 g white solid (31%) m.p. 115.degree.-121.degree. C.
EXAMPLE 2
Preparation of 2-(1-Cyclohexen-2-yl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3-thiophenesulfonamide
To a stirring solution of 2-(1-cyclohexenyl)-3-thiophenesulfonamide (160 mg, 0.657 mmol), and 4-methyl-6-methoxy-2-aminophenoxycarbonyl pyrimidine (180 mg, 0.69 mmol) in 15 ml of acetonitrile was added 1,8-diazabicyclo[5.4.0]undec-7-ene (105 mg, 0.69 mmol). The reaction was stirred overnight, poured into water, acidified with acetic acid and extracted with methylene chloride, dried over magnesium sulfate and concentrated to yield the desired product, 170 mg, m.p. 190.degree.-192.degree. C.
NMR(.delta.) (d.sub.6 -DMSO) (200 MHz): 1.3-2.4 (m, with s at 2.10, 11H); 3.79 (s, 3H); 5.8-6.0 (m, 1H); 6.42 (s, 1H), 7.30 and 7.44 (AB q, J=5.4 Hz, 2H).
EXAMPLE 3
Preparation of 4-(1-Hydroxypropyl)-1-methyl-5-tert-butylpyrazolesulfonamide
To a cooled solution of n-butyl lithium (1.8 g, 27.9 mmol) in 150 ml of tetrahydrofuran was added 4-bromo-5-tert-butylsulfonamide-N-methylpyrazole. After stirring for 30 minutes at 0.degree.-78.degree. C., propionaldehyde (1.5 g, 27.9 mmole) was added dropwise. After standard workup, a red oil was isolated. Crystallization from ethyl acetate/hexane afforded 3.1 g of the desired compound, m.p. 113.degree.-115.degree. C.
EXAMPLE 4
Preparation of 4-(2-Propenyl)-1-methyl-5-pyrazole sulfonamide
The alcohol (3.0 g) from Example 3 was stirred in 25 ml of trifluoroacetic acid at 68.degree. C. for 30 minutes. The solution was allowed to cool to room temperature, and the volatile components were removed in vacuo to afford 510 mg of the desired sulfonamide, m.p. 157.degree.-161.degree. C.
EXAMPLE 5
Preparation of N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(1-propenyl)-1H-pyrazole-5-sulfonamide
The sulfonamide from Example 4 (150 mg, 0.7 mmol) and the phenylcarbamate of 4,6-dimethoxy-2-aminopyrimidine (202 mg, 0.7 mmol) were dissolved in 5 ml of acetonitrile. 1,8-Diazabicyclo[5.4.0]undec-7-ene (112 mg, 0.7 mmol) was added and the reaction was stirred for 30 minutes. Addition of 5 ml of 5% hydrochloric acid resulted in a solid, which was collected and dried to afford 280 mg of the desired product, m.p. 154.degree.-156.degree. C.
NMR (200 MHz, CDCl.sub.3 ): .delta. 1.84 (d, 3H); 3.56 (s, 6H); 4.21 (s, 3H); 5.80 (s, 1H); 6.2 (d, q, 1H); 6.57 (d, d, 1H); 7.43 (br s, 1H); 7.61 (s, 1H). The NMR was indicative of a cis:trans mixture of 1:7.
Applying the methods described in Equations 1-8 and Examples 1-5, one skilled in the art can prepare the compounds of Tables I-Va.
______________________________________TABLE OF STRUCTURES______________________________________General Structure I ##STR22##General Structure II ##STR23##General Structure III ##STR24##L-2 is ##STR25##L-3 is ##STR26##General Structure IIIa ##STR27##L-2 is ##STR28##General Structure IIIb ##STR29##L-2 is ##STR30##L-3 is ##STR31##General Structure IV ##STR32##General Structure V ##STR33##L-2 and L-3 are as in General Structure III.General Structure Va ##STR34##L-2 and L-3 are as in General Structure IIIa.______________________________________
TABLE I______________________________________General Structure IR R.sub.1 R.sub.3 E X Y Z m.p. (.degree.C.)______________________________________H H H S CH.sub.3 CH.sub.3 CH 142-145H H H S CH.sub.3 OCH.sub.3 CH 141-143H H H S OCH.sub.3 OCH.sub.3 CH 131-134H H H S CH.sub.3 CH.sub.3 N 165-169H H H S CH.sub.3 OCH.sub.3 N 152-156H H H S OCH.sub.3 OCH.sub.3 N 140-142H H H S Cl OCH.sub.3 CH 186-191H H H SO CH.sub.3 CH.sub.3 CHH H H SO CH.sub.3 OCH.sub.3 CHH H H SO OCH.sub.3 OCH.sub.3 CHH H H SO CH.sub.3 CH.sub.3 NH H H SO CH.sub.3 OCH.sub.3 NH H H SO OCH.sub.3 OCH.sub.3 NH H H SO Cl OCH.sub.3 CHH H H SO.sub.2 CH.sub.3 CH.sub.3 CH 210-212H H H SO.sub.2 CH.sub.3 OCH.sub.3 CHH H H SO.sub.2 OCH.sub.3 OCH.sub.3 CH 226-229H H H SO.sub.2 CH.sub.3 CH.sub.3 N 185-188H H H SO.sub.2 CH.sub.3 OCH.sub.3 NH H H SO.sub.2 OCH.sub.3 OCH.sub.3 N 165-179H H H SO.sub.2 Cl OCH.sub.3 CH 207-209H H H Se CH.sub.3 CH.sub.3 CH 187-190H H H Se CH.sub.3 OCH.sub.3 CH 165-167H H H Se OCH.sub.3 OCH.sub.3 CH 184-186H H H Se CH.sub.3 CH.sub.3 N 177-181H H H Se CH.sub.3 OCH.sub.3 N 163-166H H H Se OCH.sub.3 OCH.sub.3 N 147-151H H H Se Cl OCH.sub.3 CHCH.sub.3 H H Se OCH.sub.3 OCH.sub.3 CHCH.sub.3 H CH.sub.3 Se CH.sub.3 OCH.sub.3 CHH CH.sub.3 H Se OCH.sub.3 OCH.sub.3 CHH H CH.sub.3 S CH.sub.3 CH.sub.3 CH 143-147H H CH.sub.3 S CH.sub.3 OCH.sub.3 CH 136-139H H CH.sub.3 S OCH.sub.3 OCH.sub.3 CH 148-150H H CH.sub.3 S CH.sub.3 CH.sub.3 N 151-153H H CH.sub.3 S CH.sub.3 OCH.sub.3 N 164-169H H CH.sub.3 S OCH.sub.3 OCH.sub.3 N 154-160H H CH.sub.3 S Cl OCH.sub.3 CH 141-143H H CH.sub.3 Se CH.sub.3 CH.sub.3 CH 155-158H H CH.sub.3 Se OCH.sub.3 CH.sub.3 CH 159-161H H CH.sub.3 Se OCH.sub.3 OCH.sub.3 CH 145-148.5H H CH.sub.3 Se CH.sub.3 CH.sub.3 N 173-176H H CH.sub.3 Se OCH.sub.3 CH.sub.3 N 185-186.5H H CH.sub.3 Se OCH.sub.3 OCH.sub.3 N 182.5-184H H CH.sub.3 Se Cl OCH.sub.3 CHH H CH.sub.3 SO CH.sub.3 CH.sub.3 CHH H CH.sub.3 SO CH.sub.3 OCH.sub.3 CHH H CH.sub.3 SO OCH.sub.3 OCH.sub.3 CHH H CH.sub.3 SO CH.sub.3 CH.sub.3 NH H CH.sub.3 SO CH.sub.3 OCH.sub.3 NH H CH.sub.3 SO OCH.sub.3 OCH.sub.3 NH H CH.sub.3 SO Cl OCH.sub.3 CHH H CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 CHH H CH.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 CHH H CH.sub.3 SO.sub.2 OCH.sub.3 OCH.sub.3 CHH H CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 NH H CH.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 NH H CH.sub.3 SO.sub.2 OCH.sub.3 OCH.sub.3 NH H CH.sub.3 SO.sub.2 Cl OCH.sub.3 CH______________________________________
TABLE II______________________________________General Structure II m.p.W R R.sub.1 X Y Z (.degree.C.)______________________________________C.tbd.CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CHC.tbd.CHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CHC.tbd.CHCH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CHC.tbd.CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 NC.tbd.CHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 NC.tbd.CHCH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 NC.tbd.CHCH.sub.2 CH.sub.3 H H Cl OCH.sub.3 CHC.tbd.C--CH.sub.2 Ph H H CH.sub.3 CH.sub.3 CHC.tbd.C--CH.sub.2 Ph H H CH.sub.3 OCH.sub.3 CHC.tbd.C--CH.sub.2 Ph H H OCH.sub.3 OCH.sub.3 CHC.tbd.C--CH.sub.2 Ph H H CH.sub.3 CH.sub.3 NC.tbd.C--CH.sub.2 Ph H H CH.sub.3 OCH.sub.3 NC.tbd.C--CH.sub.2 Ph H H OCH.sub.3 OCH.sub.3 NC.tbd.C--CH.sub.2 Ph H H Cl CH.sub.3 CHC.tbd.C--CH.sub.2 Br H H CH.sub.3 CH.sub.3 CHC.tbd.C--CH.sub.2 Br H H CH.sub.3 OCH.sub.3 CHC.tbd.C--CH.sub.2 Br H H OCH.sub.3 OCH.sub.3 CHC.tbd.C--CH.sub.2 Br H H CH.sub.3 CH.sub.3 NC.tbd.C--CH.sub.2 Br H H CH.sub.3 OCH.sub.3 NC.tbd.C--CH.sub.2 Br H H OCH.sub.3 OCH.sub.3 NC.tbd.C--CH.sub.2 Br H H Cl OCH.sub.3 CHC.tbd.C--Ph H H CH.sub.3 CH.sub.3 CHC.tbd.C--Ph H H CH.sub.3 OCH.sub.3 CHC.tbd.C--Ph H H OCH.sub.3 OCH.sub.3 CHC.tbd.C--Ph H H CH.sub.3 CH.sub.3 NC.tbd.C--Ph H H CH.sub.3 OCH.sub.3 NC.tbd.C--Ph H H OCH.sub.3 OCH.sub.3 NC.tbd.C--Ph H H Cl OCH.sub.3 CHC.tbd.CCH.sub.2 OCH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CHC.tbd.CCH.sub.2 OCH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHC.tbd.CCH.sub.2 OCH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 NC.tbd.CCH.sub.2 OCH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 NC.tbd.CCH.sub.2 OCH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 NC.tbd.CCH.sub.2 OCH.sub.3 CH.sub.3 H Cl OCH.sub.3 CHC.tbd.CCH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CHC.tbd.CCH.sub.2 Cl H CH.sub.3 OCH.sub.3 OCH.sub.3 NC.tbd.CCH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH.sub.3 CHC.tbd.C--CH.sub.2 CH.sub.3 H SCH.sub.3 OCH.sub.3 CH.sub.3 CHC.tbd.C--CH.sub.2 CH.sub.3 H SCH.sub.3 OCH.sub.3 OCH.sub.3 NC.tbd.C--CH.sub.2 CH.sub.3 H Cl OCH.sub.3 OCH.sub.3 NC.tbd.C--CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH.sub.3 NC.tbd.C--CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 OCH.sub.3 NC.tbd.C--CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 OCH.sub.3 CHC.tbd.C--CH.sub.2 CH.sub.3 H OCH.sub.3 Cl OCH.sub.3 CH______________________________________
TABLE III__________________________________________________________________________General Structure III m.p.L n W R R.sub.1 R.sub.2 X Y Z (.degree.C.)__________________________________________________________________________L-2 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCH.sub.2 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCN H H -- Cl OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHPh H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- Cl OCH.sub.3 CHL-2 0 ##STR35## H H -- CH.sub.3 CH.sub.3 CH 186-190L-2 0 ##STR36## H H -- CH.sub.3 OCH.sub.3 CH 182-185L-2 0 ##STR37## H H -- OCH.sub.3 OCH.sub.3 CH 178-180L-2 0 ##STR38## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR39## H H -- CH.sub.3 OCH.sub.3 N 152-156L-2 0 ##STR40## H H -- OCH.sub.3 OCH.sub.3 N 145-148L-2 0 ##STR41## H H -- Cl OCH.sub.3 CH 192-195L-2 0 ##STR42## H H -- CH.sub.3 CH.sub.3 CH 208-211L-2 0 ##STR43## H H -- CH.sub.3 OCH.sub.3 CH 190-192L-2 0 ##STR44## H H -- OCH.sub.3 OCH.sub.3 CH 161-164L-2 0 ##STR45## H H -- NHCH.sub.3 OCH.sub.2 CH.sub.3 N 180-185L-2 0 ##STR46## H H -- CH.sub.3 OCH.sub.3 N 169-171L-2 0 ##STR47## H H -- OCH.sub.3 OCH.sub.3 N 154-161L-2 0 ##STR48## H H -- Cl OCH.sub.3 CH 167-169L-2 0 ##STR49## H H -- CH.sub.3 CH.sub.3 CHL-2 0 ##STR50## H H -- CH.sub.3 OCH.sub.3 CHL-2 0 ##STR51## H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR52## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR53## H H -- CH.sub.3 OCH.sub.3 NL-2 0 ##STR54## H H -- OCH.sub.3 OCH.sub.3 NL-2 0 ##STR55## H H -- Cl OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CN)CHCN H H -- Cl OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CH CHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 ##STR56## CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR57## H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 OSO.sub.2 Ph H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHSCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CH 185-192L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CH 189-194L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 CH 142-149L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 N 145-150L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 N 138-144L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- Cl OCH.sub.3 CH 123-130L-2 0 CHCHNO.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHNO.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHNO.sub.2 H H -- OCH.sub.3 OCH.sub.3 CH 86-91L-2 0 CHCHNO.sub.2 H H -- CH.sub.3 OCH.sub.3 N 182-188L-2 0 CHCHNO.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHNO.sub.2 H H -- Cl OCH.sub.3 CH 88-93L-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CH 214-215L-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CH C(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub. 3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(NO.sub.2)CO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(NO.sub.2)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(NO.sub.2)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(NO.sub.2)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(NO.sub.2)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(NO.sub.2)CO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C CH H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CH H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CH H H -- CH.sub.3 CH.sub.3 NL-2 0 C CH H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CH H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CH H H -- Cl OCH.sub.3 CHL-2 0 C CPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CPh H H -- CH.sub.3 CH.sub.3 NL-2 0 C CPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CPh H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OH H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 Cl H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 CN H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub. 3 CH.sub.3 NL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 SCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCH.sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub. 3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCHPh H H -- Cl OCH.sub.3 CHL-2 1 C CH H H -- CH.sub.3 CH.sub.3 CHL-2 1 C CH H H -- CH.sub.3 OCH.sub.3 CHL-2 1 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 C CH H H -- CH.sub.3 CH.sub.3 NL-2 1 C CH H H -- CH.sub.3 OCH.sub.3 NL-2 1 C CH H H -- OCH.sub.3 OCH.sub.3 NL-2 1 C CH H H -- Cl OCH.sub.3 CHL-2 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-2 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-2 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-2 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-2 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-2 1 C CCH.sub.2 Br H H -- Cl OCH.sub. 3 CHL-2 1 C CPh H H -- CH.sub.3 CH.sub.3 CHL-2 1 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-2 1 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 C CPh H H -- CH.sub.3 CH.sub.3 NL-2 1 C CPh H H -- CH.sub.3 OCH.sub.3 NL-2 1 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-2 