Phenyl-substituted sulfonamides

BACKGROUND OF THE INVENTION
This invention relates to novel condensed ring sulfonylureas and their use as herbicides and growth regulants.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR1## wherein R.sub.1 is ##STR2## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl;
R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;
R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms;
R.sub.8 is hydrogen, methyl, chlorine or bromine;
R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine;
W and Q are independently oxygen or sulfur;
n is 0, 1 or 2;
X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and
Y is methyl or methoxy; or their agriculturally suitable salts; provided that:
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen;
(b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and
(c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen.
U.S. Pat. No. 4,169,719 discloses herbicidal benezenesulfonylureas.
Herbicidal indanesulfonylureas are taught in U.S. Pat. No. 4,465,506.
Herbicidal quinolinesulfonylureas are described in U.S. Pat. No. 4,369,329, issued Jan. 18, 1983.
Herbicidal benzofuran, benzothiophene, benzopyran and benzothiopyran sulfonylureas are disclosed in EP-A-79,683, published May 25, 1983.
EP-A-82,681, published June 29, 1983, discloses herbicidal 1,3-benzodioxole and 1,4-benzodioxanesulfonylureas.
South African Patent Application 83/5165 discloses herbicidal sulfonylureas of the general structure shown below: ##STR3## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO.sub.2 -- group.
South African Patent Application 83/7434 discloses herbicidal sulfonamides of formula ##STR4## where Ar is ##STR5## and R.sub.2 is halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.6 alkoxyalkyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.
SUMMARY OF THE INVENTION
This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergent or postemergent herbicides or as plant growth regulants. ##STR6## wherein J is ##STR7## n is 0 or 1; W is O or S;
W.sub.1 is S;
W.sub.2 is O or S;
R is H or CH.sub.3 ;
R.sub.1 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, halogen, nitro, C.sub.1 -C.sub.6 alkoxy, SO.sub.2 NR.sub.a R.sub.b, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, CN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkylthio, NH.sub.2, C.sub.1 -C.sub.6 alkylamino, di(C.sub.1 -C.sub.6 alkyl)amino, Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), Si(CH.sub.3).sub.2 -phenyl or C.sub.1 -C.sub.3 alkyl substituted with 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, SO.sub.2 NR.sub.d R.sub.e, NO.sub.2, CN, CO.sub.2 R.sub.f, C.sub.1 -C.sub.3 haloalkoxy or C.sub.1 -C.sub.3 haloalkylthio;
R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 cyanoalkyl, methoxy or ethoxy;
R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or
R.sub.a and R.sub.b 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.sub.c 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.3 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.d is C.sub.1 -C.sub.3 alkyl;
R.sub.e is H or C.sub.1 -C.sub.3 alkyl;
R.sub.f is C.sub.1 -C.sub.3 alkyl;
R.sub.1 ' is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, halogen or NO.sub.2 ;
R.sub.2 is H, R.sub.11 ', SR.sub.11 ', SO.sub.2 R.sub.11, OR.sub.11 ', C(O)R.sub.11, C(O)OR.sub.11 ', (C(O)).sub.2 OR.sub.11 ', (CO).sub.2 R.sub.11 ', C(O)NR.sub.12 R.sub.18, C(O)NRA, C(S)SR.sub.11 ', NH.sub.2, NR.sub.12 R.sub.18, OH, CN, P(O)R.sub.13 R.sub.14, P(S)R.sub.13 R.sub.14, Si(CH.sub.3).sub.2 R.sub.15, L or C(O)L;
R.sub.3 is H or CH.sub.3 ;
R.sub.4 is C.sub.1 -C.sub.4 alkyl;
R.sub.5 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.6 is H or CH.sub.3 ;
R.sub.7 is C.sub.1 -C.sub.4 alkyl, Cl or Br;
A is ##STR8## 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, F, Cl, Br, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, amino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl;
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, azido, cyano, ##STR9## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3;
Q.sub.1 and Q.sub.2 are independently O or S;
R.sub.8 is H or C.sub.1 -C.sub.3 alkyl;
R.sub.9 and R.sub.10 are independently C.sub.1 -C.sub.3 alkyl;
Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr;
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;
X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ;
Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ;
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
Y.sub.3 is H or CH.sub.3 ;
Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl;
X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl;
R.sub.11 is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkoxyalkoxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.4 -C.sub.10 alkenylalkenyl, C.sub.3 -C.sub.10 epoxyalkyl, C.sub.2 -C.sub.10 alkynyl, C.sub.4 -C.sub.10 alkynylalkynyl, C.sub.4 -C.sub.10 alkynylalkenyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or ##STR10## when R.sub.11 is C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.7 cycloalkylalkyl it may optionally be substituted by C.sub.1 -C.sub.4 alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R.sub.11 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl or C.sub.2 -C.sub.10 alkynyl it may optionally be substituted by one or more halogens and/or by (R.sub.17).sub.m ', where when m' is 2, the values of R.sub.17 may be identical or different;
R.sub.11 ' is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkoxyalkoxyalkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.5 -C.sub.10 alkenylalkenyl, C.sub.3 -C.sub.10 epoxyalkyl, C.sub.3 -C.sub.10 alkynyl, C.sub.5 -C.sub.10 alkynylalkynyl, C.sub.5 -C.sub.10 alkynylalkenyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or ##STR11## when R.sub.1 ' is C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.7 cycloalkylalkyl it may be optionally substituted by C.sub.1 -C.sub.4 alkyl, 1 to 3 atoms of Cl or F or 1Br; when R.sub.11 ' is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl or C.sub.3 -C.sub.10 alkynyl, it may optionally be substituted by one or more halogens and/or by (R.sub.17).sub.m ', where when m' is 2, the values of R.sub.17 may be identical or different;
m' is 1 or 2;
R.sub.12 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.13 and R.sub.14 are independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio;
R.sub.15 is C.sub.1 -C.sub.10 alkyl, benzyl or ##STR12## R.sub.16 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, NO.sub.2, CN, SCH.sub.3, SO.sub.2 CH.sub.3 or CF.sub.3 ;
R.sub.17 is OR.sub.18, OC(O)R.sub.18, P+R.sub.9 R.sub.10 R.sub.15, P+(C.sub.6 H.sub.5).sub.3, OC(O)NR.sub.12 R.sub.18, OSO.sub.2 R.sub.18 ', OP(O)R.sub.13 R.sub.14, P(O)R.sub.13 R.sub.14 OP(S)R.sub.13 R.sub.14, P(S)R.sub.13 R.sub.14, OSi(CH.sub.3).sub.2 R.sub.15, Si(CH.sub.3).sub.2 R.sub.15, SR.sub.18, SOR.sub.18 ', SO.sub.2 R.sub.18 ', SCN, CN, SP(O)R.sub.13 R.sub.14, SP(S)R.sub.13 R.sub.14, N.sup.+ R.sub.12 R.sub.15 R.sub.18, NR.sub.12 R.sub.18, NR.sub.12 C(O)R.sub.18, NR.sub.12 C(O)OR.sub.18 ', NR.sub.12 C(O)NR.sub.12 R.sub.18, NR.sub.12 SO.sub.2 R.sub.18 ', NR.sub.12 P(O)R.sub.13 R.sub.14, NR.sub.12 P(S)R.sub.13 R.sub.14, NO.sub.2, C(O)R.sub.18, C(O)OR.sub.18, C(O)NR.sub.12 R.sub.18, SeR.sub.18, naphthyl, L, ##STR13## R.sub.18 is H, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl or ##STR14## R.sub.18 ' is C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl or ##STR15## R.sub.19 is H, F, Cl, Br, CH.sub.3, ##STR16## and L is a 5- or 6-membered aromatic heterocycle, a 5- or 6-membered dihydroaromatic heterocycle or a 5- or 6-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms wherein sulfur may take the form of S, SO or SO.sub.2, and/or 0-4 nitrogen atoms, with the proviso that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO.sub.2, and these heterocycles may optionally be substituted by 1-4 CH.sub.3, 1-2 OCH.sub.3, SCH.sub.3, Cl, N(CH.sub.3).sub.2 or CN or L is a 5- or 6-membered lactone, lactam or cycloalkanone which may optionally be substituted by 1-4 CH.sub.3 groups;