1 C CPh H H -- Cl OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- Cl OCH.sub.3 CHL-2 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-2 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-2 1 C CH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-2 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-2 1 C CH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-2 1 C CH CH.sub.3 H -- Cl OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- Cl OCH.sub.3 CHL-2 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-2 1 C CH H CH.sub.3 -- OCH.sub.3 CH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCH.sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHCN H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHCN H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHOCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub. 3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR58## H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 ##STR59## H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 ##STR60## H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR61## H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 ##STR62## H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 ##STR63## H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 ##STR64## H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR65## H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 ##STR66## H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 ##STR67## H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR68## H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 ##STR69## H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 ##STR70## H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 ##STR71## H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR72## H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 ##STR73## H H CH.sub.3 CH.sub.3 OCH.sub.3L-3 CH 0 ##STR74## H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR75## H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 ##STR76## H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 ##STR77## H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 ##STR78## H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CN)CHCN H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CN)CHCN H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHSO.sub.2 N(CH.sub.3 ).sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR79## CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR80## H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 OSO.sub.2 Ph H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHSCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CH H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CH H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CH H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CH H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CH H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CH H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 OH H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 OH H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OH H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OH H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 OH H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OH H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OH H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 Cl H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 Cl H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 Cl H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 Cl H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 Cl H H CH.sub.3 CH.sub. 3 OCH.sub.3 NL-3 0 C CCH.sub.2 Cl H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 Cl H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 Br H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 CN H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 CN H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 CN H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 CN H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 CN H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 CN H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 CN H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C CCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 SCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C CCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 SCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 SCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCCH.sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub. 3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCCHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCCHPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCCHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCCHCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 C CH H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 C CH H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 C CH H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 C CH H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 C CH H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 C CH H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 C CH H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 C CCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 C CCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 C CCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 C CCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 C CCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 C CCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 C CCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 C CCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 C CCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 C CCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 C CCH.sub.2 Br H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 C CPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 C CPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 C CPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 C CPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 C CPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 C CPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 C CPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub. 2 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 Cl OCH.sub.3 CHL-3 1 C CH CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 C CH CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 C CH CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 C CH CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 C CH CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 C CH CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 C CH CH.sub.3 H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 Cl OCH.sub.3 CHL-3 1 C CH H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 C CH H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 C CH H CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CHL-3 0 CHCHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 N 159-162L-3 0 CHCHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CH 155-158L-3 0 CHCHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CH 154-156L-4 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-4 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-4 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-4 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 CHCH.sub.2 H H -- Cl OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 CHCHCN H H -- CH.sub.3 CH.sub.3 CHL-4 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHCN H H -- CH.sub.3 CH.sub.3 NL-4 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 NL-4 0 CHCHCN H H -- OCH.sub.3 OCH.sub. NL-4 0 CHCHCN H H -- Cl OCH.sub.3 CHL-4 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 CHCHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 CHCHPh H H -- CH.sub.3 CH.sub.3 CHL-4 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHPh H H -- CH.sub.3 CH.sub.3 NL-4 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 NL-4 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 NL-4 0 CHCHPh H H -- Cl OCH.sub.3 CHL-4 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 CHL-4 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 NL-4 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHPh H H -- Cl OCH.sub.3 CHL-4 0 ##STR81## H H -- CH.sub.3 CH.sub.3 CHL-4 0 ##STR82## H H -- CH.sub.3 OCH.sub.3 CHL-4 0 ##STR83## H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 ##STR84## H H -- CH.sub.3 CH.sub.3 NL-4 0 ##STR85## H H -- CH.sub.3 OCH.sub.3 NL-4 0 ##STR86## H H -- OCH.sub.3 OCH.sub.3 NL-4 0 ##STR87## H H -- Cl OCH.sub.3 CHL-4 0 ##STR88## H H -- CH.sub.3 CH.sub.3 CHL-4 0 ##STR89## H H -- CH.sub.3 OCH.sub.3 CHL-4 0 ##STR90## H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 ##STR91## H H -- CH.sub.3 CH.sub.3 NL-4 0 ##STR92## H H -- CH.sub.3 OCH.sub.3 NL-4 0 ##STR93## H H -- OCH.sub.3 OCH.sub.3 NL-4 0 ##STR94## H H -- Cl OCH.sub.3 CHL-4 0 ##STR95## H H -- CH.sub.3 CH.sub.3L-4 CH 0 ##STR96## H H -- CH.sub.3 OCH.sub.3 CHL-4 0 ##STR97## H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 ##STR98## H H -- CH.sub.3 CH.sub.3 NL-4 0 ##STR99## H H -- CH.sub.3 OCH.sub.3 NL-4 0 ##STR100## H H -- OCH.sub. 3 OCH.sub.3 NL-4 0 ##STR101## H H -- Cl OCH.sub.3 CHL-4 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 CHL-4 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 NL-4 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 NL-4 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C(CN)CHCN H H -- Cl OCH.sub.3 CHL-4 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-4 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-4 0 CHCHSO.sub.2 N(CH.sub.3 ).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-4 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3L-4 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 ##STR102## CH.sub.3 H -- OCH.sub. 3 OCH.sub.3 CHL-4 0 ##STR103## H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-4 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 OSO.sub.2 Ph H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHSCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CH H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CH H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CH H H -- CH.sub.3 CH.sub.3 NL-4 0 C CH H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CH H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CH H H -- Cl OCH.sub.3 CHL-4 0 C CPh H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CPh H H -- CH.sub.3 CH.sub.3 NL-4 0 C CPh H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CPh H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 OC(O)CH.sub. 3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OH H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 Cl H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 CN H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-4 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 0 C CCH.sub.2 SCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-4 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-4 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-4 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-4 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-4 1 HCCH.sub.2 H H -- Cl OCH.sub.3 CHL-4 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-4 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-4 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-4 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-4 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-4 1 HCC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-4 1 HCC(CH.sub.3)CH.sub.2 CH.sub. 2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-4 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-4 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-4 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-4 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-4 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-4 1 HCCHPh H H -- CH.sub.3 CH.sub.3 CHL-4 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 CHL-4 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 HCCHPh H H -- CH.sub.3 CH.sub.3 NL-4 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 NL-4 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 NL-4 1 HCCHPh H H -- Cl OCH.sub.3 CHL-4 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 1 HCCHCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 1 C CH H H -- CH.sub.3 CH.sub.3 CHL-4 1 C CH H H -- CH.sub.3 OCH.sub.3 CHL-4 1 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 C CH H H -- CH.sub.3 CH.sub.3 NL-4 1 C CH H H -- CH.sub.3 OCH.sub.3 NL-4 1 C CH H H -- OCH.sub.3 OCH.sub.3 NL-4 1 C CH H H -- Cl OCH.sub.3 CHL-4 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-4 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-4 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-4 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-4 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-4 1 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-4 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-4 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-4 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-4 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-4 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-4 1 C CCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-4 1 C CPh H H -- CH.sub.3 CH.sub.3 CHL-4 1 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-4 1 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-4 1 C CPh H H -- CH.sub.3 CH.sub.3 NL-4 1 C CPh H H -- CH.sub.3 OCH.sub.3 NL-4 1 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-4 1 C CPh H H -- Cl OCH.sub.3 CHL-4 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-4 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-4 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-4 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-4 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-4 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-4 1 CHCH.sub.2 CH.sub.3 H -- Cl OCH.sub.3 CHL-4 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-4 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-4 1 C CH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-4 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-4 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-4 1 C CH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-4 1 C CH CH.sub.3 H -- Cl OCH.sub.3 CHL-4 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 CHL-4 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 CHL-4 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-4 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 NL-4 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 NL-4 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-4 1 CHCH.sub.2 H CH.sub.3 -- Cl OCH.sub.3 CHL-4 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-4 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-4 1 C CH H CH.sub.3 -- OCH.sub.3 CH.sub.3 CHL-5 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-5 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-5 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-5 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 CHCH.sub.2 H H -- Cl OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 CHCHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub. 3 CHL-5 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 CHCHCN H H -- CH.sub.3 CH.sub.3 CHL-5 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 CHL-5 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHCN H H -- CH.sub.3 CH.sub.3 NL-5 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 NL-5 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 NL-5 0 CHCHCN H H -- Cl OCH.sub.3 CHL-5 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 CHCHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 CHCHPh H H -- CH.sub.3 CH.sub.3 CHL-5 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 CHL-5 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHPh H H -- CH.sub.3 CH.sub.3 NL-5 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 NL-5 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 NL-5 0 CHCHPh H H -- Cl OCH.sub.3 CHL-5 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 CHL-5 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 NL-5 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHPh H H -- Cl OCH.sub.3 CHL-5 0 ##STR104## H H -- CH.sub.3 CH.sub.3 CHL-5 0 ##STR105## H H -- CH.sub.3 OCH.sub.3 CHL-5 0 ##STR106## H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 ##STR107## H H -- CH.sub.3 CH.sub.3 NL-5 0 ##STR108## H H -- CH.sub.3 OCH.sub.3 NL-5 0 ##STR109## H H -- OCH.sub.3 OCH.sub.3 NL-5 0 ##STR110## H H -- Cl OCH.sub.3 CHL-5 0 ##STR111## H H -- CH.sub.3 CH.sub.3 CHL-5 0 ##STR112## H H -- CH.sub.3 OCH.sub.3 CHL-5 0 ##STR113## H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 ##STR114## H H -- CH.sub.3 CH.sub.3 NL-5 0 ##STR115## H H -- CH.sub. 3 OCH.sub.3 NL-5 0 ##STR116## H H -- OCH.sub.3 OCH.sub.3 NL-5 0 ##STR117## H H -- Cl OCH.sub.3 CHL-5 0 ##STR118## H H -- CH.sub.3 CH.sub.3 CHL-5 0 ##STR119## H H -- CH.sub.3 OCH.sub.3 CHL-5 0 ##STR120## H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 ##STR121## H H -- CH.sub.3 CH.sub.3 NL-5 0 ##STR122## H H -- CH.sub.3 OCH.sub.3 NL-5 0 ##STR123## H H -- OCH.sub.3 OCH.sub.3 NL-5 0 ##STR124## H H -- Cl OCH.sub.3 CHL-5 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 CHL-5 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 NL-5 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 NL-5 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C(CN)CHCN H H -- Cl OCH.sub.3 CHL-5 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-5 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-5 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-5 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 ##STR125## CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-5 0 ##STR126## H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-5 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHCH.sub.2 OSO.sub.2 Ph H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 CHCHSCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CH H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CH H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CH H H -- CH.sub.3 CH.sub.3 NL-5 0 C CH H H -- CH.sub. 3 OCH.sub.3 NL-5 0 C CH H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CH H H -- Cl OCH.sub.3 CHL-5 0 C CPh H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CPh H H -- CH.sub.3 CH.sub.3 NL-5 0 C CPh H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CPh H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OH H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 Cl H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 CN H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-5 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 0 C CCH.sub.2 SCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-5 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-5 1 HCCH.sub.2 H H -- OCH.sub. 3 OCH.sub.3 CHL-5 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-5 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-5 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-5 1 HCCH.sub.2 H H -- Cl OCH.sub.3 CHL-5 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-5 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-5 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-5 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-5 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-5 1 HCC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-5 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-5 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-5 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-5 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-5 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-5 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-5 1 HCCHPh H H -- CH.sub.3 CH.sub.3 CHL-5 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 CHL-5 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 HCCHPh H H -- CH.sub.3 CH.sub.3 NL-5 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 NL-5 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 NL-5 1 HCCHPh H H -- Cl OCH.sub.3 CHL-5 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 1 HCCHCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 1 C CH H H -- CH.sub.3 CH.sub.3 CHL-5 1 C CH H H -- CH.sub.3 OCH.sub.3 CHL-5 1 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 C CH H H -- CH.sub.3 CH.sub.3 NL-5 1 C CH H H -- CH.sub.3 OCH.sub.3 NL-5 1 C CH H H -- OCH.sub.3 OCH.sub.3 NL-5 1 C CH H H -- Cl OCH.sub.3 CHL-5 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-5 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-5 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-5 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-5 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-5 1 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-5 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-5 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-5 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-5 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-5 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-5 1 C C CH.sub.2 Br H H -- Cl OCH.sub.3 CHL-5 1 C CPh H H -- CH.sub.3 CH.sub.3 CHL-5 1 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-5 1 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-5 1 C CPh H H -- CH.sub.3 CH.sub.3 NL-5 1 C CPh H H -- CH.sub.3 OCH.sub.3 NL-5 1 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-5 1 C CPh H H -- Cl OCH.sub.3 CHL-5 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-5 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-5 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-5 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-5 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-5 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-5 1 CHCH.sub.2 CH.sub.3 H -- Cl OCH.sub.3 CHL-5 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-5 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-5 1 C CH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-5 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-5 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-5 1 C CH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-5 1 C CH CH.sub.3 H -- Cl OCH.sub.3 CHL-5 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 CHL-5 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 CHL-5 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-5 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 NL-5 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 NL-5 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-5 1 CHCH.sub.2 H CH.sub.3 -- Cl OCH.sub.3 CHL-5 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-5 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-5 1 C CH H CH.sub.3 -- OCH.sub.3 CH.sub.3 CHL-6 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCH.sub.2 H H -- Cl OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 CHCHCN H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHCN H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHCN H H -- Cl OCH.sub.3 CHL-6 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 CHCHBr H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHBr H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHBr H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHBr H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHBr H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHBr H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHBr H H -- Cl OCH.sub.3 CHL-6 0 CHCHCF.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHCF.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHCF.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHCF.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHCF.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHCF.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHCF.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C(CH.sub. 3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 CHCHPh H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHPh H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHPh H H -- Cl OCH.sub.3 CHL-6 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 CHL-6 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 NL-6 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHPh H H -- Cl OCH.sub.3 CHL-6 0 ##STR127## H H -- CH.sub.3 CH.sub.3 CHL-6 0 ##STR128## H H -- CH.sub.3 OCH.sub.3 CHL-6 0 ##STR129## H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 ##STR130## H H -- CH.sub.3 CH.sub.3 NL-6 0 ##STR131## H H -- CH.sub.3 OCH.sub.3 NL-6 0 ##STR132## H H -- OCH.sub.3 OCH.sub.3 NL-6 0 ##STR133## H H -- Cl OCH.sub.3 CHL-6 0 ##STR134## H H -- CH.sub.3 CH.sub.3 CHL-6 0 ##STR135## H H -- CH.sub.3 OCH.sub.3 CHL-6 0 ##STR136## H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 ##STR137## H H -- CH.sub.3 CH.sub.3 NL-6 0 ##STR138## H H -- CH.sub.3 OCH.sub.3 NL-6 0 ##STR139## H H -- OCH.sub.3 OCH.sub.3 NL-6 0 ##STR140## H H -- Cl OCH.sub.3 CHL-6 0 ##STR141## H H -- CH.sub.3 CH.sub.3 CHL-6 0 ##STR142## H H -- CH.sub.3 OCH.sub.3 CHL-6 0 ##STR143## H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 ##STR144## H H -- CH.sub.3 CH.sub.3 NL-6 0 ##STR145## H H -- CH.sub.3 OCH.sub.3 NL-6 0 ##STR146## H H -- OCH.sub.3 OCH.sub.3 NL-6 0 ##STR147## H H -- Cl OCH.sub.3 CHL-6 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 CHL-6 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 NL-6 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 NL-6 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C(CN)CHCN H H -- Cl OCH.sub.3 CHL-6 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-6 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-6 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-6 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 ##STR148## CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-6 0 ##STR149## H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-6 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHCH.sub.2 OSO.sub.2 Ph H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 CHCHSCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CH H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CH H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CH H H -- CH.sub.3 CH.sub.3 NL-6 0 C CH H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CH H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CH H H -- Cl OCH.sub.3 CHL-6 0 C CPh H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CPh H H -- CH.sub.3 CH.sub.3 NL-6 0 C CPh H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CPh H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OH H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 Cl H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-6 0 C C CH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub. 2 CN H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-6 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub. 3 CH.sub.3 CHL-6 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 0 C CCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 0 C CCH.sub.2 SCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-6 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-6 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-6 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-6 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-6 1 HCCH.sub.2 H H -- Cl OCH.sub.3 CHL-6 1 BrCCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-6 1 BrCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-6 1 BrCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 BrCCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-6 1 BrCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-6 1 BrCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-6 1 BrCCH.sub.2 H H -- Cl OCH.sub.3 CHL-6 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-6 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-6 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 HCC(CH.sub.3).sub. 2 H H -- CH.sub.3 CH.sub.3 NL-6 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-6 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-6 1 HCC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-6 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-6 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-6 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-6 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-6 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-6 1 HCC(CH.sub.3 )CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-6 1 HCCHPh H H -- CH.sub.3 CH.sub.3 CHL-6 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 CHL-6 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 HCCHPh H H -- CH.sub.3 CH.sub.3 NL-6 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 NL-6 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 NL-6 1 HCCHPh H H -- Cl OCH.sub.3 CHL-6 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 1 HCCHCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 1 HCCHCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-6 1 HCCHCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-6 1 HCCHCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 HCCHCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-6 1 HCCHCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-6 1 HCCHCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-6 1 HCCHCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-6 1 C CH H H -- CH.sub.3 CH.sub.3 CHL-6 1 C CH H H -- CH.sub.3 OCH.sub.3 CHL-6 1 C CH H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 C CH H H -- CH.sub.3 CH.sub.3 NL-6 1 C CH H H -- CH.sub.3 OCH.sub.3 NL-6 1 C CH H H -- OCH.sub.3 OCH.sub.3 NL-6 1 C CH H H -- Cl OCH.sub.3 CHL-6 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-6 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-6 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 C CCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-6 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-6 1 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-6 1 C CCH.sub.3 H H -- Cl OCH.sub.3 CHL-6 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-6 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-6 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-6 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-6 1 C CCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-6 1 C CCH.sub.2 Br H H -- Cl OCH.sub. 3 CHL-6 1 C CPh H H -- CH.sub.3 CH.sub.3 CHL-6 1 C CPh H H -- CH.sub.3 OCH.sub.3 CHL-6 1 C CPh H H -- OCH.sub.3 OCH.sub.3 CHL-6 1 C CPh H H -- CH.sub.3 CH.sub.3 NL-6 1 C CPh H H -- CH.sub.3 OCH.sub.3 NL-6 1 C CPh H H -- OCH.sub.3 OCH.sub.3 NL-6 1 C CPh H H -- Cl OCH.sub.3 CHL-6 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-6 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-6 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-6 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-6 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-6 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-6 1 CHCH.sub.2 CH.sub.3 H -- Cl OCH.sub.3 CHL-6 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-6 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-6 1 C CH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-6 1 C CH CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-6 1 C CH CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-6 1 C CH CH.sub.3 H -- OCH.sub. 3 OCH.sub.3 NL-6 1 C CH CH.sub.3 H -- Cl OCH.sub.3 CHL-6 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 CHL-6 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 CHL-6 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-6 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 NL-6 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 NL-6 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-6 1 CHCH.sub.2 H CH.sub.3 -- Cl OCH.sub.3 CHL-6 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-6 1 C CH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-6 1 C CH H CH.sub.3 -- OCH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CH 185-192L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CH 189-194L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- OCH.sub.3 OH.sub.3 CH 142-149L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 N 145-150L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 N 138-144L-2 0 C(CH.sub.3)CHCH.sub.2 OH H H -- Cl OCH.sub.3 CH 123-130L-2 0 CHC(CN).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CH 214-215L-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub. 2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub. 2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CH__________________________________________________________________________
TABLE IIIa__________________________________________________________________________General Structure IIIa m.p.L n W R R.sub.1 R.sub.2 X Y Z (.degree.C.)__________________________________________________________________________L-2 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCH.sub.2 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCN H H -- Cl OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHPh H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- Cl OCH.sub.3 CHL-2 0 ##STR150## H H -- CH.sub.3 CH.sub.3 CHL-2 0 ##STR151## H H -- CH.sub.3 OCH.sub.3 CHL-2 0 ##STR152## H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR153## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR154## H H -- CH.sub.3 OCH.sub.3 NL-2 0 ##STR155## H H -- OCH.sub.3 OCH.sub.3 NL-2 0 ##STR156## H H -- Cl OCH.sub.3 CHL-2 0 ##STR157## H H -- CH.sub.3 CH.sub.3 CHL-2 0 ##STR158## H H -- CH.sub.3 OCH.sub.3 CHL-2 0 ##STR159## H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR160## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR161## H H -- CH.sub.3 OCH.sub.3 NL-2 0 ##STR162## H H -- OCH.sub.3 OCH.sub.3 NL-2 0 ##STR163## H H -- Cl OCH.sub.3 CHL-2 0 ##STR164## H H -- CH.sub.3 CH.sub.3 CHL-2 0 ##STR165## H H -- CH.sub.3 OCH.sub. 3 CHL-2 0 ##STR166## H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR167## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR168## H H -- CH.sub.3 OCH.sub.3 NL-2 0 ##STR169## H H -- OCH.sub.3 OCH.sub.3 NL-2 0 ##STR170## H H -- Cl OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CN)CHCN H H -- Cl OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub. 3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 ##STR171## CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR172## H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 OSO.sub.2 Ph H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub. 2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHSCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCH H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCH H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCH H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCH H H -- CH.sub.3 CH.sub.3 NL-2 0 CCH H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCH H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCH H H -- Cl OCH.sub.3 CHL-2 0 CCPh H H -- CH.sub.3 CH.sub. 3 CHL-2 0 CCPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCPh H H -- CH.sub.3 CH.sub.3 NL-2 0 CCPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCPh H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CC CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OH H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C CCH.sub.2 Cl H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 CN H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 SCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCH.sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCC(CH.sub. 3)CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCHPh H H -- Cl OCH.sub.3 CHL-2 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HC CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCHCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 CH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCH H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 CH.sub.3 NL-2 1 CCH H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCH H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCH H H -- Cl OCH.sub.3 CHL-2 1 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 1 C CCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 1 CCCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 CCCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-2 1 C CCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-2 1 CCCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-2 1 CCPh H H -- CH.sub.3 CH.sub.3 CHL-2 1 CCPh H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCPh H H -- CH.sub.3 CH.sub.3 NL-2 1 CCPh H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCPh H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCPh H H -- Cl OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- Cl OCH.sub.3 CHL-2 1 CCH CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-2 1 CCH CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCH CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-2 1 CCH CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-2 1 CCH CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCH CH.sub.3 H -- Cl OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub. 3 -- OCH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- Cl OCH.sub.3 CHL-2 1 CCH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-2 1 CCH H CH.sub.3 -- OCH.sub.3 CH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub. 3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.3 ##STR173## NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 NHCH.sub.3 NL-2 0 CHCH.sub.2 H H -- OCH.sub.2 CH.sub.3 NHCH.sub.3 NL-2 0 CHCH.sub.2 H H -- OCF.sub.2 H OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.2 CH.sub.3 CH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.2 CF.sub.3 N__________________________________________________________________________