provided that
(a) when W is S, then R is H, J is J.sub.1, J.sub.2, J.sub.3 or J.sub.4 ; A is A-1, Z is CH or N, 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 CF.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR17## (b) when X is F, Cl or Br, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
(c) when R.sub.3 is CH.sub.3, then n is O;
(d) when J is J-1 or J-2 and R.sub.2 is H or C.sub.1 -C.sub.4 alkyl, then R.sub.1 and R.sub.1 ' are other than H, F, Cl, Br, CH.sub.3, OCH.sub.3, CF.sub.3, OCF.sub.2 H, or SCH.sub.3 or X is other than CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, OCF.sub.2 H, CH.sub.2 Cl, CH.sub.2 Br, CH.sub.2 F, cyclopropyl or CF.sub.3 or Y is C.sub.3 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkoxy, C.sub.4 haloalkoxy, C.sub.4 haloalkylthio, C.sub.3 -C.sub.5 alkoxyalkyl, C.sub.4 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.3 alkylamino, di(C.sub.2 -C.sub.3 alkyl)amino, C.sub.4 alkenyloxy, C.sub.4 alkynyloxy, C.sub.3 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C(O)R.sub.8 or N(OCH.sub.3)CH.sub.3 ;
(e) the total number of carbon atoms in R.sub.2 does not exceed 13;
(f) when X is C.sub.3 -C.sub.5 cycloalkyl, then Y is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, OCF.sub.2 H, SCF.sub.2 H, OCH.sub.2 CF.sub.3, CF.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, NHCH.sub.3, N(CH.sub.3).sub.2 or CH(OCH.sub.3).sub.2 ;
(g) when R.sub.1 or R.sub.1 ' is para to the sulfonylurea bridge then R.sub.1 or R.sub.1 ' are H, CH.sub.3, F, Cl, Br or OCH.sub.3 ; and
(h) when X or Y is OCH.sub.2 CH.sub.2 F or OCH.sub.2 CHF.sub.2 then R.sub.2 is other than C.sub.5 alkyl, CH.sub.3 OCH.sub.2 CH.sub.2, C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 or C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br;
(i) when X is Y is OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2 or OCH.sub.2 CF.sub.3, then the other is not di(C.sub.1 -C.sub.3 alkyl)amino C.sub.1 -C.sub.3 alkylamino or N(OCH.sub.3)CH.sub.3 ;
(j) when X or Y is OCF.sub.2 H, then Z is CH;
(k) when R.sub.17 and the bridging nitrogen of a cyclic sulfonamide are attached to the same carbon, then R.sub.17 is other than OH, SH, OC(O)R.sub.18, OC(O)NR.sub.12 R.sub.18, OSO.sub.2 R.sub.18 ', OP(O)R.sub.13 R.sub.14, OSi(CH.sub.3).sub.2 R.sub.15, SP(O)R.sub.13 R.sub.14, SP(S)R.sub.13 R.sub.14, NR.sub.12 R.sub.18 or N+R.sub.12 R.sub.15 R.sub.18 ;
and their agriculturally suitable salts.
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, 2-propyl or the different butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl isomers.
Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butyl, pentyl or hexyl isomers.
Alkenyl denotes straight chain or branched alkenes, e.g. vinyl, 1-propenyl, 2-propenyl, isopropenyl and the different butenyl, pentenyl, hexenyl, heptenyl, ocetenyl, nonenyl or decenyl isomers.
Alkynyl denotes straight chain or branched alkynes, e.g. ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl and decynyl isomers.
Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the different propylsulfonyl isomers.
Alkylthio, alkylsulfinyl, alkylamino, alkylsulfamoyl, etc. are defined analogously to the above examples.
Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine.
The total number of carbon atoms in a substituent group is indicated by the C.sub.i -C.sub.j prefix where i and j are numbers from 1 to 10. For example, C.sub.3 -C.sub.5 alkylthioalkyl would designate CH.sub.2 SCH.sub.2 CH.sub.3 through (CH.sub.2).sub.4 SCH.sub.3 or CH.sub.2 SC.sub.4 H.sub.9, C.sub.2 alkoxyalkoxy would designate OCH.sub.2 OCH.sub.3, C.sub.2 cyanoalkyl would designate CH.sub.2 CN and C.sub.3 cyanoalkyl would designate CH.sub.2 CH.sub.2 CN and CH(CN)CH.sub.3.
It would be recognized by one skilled in the art that when R.sub.17 is OH or SH, that these substituents cannot be bonded to the same carbon as another heteroatom or to an olefinic or acetylenic carbon atom.