TABLE IIIb__________________________________________________________________________General Structure IIIb m.p.L n W R R.sub.1 R.sub.2 X Y Z (.degree.C.)__________________________________________________________________________L-2 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCH.sub.2 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3 )CHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCN H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHCN H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHCN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHCN H H -- Cl OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHOCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHPh H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHPh H H -- CH.sub. 3 OCH.sub.3 NL-2 0 CHCHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHPh H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHPh H H -- Cl OCH.sub.3 CHL-2 0 ##STR174## H H -- CH.sub.3 CH.sub.3 CHL-2 0 ##STR175## H H -- CH.sub.3 OCH.sub.3 CHL-2 0 ##STR176## H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR177## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR178## H H -- CH.sub.3 OCH.sub.3 NL-2 0 ##STR179## H H -- OCH.sub.3 OCH.sub.3 NL-2 0 ##STR180## H H -- Cl OCH.sub.3 CHL-2 0 ##STR181## H H -- CH.sub.3 CH.sub.3 CHL-2 0 ##STR182## H H -- CH.sub.3 OCH.sub.3 CHL-2 0 ##STR183## H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR184## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR185## H H -- CH.sub.3 OCH.sub.3 NL-2 0 ##STR186## H H -- OCH.sub.3 OCH.sub.3 NL-2 0 ##STR187## H H -- Cl OCH.sub.3 CHL-2 0 ##STR188## H H -- CH.sub.3 CH.sub.3 CHL-2 0 ##STR189## H H -- CH.sub.3 OCH.sub. 3 CHL-2 0 ##STR190## H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR191## H H -- CH.sub.3 CH.sub.3 NL-2 0 ##STR192## H H -- CH.sub.3 OCH.sub.3 NL-2 0 ##STR193## H H -- OCH.sub.3 OCH.sub.3 NL-2 0 ##STR194## H H -- Cl OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CN)CHCN H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CN)CHCN H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CN)CHCN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CN)CHCN H H -- Cl OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 ##STR195## CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 0 ##STR196## H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 OSO.sub.2 Ph H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHCHSCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCH H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCH H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCH H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCH H H -- CH.sub.3 CH.sub.3 NL-2 0 CCH H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCH H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCH H H -- Cl OCH.sub.3 CHL-2 0 C CPh H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCPh H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCPh H H -- CH.sub.3 CH.sub.3 NL-2 0 CCPh H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCPh H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCPh H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OC(O)CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OH H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OH H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OH H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 Cl H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 Cl H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 Cl H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-2 0 C CCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 CN H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 CN H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 CN H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 CN H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 C CCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 C CCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 0 CCCH.sub.2 SCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 SCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CCCH.sub.2 SCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCCH.sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCH.sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCH.sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCH.sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCC(CH.sub.3)CH.sub.2 CH.sub.2 CHC(CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCCHPh H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCHPh H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCHPh H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCHPh H H -- Cl OCH.sub.3 CHL-2 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 HCCHCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 1 HCCHCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 1 HCCHCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 HCCHCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 CH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCH H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 CH.sub.3 NL-2 1 CCH H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCH H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCH H H -- Cl OCH.sub.3 CHL-2 1 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 1 CCCH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.3 H H -- CH.sub.3 CH.sub.3 NL-2 1 CCCH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.3 H H -- Cl OCH.sub.3 CHL-2 1 C CCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 CHL-2 1 CCCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCCH.sub.2 Br H H -- CH.sub.3 CH.sub.3 NL-2 1 CCCH.sub.2 Br H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.2 Br H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCCH.sub.2 Br H H -- Cl OCH.sub.3 CHL-2 1 CCPh H H -- CH.sub.3 CH.sub.3 CHL-2 1 CCPh H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCPh H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCPh H H -- CH.sub.3 CH.sub.3 NL-2 1 CCPh H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCPh H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCPh H H -- Cl OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 CH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- OCH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 CH.sub.3 H -- Cl OCH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 CH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 OCH.sub.3 CHL-2 1 CCH H H -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCH H H -- CH.sub.3 CH.sub.3 NL-2 1 CCH H H -- CH.sub.3 OCH.sub.3 NL-2 1 CCH H H -- OCH.sub.3 OCH.sub.3 NL-2 1 CCH H H -- Cl OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 CH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- CH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-2 1 CHCH.sub.2 H CH.sub.3 -- Cl OCH.sub.3 CHL-2 1 CCH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 CHL-2 1 CCH H CH.sub.3 -- OCH.sub.3 OCH.sub.3 NL-2 1 CCH H CH.sub.3 -- OCH.sub.3 CH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCH.sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCH.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CH CHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-4 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHCN H H CH.sub. 3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHCN H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHOCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHOCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3) CHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR197## H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 ##STR198## H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 ##STR199## H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR200## H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 ##STR201## H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 ##STR202## H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 ##STR203## H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR204## H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 ##STR205## H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 ##STR206## H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR207## H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 ##STR208## H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 ##STR209## H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 ##STR210## H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR211## H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 ##STR212## H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 ##STR213## H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR214## H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 ##STR215## H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 ##STR216## H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 ##STR217## H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CN)CHCN H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CN)CHCN H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CN)CHCN H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CHCHSO.sub.2 N(CH.sub.3).sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 C(CH.sub.3)CHCO.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 ##STR218## CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR219## H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 ##STR220## H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 C(CH.sub.2)CH.sub.2 CH.sub.2 CH(NO.sub.2)CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 OSO.sub.2 Ph H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CHCHSCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCH H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCH H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 C CH H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCH H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCH H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCH H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCH H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 C CPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub. 3 NL-3 0 CCCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 OC(O)CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 OH H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.2 OH H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OH H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OH H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 OH H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 OH H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 OH H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 Cl H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 C CCH.sub.2 Cl H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 Cl H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 Cl H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 Cl H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 Cl H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 Cl H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 Br H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 CN H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.2 CN H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 CN H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 CN H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 CN H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 CN H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 CN H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 OCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 OCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 OCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 C CCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 OSO.sub.2 CH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 0 CCCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 0 CCCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 SCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 0 CCCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 0 CCCH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 SCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 0 CCCH.sub.2 SCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCCH.sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCCH.sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCCH.sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3).sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCC(CH.sub.3)CH.sub.2 CHC(CH.sub.3).sub.2 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 CH.sub. 3 OCH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCCHPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCCHPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCCHPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCCHPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 HCCHCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 HCCHCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 HCCHCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CCH H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 C CH H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CCH H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CCH H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CCH H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CCH H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CCH H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CCCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CCCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CCCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 C CCH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CCCH.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CCCH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CCCH.sub.3 H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CCCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CCCH.sub.2 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CCCH.sub.2 Br H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CCCH.sub.2 Br H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CCPh H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CCPh H H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CCPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CCPh H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CCPh H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CCPh H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 C CPh H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 CH.sub.3 H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CCH H H CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CCH H H CH.sub.3 CH.sub.3 OCH.sub.3 OHL-3 1 CCH H H CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CCH H H CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CCH H H CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CCH H H CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CCH H H CH.sub.3 Cl OCH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 NL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CHCH.sub.2 H CH.sub.3 CH.sub.3 Cl OCH.sub.3 CHL-3 1 CCH H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHL-3 1 CCH H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NL-3 1 CCH H CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub. 3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub. 3 OCH.sub.3 CHL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CN)CO.sub.2 CH.sub.3 H H -- Cl OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 CH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 CHL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- CH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- OCH.sub.3 OCH.sub.3 NL-2 0 CHC(CO.sub.2 CH.sub.3).sub.2 H H -- Cl OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.2 CH.sub.3 CH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.2 CH.sub.3 NHCH.sub.3 NL-2 0 CHCH.sub.2 H H -- OCH.sub. 3 N(CH.sub.3).sub.2 NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 CH(CH.sub.3).sub.2 NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 CH.sub.2 OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- CH.sub.3 OCH.sub.2 CH.sub.2 F NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 CH(OCH.sub.3).sub.2 CHL-2 0 CHCH.sub.2 H H -- Br OCH.sub.3 CHL-2 0 CHCH.sub.2 H H -- OCH.sub.3 OCH.sub.2 CF.sub.3 NL-2 0 CHCH.sub.2 H H -- OCH.sub.3 H CH__________________________________________________________________________