Preferred for reasons of their higher herbicidal activity, greater plant growth regulant activity or more favorable ease of synthesis are:
1. Compounds of Formula I wherein J is J-1 or J-4.
2. Compounds of Formula I wherein J is J-2 or J-3.
3. Compounds of Formula I wherein J is J-8 or J-9.
4. Compounds of Formula I wherein J is J-5, J-6, J-7 or J-10.
5. Compounds of Formula I wherein J is J-11 or J-12.
6. Compounds of Preferred 1 wherein
W is O;
R is H;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F, CF.sub.3 or cyclopropyl;
Y is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, 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 CF.sub.3, CN, N.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR18## or QCF.sub.2 T; Q is O or S;
T is H, CHClF CHBrF or CHFCF.sub.3.
7. Compounds of Preferred 6 wherein R.sub.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, amino, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CN, NH.sub.2, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkylamino) or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 haloalkylthio, CN or NO.sub.2.
8. Compounds of Preferred 7 wherein
R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkylcarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkyl substituted by 1-3 atoms of F, Cl or 1 Br, or by 1 or 2 groups selected from C.sub.1 -C.sub.2 alkoxy, CN, C.sub.1 -C.sub.2 alkoxycarbonyl, C.sub.1 -C.sub.2 alkylcarbonyl, OH, C.sub.1 -C.sub.2 alkylthio C.sub.1 -C.sub.2 alkylsulfonyl, C.sub.1 -C.sub.2 alkylsulfonyloxy or C.sub.1 -C.sub.2 alkylcarbonyloxy, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.4 alkynyl substituted by 1 atom of F or Cl, phenyl or phenyl substituted with Cl, CF.sub.3, NO.sub.2, CN or SO.sub.2 CH.sub.3 ; and
R.sub.4 is CH.sub.3.
9. Compounds of Preferred 8 wherein
A is A-1; and
Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, OCF.sub.2 H or CH(OCH.sub.3).sub.2.
10. Compounds of Preferred 9 wherein R.sub.1 and R.sub.1 ' are H, Cl, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio.
11. Compounds of Preferred 10 wherein J is J-1.
12. Compounds of Preferred 11 wherein
R.sub.1 is H; and
Z is CH.
13. Compounds of Preferred 12 wherein R.sub.2 is C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.3 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfonyl or CN, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.3 alkoxycarbonyl or C.sub.1 -C.sub.3 alkylcarbonyl.
14. Compounds of Preferred 11 wherein
R.sub.1 is H;
Z is N; and
R.sub.2 is C.sub.1 -C.sub.3 alkylcarbonyl or C.sub.1 -C.sub.3 alkoxycarbonyl.
15. Compounds of Preferred 2 wherein
W is O;
R.sub.1 is H;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F, CF.sub.3 or cyclopropyl;
Y is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, 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 CF.sub.3, CN, N.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR19## or QCF.sub.2 T; R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkylcarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkyl substituted by 1-3 atoms of F, Cl or 1 Br, or by 1 or 2 groups selected from C.sub.1 -C.sub.2 alkoxy, CN, C.sub.1 -C.sub.2 alkoxycarbonyl, C.sub.1 -C.sub.2 alkylcarbonyl, OH, C.sub.1 -C.sub.2 alkylthio C.sub.1 -C.sub.2 alkylsulfonyl, C.sub.1 -C.sub.2 alkylsulfonyloxy or C.sub.1 -C.sub.2 alkylcarbonyloxy, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.4 alkynyl substituted by 1 atom of F or Cl, phenyl or phenyl substituted with Cl, CF.sub.3, NO.sub.2, CN or SO.sub.2 CH.sub.3 ;
R.sub.1 ' is H, Cl, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio.
16. Compounds of Preferred 15 wherein
A is A-1; and
Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, OCF.sub.2 H or CH(OCH.sub.3).sub.2.
17. Compounds of Preferred 3 wherein
W is O;
R.sub.1 is H;
R.sub.1 ' is H;
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F or cyclopropyl; and
Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, OCF.sub.2 H or CH(OCH.sub.3).sub.2 ;
18. Compounds of Preferred 4 wherein
W is O;
R.sub.1 is H;
R.sub.1 ' is H;
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F or cyclopropyl; and
Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, OCF.sub.2 H or CH(OCH.sub.3).sub.2 ;
19. Compounds of Preferred 5 wherein
W is O;
R.sub.1 is H;
R.sub.1 ' is H;
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F or cyclopropyl; and
Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, OCF.sub.2 H or CH(OCH.sub.3).sub.2.
Specifically preferred for reasons of their highest herbicidal activity, greatest plant growth regulant activity and/or most favorable ease of synthesis are:
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-methoxyethyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 194.degree.-197.degree. C.;
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(3-methylbutyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 227.degree.-229.degree. C.;
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(phenylmethyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 216.degree.-218.degree. C.;
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-oxopropyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 178.degree.-182.degree. C.;
2,3-dihydro-N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(2-ethoxyethyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 193.degree.-197.degree. C.;
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-ethoxyethyl)-1,2-benzisothiazole-7-sulfonamide, 1-1-dioxide, m.p. 203.degree.-204.degree. C.;
2,3-dihydro-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(2-fluoroethyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 214.degree.-215.degree. C.;
2,3-dihydro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-fluoroethyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 190.degree.-192.degree. C.;
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-acetyl-1,2-benzoisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 191.degree.-193.degree. C.;
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(3-chloropropyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 201.degree.-203.degree. C.;
2,3-dihydro-N-[(chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(2-fluoroethyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 215.degree.-217.degree. C.;
2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(3-fluoropropyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 199.degree.-200.degree. C.;
2,3-dihydro-N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(2-chloroethyl)-1,2-benzisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 219.degree.-220.degree. C.;
N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(2-fluoroethyl)-2,3-dihydro-1,2-benzoisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 215.degree.-217.degree. C.;
N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(3-fluoropropyl)-2,3-dihydro-1,2-benzoisothiazole-7-sulfonamide, 1,1-dioxide, m.p. 222.5.degree.-223.5.degree. C.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The following discussion represents a general outline for the preparation of the compounds of this invention. All of the syntheses described below are multistep with one or more methods being taught for each step. This allows for a wide variety of possible synthetic pathways to prepare a particular compound of Formula I. The proper choice of the synthetic pathway and the best ordering of the reaction sequences for each individual compound will be known to one skilled in the art.
The compounds of Formula I can be prepared by one or more of the methods described below in Equations 1 through 5.
As shown in Equation 1, many of the compounds of Formula I, where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4, can be prepared by reacting a sulfonylisocyanate (W=O) or, a sulfonylisothiocyanate (W=S) of Formula II with an appropriate heterocyclic amine of Formula III. R, A and W are as previously defined. ##STR20##
The reaction is carried out at 25.degree. to 100.degree. C. in an inert, aprotic solvent such as methylene chloride or xylene for 0.5 to 24 hours as taught in U.S. Pat. No. 4,127,405.
Many of the compounds of Formula I, where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4, W is S and R is H, (Ia) can be prepared by reacting the appropriate sulfonamide of Formula IV with a heterocyclic isothiocyanate of Formula V, as shown in Equation 2. ##STR21##
The reaction is carried out at 25.degree. to 80.degree. C. in an inert, aprotic solvent such as acetone or acetonitrile in the presence of a base such as potassium carbonate for 0.5 to 24 hours. The required heterocyclic isothiocyanates V are prepared from the corresponding amines III which would be known to one skilled in the art as taught in EPO Publication 35,893.
Many of the compounds of Formula I, where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4 and W is O (Ib), can be prepared by reacting a sulfonylcarbamate of Formula VI with an appropriate amine of Formula III, as shown in Equation 3. ##STR22##
The reaction is carried out at 50.degree. to 100.degree. C. in a solvent such as dioxane for 0.5 to 24 hours. The required carbamates VII are prepared by reacting the corresponding sulfonamides IV with diphenylcarbonate in the presence of a strong base.
Compounds of Formula Ib can also be prepared, as shown in Equation 4, by reacting a heterocyclic carbamate of Formula VII with an appropriate sulfonamide of Formula IV. ##STR23##
The reaction is carried out at 0.degree. to 50.degree. C. in a solvent such as acetonitrile or dioxane in the presence of a non-nucleophilic base such as DBU for 0.2 to 24 hours. The required phenylcarbamate VII are prepared by reacting the corresponding heterocyclic amines III with diphenylcarbonate or phenylchloroformate in the presence of a strong base.
Many of the compounds of Formula Ib where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4 can be prepared by reacting the sulfonamides of Formula IV with an appropriate methylcarbamate of Formula VIII in the presence of an equimolar amount of trimethylaluminum, as shown in Equation 5. ##STR24##
The reaction is carried out at 25.degree. to 40.degree. C. in a solvent such as methylene chloride for 10 to 96 hours under an inert atmosphere. The required carbamates VIII are prepared by reacting the corresponding amines III with dimethylcarbonate or methyl chloroformate in the presence of a strong base.