TABLE IV__________________________________________________________________________General Structure IVA W R R.sub.1 X.sub.1 Y.sub.1 Y.sub.2 X.sub.2 Y.sub.3 X.sub.3 m.p. (.degree.C.)__________________________________________________________________________A-2 C.tbd.C--CH.sub.2 F H H CH.sub.3 O -- -- -- --A-2 C.tbd.C--CH.sub.2 F H H CH.sub.3 CH.sub.2 -- -- -- --A-2 C.tbd.C--CH.sub.2 F H H OCH.sub.3 O -- -- -- --A-2 C.tbd.C--CH.sub.2 F H H OCF.sub.2 H O -- -- -- --A-3 C.tbd.C--CH.sub.2 F H H CH.sub.3 -- -- -- -- --A-3 C.tbd.C--CH.sub.2 F H H OCH.sub.3 -- -- -- -- --A-3 C.tbd.C--CH.sub.2 F H H OCF.sub.2 H -- -- -- -- --A-4 C.tbd.C--CH.sub.2 F H H CH.sub.3 -- H -- -- --A-4 C.tbd.C--CH.sub.2 F H H OCH.sub.3 -- H -- -- --A-4 C.tbd.C--CH.sub.2 F H H CH.sub.3 -- CH.sub.3 -- -- --A-4 C.tbd.C--CH.sub.2 F H H OCH.sub.3 -- CH.sub.3 -- -- --A-5 C.tbd.C--CH.sub.2 F H H -- -- -- CH.sub.3 CH.sub.3 --A-5 C.tbd.C--CH.sub.2 F H H -- -- -- OCH.sub.3 CH.sub.3 --A-5 C.tbd.C--CH.sub.2 F H H -- -- -- CH.sub.3 CH.sub.2 CF.sub.3 --A-6 C.tbd.C--CH.sub.2 F H H -- -- -- -- -- CH.sub.3__________________________________________________________________________
TABLE V__________________________________________________________________________General Structure VL W A n X.sub.1 Y.sub.1 Y.sub.2 X.sub.2 Y.sub.3 X.sub.3 X.sub.4 Y.sub.4 m.p. (.degree.C.)__________________________________________________________________________L-2 ##STR221## A-2 O CH.sub.3 O -- -- -- -- -- --L-2 ##STR222## A-2 O OCH.sub.3 O -- -- -- -- -- --L-2 ##STR223## A-2 O CH.sub.3 CH -- -- -- -- -- --L-2 ##STR224## A-3 O OCH.sub.3 -- -- -- -- -- -- --L-2 ##STR225## A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-2 ##STR226## A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-2 ##STR227## A-6 O -- -- -- -- -- CH.sub.3 -- --L-3 ##STR228## A-2 O CH.sub.3 O -- -- -- -- -- --L-3 ##STR229## A-3 O OCH.sub.3 -- -- -- -- -- -- --L-3 ##STR230## A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-3 ##STR231## A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-3 ##STR232## A-6 O -- -- -- -- -- CH.sub.3 -- --L-4 ##STR233## A-2 O CH.sub.3 O -- -- -- -- -- --L-4 ##STR234## A-3 O OCH.sub.3 -- -- -- -- -- -- --L-4 ##STR235## A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-4 ##STR236## A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-4 ##STR237## A-6 O -- -- -- -- -- CH.sub.3 -- --L-5 ##STR238## A-2 O CH.sub.3 O -- -- -- -- -- --L-5 ##STR239## A-3 O OCH.sub.3 -- -- -- -- -- -- --L-5 ##STR240## A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-5 ##STR241## A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-5 ##STR242## A-6 O -- -- -- -- -- CH.sub.3 -- --L-6 ##STR243## A-2 O CH.sub.3 O -- -- -- -- -- --L-6 ##STR244## A-3 O OCH.sub.3 -- -- -- -- -- -- --L-6 ##STR245## A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-6 ##STR246## A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-6 ##STR247## A-6 O -- -- -- -- -- CH.sub.3 -- --L-2 CHCH.sub.2 A-2 O CH.sub.3 O -- -- -- -- -- --L-2 CHCH.sub.2 A-2 O OCH.sub.3 O -- -- -- -- -- --L-2 CHCH.sub. 2 A-2 O CH.sub.3 CH -- -- -- -- -- --L-2 CHCH.sub.2 A-3 O OCH.sub.3 -- -- -- -- -- -- --L-2 CHCH.sub.2 A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-2 CHCH.sub.2 A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-2 CHCH.sub.2 A-6 O -- -- -- -- -- CH.sub.3 -- --L-3 CHCH.sub.2 A-2 O CH.sub.3 O -- -- -- -- -- --L-3 CHCH.sub.2 A-3 O OCH.sub.3 -- -- -- -- -- -- --L-3 CHCH.sub.2 A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-3 CHCH.sub.2 A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-3 CHCH.sub.2 A-6 O -- -- -- -- -- CH.sub.3 -- --L-4 CHCH.sub.2 A-2 O CH.sub.3 O -- -- -- -- -- --L-4 CHCH.sub.2 A-3 O OCH.sub.3 -- -- -- -- -- -- --L-4 CHCH.sub.2 A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-4 CHCH.sub.2 A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-4 CHCH.sub.2 A-6 O -- -- -- -- -- CH.sub.3 -- --L-5 CHCH.sub.2 A-2 O CH.sub.3 O -- -- -- -- -- --L-5 CHCH.sub.2 A-3 O OCH.sub.3 -- -- -- -- -- -- --L-5 CHCH.sub.2 A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-5 CHCH.sub.2 A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-5 CHCH.sub.2 A-6 O -- -- -- -- -- CH.sub.3 -- --L-6 CHCH.sub.2 A-2 O CH.sub.3 O -- -- -- -- -- --L-6 CHCH.sub.2 A-3 O OCH.sub.3 -- -- -- -- -- -- --L-6 CHCH.sub.2 A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-6 CHCH.sub.2 A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-6 CHCH.sub.2 A-6 O -- -- -- -- -- CH.sub.3 -- --L-2 CHCH.sub.2 A-7 O -- -- -- -- -- -- CH.sub.3 OCH.sub.3L-2 CHCH.sub.2 A-7 O -- -- -- -- -- -- OCH.sub.3 OCH.sub.3L-2 CHCH.sub.2 A-7 O -- -- -- -- -- -- Cl OCH.sub.3L-2 CHCH.sub.2 A-7 O -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.3__________________________________________________________________________
TABLE Va__________________________________________________________________________General Structure VaL W A n X.sub.1 Y.sub.1 Y.sub.2 X.sub.2 Y.sub.3 X.sub.3 X.sub.4 Y.sub.4 m.p. (.degree.C.)__________________________________________________________________________L-2 ##STR248## A-2 O CH.sub.3 O -- -- -- -- - -L-2 ##STR249## A-2 O OCH.sub.3 O -- -- -- -- -- --L-2 ##STR250## A-2 O CH.sub.3 CH -- -- -- -- -- --L-2 ##STR251## A-3 O OCH.sub.3 -- -- -- -- -- -- --L-2 ##STR252## A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-2 ##STR253## A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-2 ##STR254## A-6 O -- -- -- -- -- CH.sub.3 -- --L-2 CHCH.sub.2 A-2 O CH.sub.3 O -- -- -- -- -- --L-2 CHCH.sub.2 A-2 O OCH.sub.3 O -- -- -- -- -- --L-2 CHCH.sub.2 A-2 O CH.sub.3 CH -- -- -- -- -- --L-2 CHCH.sub.2 A-3 O OCH.sub.3 -- -- -- -- -- -- --L-2 CHCH.sub.2 A-4 O OCH.sub.3 -- CH.sub.3 -- -- -- -- --L-2 CHCH.sub.2 A-5 O -- -- -- OCH.sub.3 CH.sub.3 -- -- --L-2 CHCH.sub.2 A-6 O -- -- -- -- -- CH.sub.3 -- --L-2 CHCH.sub.2 A-7 -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3L-2 CHCH.sub.2 A-7 -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3L-2 CHCH.sub.2 A-7 -- -- -- -- -- -- -- Cl OCH.sub.3__________________________________________________________________________
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 liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
______________________________________ Weight Percent* Active Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 3-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 0.1-95 5-99.9 0-15High Strength 90-99 0-10 0-2Compositions______________________________________ *Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
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 foaming, caking, corrosion, microbiological growth, etc.
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", 5th Ed., McGraw-Hill, New York, 1973, 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 6
______________________________________Wettable Powder______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methylpyrimidin- 80%2-yl)aminocarbonyl]-3-thiophenesulfonamidesodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 13%______________________________________
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
EXAMPLE 7
______________________________________Wettable Powder______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methyl- 50%1,3,5-triazin-2-yl)aminocarbonyl]-3-thiophene-sulfonamidesodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 46%______________________________________
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE 8
______________________________________Granule______________________________________Wettable Powder of Example 7 5%attapulgite granules 95%(U.S.S. 20-40 mesh; 0.84-0.42 mm)______________________________________
A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
EXAMPLE 9
______________________________________Extruded Pellet______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methylpyrimidin- 25%2-yl)aminocarbonyl]-3-thiophenesulfonamideanhydrous sodium sulfate 10%crude calcium ligninsulfonate 5%sodium alkylnaphthalenesulfonate 1%calcium/magnesium bentonite 59%______________________________________
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
EXAMPLE 10
______________________________________Oil Suspension______________________________________2-(1-cyclohexen-2-yl)-N--[(4-methoxy-6-methyl- 25%1,3,5-triazin-2-yl)aminocarbonyl]-3-thiophene-sulfonamidepolyoxyethylene sorbitol hexaoleate 5%highly aliphatic hydrocarbon oil 70%______________________________________
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
EXAMPLE 11
______________________________________Wettable Powder______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methylpyrimidin- 20%2-yl)aminocarbonyl]-3-thiophenesulfonamidesodium alkylnaphthalenesulfonate 4%sodium ligninsulfonate 4%low viscosity methyl cellulose 3%attapulgite 69%______________________________________
The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
EXAMPLE 12
______________________________________Low Strength Granule______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methyl- 1%1,3,5-triazin-2-yl)aminocarbonyl]-3-thiophene-sulfonamideN,N--dimethylformamide 9%attapulgite granules 90%(U.S.S. 20-40 sieve)______________________________________
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
EXAMPLE 13
______________________________________Aqueous Suspension______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methyl- 40%1,3,5-triazin-2-yl)aminocarbonyl]-3-thiophene-sulfonamidepolyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol ether 0.5%disodium phosphate 1%monosodium phosphate 0.5%polyvinyl alcohol 1.0%water 56.7%______________________________________
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
EXAMPLE 14
______________________________________Solution______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methylpyrimidin-2- 5%yl)aminocarbonyl]-3-thiophenesulfonamide, ammonium saltwater 95%______________________________________
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
EXAMPLE 15
______________________________________Low Strength Granule______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methylpyrimidin- 0.1%2-yl)aminocarbonyl]-3-thiophenesulfonamideattapulgite granules 99.9%(U.S.S. 20-40 mesh)______________________________________
The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
EXAMPLE 16
______________________________________Granule______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methyl- 80%1,3,5-triazin-2-yl)aminocarbonyl]-3-thiophene-sulfonamidewetting agent 1%crude ligninsulfonate salt (containing 10%5-20% of the natural sugars)attapulgite clay 9%______________________________________
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
EXAMPLE 17
______________________________________High Strength Concentrate______________________________________2-(1-cyclohexen-2-yl)-N--[4-methoxy-6-methylpyrimidin- 99%2-yl)aminocarbonyl]-3-thiophenesulfonamidesilica aerogel 0.5%synthetic amorphous silica 0.5%______________________________________
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
EXAMPLE 18
______________________________________Wettable Powder______________________________________N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocar- 90%bonyl]-1-methyl-4-(1-propenyl)-1H--pyrazole-5-sulfonamidedioctyl sodium sulfosuccinate 0.1%synthetic fine silica 9.9%______________________________________
The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.
EXAMPLE 19
______________________________________Wettable Powder______________________________________N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocar- 40%bonyl]-1-methyl-4-(1-propenyl)-1H--pyrazole-5-sulfonamidesodium ligninsulfonate 20%montmorillonite clay 40%______________________________________
The ingredient are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.
EXAMPLE 20
______________________________________Oil Suspension______________________________________N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocar- 35%bonyl]-1-methyl-4-(1-propenyl)-1H--pyrazole-5-sulfonamideblend of poly alcohol carboxylic 6%esters and oil soluble petroleumsulfonatesxylene 59%______________________________________
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
EXAMPLE 21
______________________________________Dust______________________________________N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocar- 10%bonyl]-1-methyl-4-(1-propenyl)-1H--pyrazole-5-sulfonamideattapulgite 10%Pyrophyllite 80%______________________________________
The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.
EXAMPLE 22
______________________________________Emulsifiable Concentrate______________________________________N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocar- 10%bonyl]-1-methyl-4-(1-propenyl)-1H--pyrazole-5-sulfonamidechlorobenzene 84%sorbitan monostearate and polyoxyethylene 6%condensates thereof______________________________________
The ingredients are combined and stirred to produce a solution which can be emulsified in water for application.
Utility
Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them 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. Some of the compounds have utility for selective weed control in crops such as rice and wheat. Alternatively, the subject compounds are useful to modify plant growth.
The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as 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 arount 0.05 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification 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.
The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.
Test A
Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), velvetleaf (Abutilon theophrasti), cheatgrass (Bromus secalinus), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliate leaf expanding, crabgrass, barnyardgrass and wild oats with two leaves, sicklepod with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, whereupon all species were compared to controls and visually rated for response to treatment. The ratings are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:
______________________________________ C = chlorosis or necrosis; B = burn; D = defoliation; E = emergence inhibition; G = growth retardation; H = formative effects; U = unusual pigmentation X = axillary stimulation; S = albinism; and 6Y = abscised buds or flowers.______________________________________
______________________________________CompoundsCompound R.sub.3 E X Y Z______________________________________ ##STR255##______________________________________ 1 H Se CH.sub.3 CH.sub.3 CH 2 H Se CH.sub.3 OCH.sub.3 CH 3 H Se OCH.sub.3 OCH.sub.3 CH 4 H Se CH.sub.3 CH.sub.3 N 5 H Se CH.sub.3 OCH.sub.3 N 6 H Se OCH.sub.3 OCH.sub.3 N 7 CH.sub.3 Se CH.sub.3 CH.sub.3 CH 8 CH.sub.3 Se CH.sub.3 OCH.sub.3 CH 9 CH.sub.3 Se OCH.sub.3 OCH.sub.3 CH10 CH.sub.3 Se CH.sub.3 CH.sub.3 N11 CH.sub.3 Se CH.sub.3 OCH.sub.3 N12 CH.sub.3 Se OCH.sub.3 OCH.sub.3 N13 H S CH.sub.3 CH.sub.3 CH14 H S OCH.sub.3 CH.sub.3 CH15 H S OCH.sub.3 OCH.sub.3 CH16 H S CH.sub.3 CH.sub.3 N17 H S OCH.sub.3 OCH.sub.3 N______________________________________ ##STR256##______________________________________18 OCH.sub.3 CH.sub.3 CH19 OCH.sub.3 OCH.sub.3 CH20 OCH.sub.3 OCH.sub.3 N______________________________________ ##STR257##______________________________________21 CH.sub.3 CH.sub.3 CH22 OCH.sub.3 CH.sub.3 CH23 OCH.sub.3 OCH.sub. 3 CH24 OCH.sub.3 CH.sub.3 N25 OCH.sub.3 OCH.sub.3 N26 Cl OCH.sub.3 CH______________________________________
TABLE A Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 Rate (kg/ha) 0.40 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0 .05 POSTEMERGENCE Morningglory 0 0 2C,6H 1C 0 2C 1C 6G 5C,8G 4C,9G 2C,7G 10C 9C Cocklebur 0 0 2G 1C,3G 3G 2C,8H 2C,4H 2C,8G 8G,9G 3C,8G 6G 4C,8G 7G Velvetleaf 2G 0 3C,8G 5C,9G 0 4C,9G 4C,8G 5C,9G 9C 10C 9C 9C 9C Nutsedge 0 0 2C,5G 5G 0 0 0 3C,7G 3C,8G 9C 0 0 0 Crabgrass 0 0 2G 0 0 0 0 2G 3G 0 0 3G 0 Barnyardgrass 4H 0 2C,7H 3C,8H 0 0 0 3C,9H 2C,9H 5C,9H 3C,5H 3C,8H 2C,5H Cheatgrass 0 0 5G 0 0 0 0 0 4G 4G 0 0 0 Wild Oats 0 0 2C,4G 0 0 0 0 3C,9G 2C,7G 0 0 0 0 Wheat 0 0 3G 0 0 0 0 6G 5G 0 0 0 0 Corn 2C,7H 0 3C,8G 0 0 2H 1H 2C,8G 3C,9G 3C,9H 9G 3C,8H 2C,8H Soybean 2H 0 3H,9G 4C,9G 0 2C,9G 7H 3C,9G 5C,9G 5C,9G 4C,9G 5C,9G 4C,9G Rice 6G 0 7G 8G 0 0 0 3C,9G 2C,8G 2C,8G 3C,9G 5G 0 Sorghum 2C,5H 0 3C,8G 7H 0 2G 0 2C,9G 3C,9H 3C,8H 2C,8H 4C,9H 2C,5H Sugar Beets 3C,6G 2H 2C,8G 9C 0 2C,5H 3C,5G 4C,9G 7G 9C 9C 9C 9C Cotton 3C,7H 0 3C,7H 2C,8G 0 3C,8H 3C,6H 4C,9G 4C,9G 5C,9G 9H 9C 9C PREEMERGENCE Morningglory 3G 0 8G 4G 0 2C 0 7G 9G 8G 2C 9G 9G Cocklebur 1H 0 7H 7G 0 2C 0 7G 9G 8H 5G -- 7H Velvetleaf 2G 0 8G 7G 0 2G 0 8G 10C 9C 8G 5C,9G 5C,9G Nutsedge 5G 0 0 7G 0 0 0 8G 9G 8G 0 0 0 Crabgrass 0 0 2G 0 0 0 0 2G 5G 3G 0 0 0 Barnyardgras s 0 0 2C,7G 4G 0 0 0 7H 9H 3C,9H 0 2C 1C Cheatgrass 5G 0 0 2G 0 0 0 9G 3C,9G 5C,9G 6G 0 0 Wild Oats 5G 0 2C,7G 0 0 0 0 8G 4C,9H 8G 2C,5G 2G 0 Wheat 4G 0 4G 0 0 0 0 8G 5C,9H 4G 0 0 0 Corn 2C,6H 2G 2C,8H 2C,8G 0 2G 0 2C,9G 5C,9H 8H 2C,7G 8G 5G Soybean 2C,2H 0 3C,7G 3C,6G 0 1C 0 3C,5H 2C,8G 7H 6G 8H 8H Rice 7H 0 7G 2C,7G 0 0 0 10E 10H 10E 8H 8G 5G Sorghum 7H 0 3C,9H 2C,7H 0 2G 0 5C,9H 10H 3C,8H 6G 3C,8H 3G Sugar Beets 3C,8G 0 2C,8G 8G 0 2C,6G 0 9C 10C 9C 9C 10C 10C Cotton 5G 0 7G 5G 0 6G 0 9G 9G 9G 6H 9G 9G Compound 13 Compound 14 Compound 16 Compound 17 Compound 18 Compound 19 Compound 20 Cmpd. 21 Cmpd. 22 Cmpd. 23 Cmpd.24 Cmpd. 25 Cmpd. 26 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 POSTEMERGENCE Morningglory 1H 4C,9G 3C,8H 1H 2C,7G 3C,8G 2C,7G 2H,5G 10C 9C 4C,8G 10C 10C 4C,9G Cocklebur 7H 4C,9G 3C,8H 0 2C 9C 9C 9H 2C,9H 9C 10C 9C 10C 10C Velvetleaf 8H 9C 10C 2C,7G 5C,9G 9C 4C,9G 8G 10C 9C 9G 10C 3C,8G 3C,8G Nutsedge 7G 3C,6G 5C,9G 0 0 3C,8G 2C,9G 0 0 5G 7G 0 3G 0 Crabgrass 2G 2C,5G 1C 0 0 3G 0 0 0 2G 0 0 0 0 Barnyardgrass 3H 4C,9H 3C,8H 0 0 3C,9H 4C,8H 0 6H 2C,6H 2H 1H 0 0 Cheatgrass 5G 2C,5G 0 0 0 6G 2G 0 5G 3G 5G 0 0 0 Wild Oats 0 3C,3H 0 0 0 0 2C 0 2C 0 0 0 0 0 Wheat 0 2G 0 0 0 2G 0 0 0 0 0 0 0 0 Corn 3H 3C,9H 2G 0 0 3C,9H 2C,9H 0 3C,8H 0 0 0 0 0 Soybean 0 3C,7H 3H,9G 1C,1H 2C,9G 4C,9H 3C,8H 2C,3H 3C,9G 4C,9G 5C,9G 9C 9C 2C,5G Rice 7G 8G 8G 5G 0 2C,6G 5G 0 3G 2G 2G 1G 0 0 Sorghum 2C,7G 3C,9G 2C,6G 2G 2C 4C,9H 3C,5G 3H 3C,8H 2C,8G 2C,6G 2C,6G 2G 2C,5G Sugar Beets 4C,9G 9C 9C 4C,8H 9C 4C,9H 2C,8G 3C,7G 2C,7G 4C,9G 9C 9C 9C 3H Cotton 4C,8H 9C 5C,9G 3C,4G 9H 9C 9C 2C,8G 9C 9C 9C 10C 10C 10C PREEMERGENCE Morningglory 5G 7G 6G 1H 5G 7H 9G 3C,7H 9G 9G 7G 9G 9G 6G Cocklebur 0 6G 2C,5G 0 3G 7H 7H 1C 8G 8H 8H 8G 8H 3H Velvetleaf 5G 8G 9G 0 5G 8G 8G 0 8G 8G 7G 8G 6G 3G Nutsedge 0 5G 5G 0 0 9G 10E 0 4G 8G 7G 0 0 0 Crabgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 1C 3C,7H 2C,2H 0 2C 6H 4G 0 3G 2C,7G 4G 0 0 0 Cheatgrass 0 5G 5G 0 0 6G 0 0 4G 8G 5G 0 0 0 Wild Oats 3G 2C,8G 0 0 0 1C 0 0 0 2C 0 0 0 0 Wheat 2G 5G 0 0 0 2G 5G 0 2G 0 0 0 0 0 Corn 2C,4G 2C,8G 3C,8H 0 0 9G 8G 2C,6G 5G 2C,5G 2C,2G 3G 2G 0 Soybean 2C,2H 3C,8H 6H 0 5H 8H 2C,3G 3C,3H 0 5G 2G 3G 0 0 Rice 2G 7H 3C,8H 0 3G 5G 5G 5G 7G 6G 2G 0 0 0 Sorghum 2C 3C,8H 3C,5G 0 0 2C,8G 2C,6H 2C,4G 4C,9G 2C,8H 3C,7H 3C,8G 3C,5G 2C,5G Sugar Beets 6G 9G 9G 0 4C,9G 9G 10C 4G 8G 4C,9G 2C,8G 4C,9G 9G 6G Cotton 4G 8G 8G 0 7G 9G 9G 7G 5G 8G 5G 9G 8G 5G
Claims
  • 1. A compound of the formula ##STR258## R is H or CH.sub.3 ; W.sub.3 is O or S;
  • n is 0 or 1;
  • E is S(O).sub.p or Se;
  • p is 0, 1 or 2;
  • R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CN, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl or CO.sub.2 R.sup.III ;
  • R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy;
  • R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or
  • R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
  • R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
  • R.sub.2 is C.sub.1 -C.sub.3 alkyl;
  • W is W.sub.1 or W.sub.2 ;
  • W.sub.1 is C.sub.2 -C.sub.8 alkenyl or C.sub.4 -C.sub.7 cycloalkenyl either of which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, amino, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, (C.sub.1 -C.sub.3 alkylamino)sulfamoyl, di(C.sub.1 -C.sub.3 alkylamino)sulfamoyl, OC(O)C.sub.1 -C.sub.3 alkyl, C(O)C.sub.1 -C.sub.3 alkoxy, OC(O)C.sub.1 -.sub.3 alkoxy, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.6 H.sub.5, OSO.sub.2 --4--CH.sub.3 -- C.sub.6 H.sub.4, phenyl or phenyl substituted with halogen, CH.sub.3, OCH.sub.3, SCH.sub.3 or NO.sub.2 ;
  • W.sub.2 is C.sub.2 alkynyl which may be substituted with phenyl or phenyl substituted with halogen, CH.sub.3, OCH.sub.3, SCH.sub.3 or NO.sub.2 or W.sub.2 is C.sub.3 -C.sub.8 alkynyl which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, (C.sub.1 -C.sub.3 alkylamino)sulfamoyl, di(C.sub.1 -C.sub.3 alkylamino)sulfamoyl, OC(O)C.sub.1 -C.sub.3 alkyl, OC(O)C.sub.1 -C.sub.3 alkoxy, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.6 H.sub.5, OSO.sub.2 --4--CH.sub.3 --C.sub.6 H.sub.4, phenyl or phenyl substituted with halogen, CH.sub.3, OCH.sub.3, SCH.sub.3 or NO.sub.2 ;
  • R.sub.3 is H or C.sub.1 -C.sub.4 alkyl; ##STR259## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino;
  • Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, ##STR260## m is 2 or 3; L.sub.1 and L.sub.2 are independently O or S;
  • R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl;
  • R.sub.6 is H or CH.sub.3 ;
  • Z is CH; and their agriculturally suitable salts;
  • provided that
  • (a) when X is Cl, F, Br or I, then Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
  • (b) when L is L-2 or L-3, then the W substituent and the sulfonylurea bridge are on adjacent carbon atoms;
  • (c) when W.sub.1 is C.sub.3 alkenyl, then L is L-3, L-4, L-5 or L-6;
  • (d) when L is L-1, then n is 1 and W is W.sub.2 ;
  • (e) when L is L-1 and W.sub.2 is C.sub.2 or C.sub.3 alkynyl, said group must be substituted;
  • (f) when W.sub.1 is C.sub.3 -C.sub.8 alkenyl or C.sub.4 -C.sub.7 cycloalkenyl substituted with OH, then the OH substituent is not bonded directly to the oelfinic group;
  • (g) when L is L-3, then the sulfonylurea bridge is bonded at the 3- or 5-position;
  • (h) when W.sub.3 is S, then R is H and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3 or CH(OCH.sub.3).sub.2 ;
  • (i) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R.sub.1 must be less than or equal to two and the number of carbons of W must be less than or equal to four; and
  • (j) when L is L-2, L-3, L-4 or L-5, then W.sub.1 is other than C.sub.2 -C.sub.8 alkenyl substituted with 1-3 atoms of F, Cl or Br.
  • 2. The compounds of claim 1 wherein R is H; and W.sub.3 is O.
  • 3. The compounds of claim 2 where R.sub.1 is H, F, Cl, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CH.sub.2 OCH.sub.3 or CH.sub.2 SCH.sub.3, and is not para to the sulfonylurea bridge.
  • 4. The compounds of claim 3 where X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3.
  • 5. The compounds of claim 4 where W.sub.1 is C.sub.2 -C.sub.5 alkenyl which may be optionally substituted by 1-3 atoms of F, Cl or Br, OH, OCH.sub.3, OC(O)CH.sub.3, OSO.sub.2 CH.sub.3, CN or SCH.sub.3, or W.sub.1 is C.sub.5 -C.sub.6 cycloalkenyl; and W.sub.2 is C.tbd.CC.sub.6 H.sub.5 or C.sub.3 -C.sub.5 alkynyl which may be optionally substituted by 1-3 atoms of F, Cl or Br, OH, OCH.sub.3, OC(O)CH.sub.3, CN or SCH.sub.3.
  • 6. The compounds of claim 5 where X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl or OCF.sub.2 H; Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2, OCF.sub.2 H, NHCH.sub.3, N(CH.sub.3).sub.2 or cyclopropyl; and R.sub.1 is H, CH.sub.3 OCH.sub.3 or Cl.
  • 7. The compounds of claim 6 where L is L-1.
  • 8. The compounds of claim 6 where L is L-2; and W is W.sub.1.
  • 9. The compounds of claim 6 where L is L-2; and W is W.sub.2.
  • 10. The compounds of claim 6 where L is L-3; and W is W.sub.1.
  • 11. The compounds of claim 6 where L is L-3; and W is W.sub.2.
  • 12. The compounds of claim 6 where L is L-4; and W is W.sub.1.
  • 13. The compounds of claim 6 where L is L-4; and W is W.sub.2.
  • 14. The compounds of claim 6 where L is L-5; and W is W.sub.1.
  • 15. The compounds of claim 6 where L is L-5; and W is W.sub.2.
  • 16. The compounds of claim 6 where L is L-6; and W is W.sub.1.
  • 17. The compounds of claim 6 where L is L-6; and W is W.sub.2.
  • 18. The compounds of claim 6 where L is L-7.
  • 19. The compound of claim 1 that is 2-(1-cyclohexen-2-yl)-N-[4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3-thiophenesulfonamide.
  • 20. The compound of claim 1 that is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(1-propenyl)-1H-pyrazole-5-sulfonamide.
  • 21. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
  • 22. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
  • 23. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
  • 24. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
  • 25. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
  • 26. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
  • 27. 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.
  • 28. 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.
  • 29. 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.
  • 30. 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.
  • 31. 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 5.
  • 32. 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 6.
RELATED APPLICATION

This is a continuation-in-part of application U.S. Ser. No. 768,158, filed Aug. 26, 1985 now abandoned which is a continuation-in-part of U.S. Ser. No. 680,549, filed Dec. 11, 1984, now abandoned.

US Referenced Citations (11)
Number Name Date Kind
4368069 Chen Jan 1983
4398939 Levitt Aug 1983
4420325 Sauers Dec 1983
4435206 Levitt Mar 1984
4481029 Levitt Nov 1984
4537618 Schurter et al. Aug 1985
4579583 Fory et al. Apr 1986
4594097 Schurter et al. Jun 1986
4620868 Kimurd et al. Nov 1986
4656273 Topfl Apr 1987
4743292 Hay et al. May 1988
Foreign Referenced Citations (5)
Number Date Country
59-152684 Jul 1984 JPX
833779 May 1983 ZAX
836449 Jul 1984 ZAX
842722 Oct 1984 ZAX
846610 Feb 1985 ZAX
Continuation in Parts (2)
Number Date Country
Parent 768158 Aug 1985
Parent 680549 Dec 1984