The intermediate sulfonylisocyanates (W=O) and sulfonylisothiocyanates (W=S) of Formula II from Equation 1 can be prepared as shown in Equations 4 through 8.
As shown in Equation 6, many of the sulfonylisocyanates of Formula IIa where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4 can be prepared by the reaction of sulfonamides of Formula IV with phosgene, in the presence of n-butylisocyanate and a tertiary amine catalyst, at reflux in a solvent such as xylene by the method of U.S. Pat. No. 4,238,621. ##STR25##
The sulfonylisocyanates can also be prepared from the sulfonamides by a two step procedure involving (a) reacting the sulfonamides with n-butylisocyanate in the presence of a base such as K.sub.2 CO.sub.3 at reflux in an inert solvent such as 2-butanone forming a n-butylsulfonylurea; and (b) reacting this compound with phosgene and a tertiary amine catalyst at reflux in xylene solvent. The method is similar to a procedure taught by Ulrich and Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed.
Alternatively, as shown in Equation 7, many of the sulfonylisocyanates of Formula IIa where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4 can be prepared by reacting the corresponding sulfonyl chlorides IX with cyanic acid salts. ##STR26##
The reaction is carried out at 25.degree. to 100.degree. C. in an inert aprotic solvent such as acetonitrile for 0.5-24 hours in the presence of phosphorus pentoxide and an alkali metal salt such as lithium iodide.
Many of the sulfonylisothiocyanates of Formula IIb where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4 can be prepared, as shown in Equation 8, by contacting the sulfonamides of Formula IV with carbon disulfide in the presence of two equivalents of a strong base. The resulting salt is then reacted with phosgene according to the teachings of K. Hartke, Arch. Pharm., 299, 174 (1966). ##STR27##
The sulfonamides of Formula IV where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4 of Equations 2, 4, 5, 6 and 8 as well as the other sulfonamides required to prepare the compounds of this invention can be prepared from the corresponding sulfonyl chlorides of Formula IX by contacting with either anhydrous or aqueous ammonia as shown in Equation 9. ##STR28##
The preparation of sulfonamides from sulfonyl chlorides is widely reported in the literature, for reviews see: F. Hawking and J. S. Lawrence, "The Sulfonamides," H. K. Lewis and Co., London, 1950 and E. H. Northey, "The Sulfonamides and Allied Compounds," Reinhold Publishing Corp., New York, 1948.
Alternatively, many sulfonamides IV can be prepared by dealkylation of their corresponding N-t-butyl sulfonamides X as shown in Equation 10. ##STR29##
The reaction is carried out by contacting the N-t-butyl sulfonamide X with a strong acid such as trifluoroacetic acid or methanolic HCl at 25.degree. to 50.degree. C. for 0.5 to 24 hours. The N-t-butyl sulfonamides X are readily prepared by reacting sulfonylchlorides IX with t-butylamine and are useful either as an aid in purification, to enhance solubility for subsequent reactions such as Equation 12 below or to protect the sulfonamide function from competing with reactions at other parts of the molecule.
Many of the sulfonamides of Formula IVa can be prepared by functionalization of the corresponding N-unsubstituted sulfonamides of Formula IVb as shown in Equation 11. G.sub.1 -G.sub.2 is CHR.sub.3 (CHR.sub.4).sub.n and CH.dbd.CR.sub.4, R' is H or C(CH.sub.3).sub.3 and X is Cl, Br, I or other readily displaceable groups. When R.sub.3 is CH.sub.3 then is 0. ##STR30##
The reaction is carried out by contacting the sulfonamides IVb with the appropriate electrophile in the presence of a suitable base such as K.sub.2 CO.sub.3 in an inert, polar solvent such as DMF at 0.degree. to 100.degree. C. for 0.5 to 24 hours. In some instances the R.sub.2 function can also be introduced by Michael addition of IVb to the appropriate Michael acceptor as known to one skilled in the art.
While many of the R.sub.2 groups can be introduced directly, as described above, some of the R.sub.2 groups may best be prepared by standard functional group manipulations upon compounds of Formula IVa containing an appropriate R.sub.2 group pecursor as will be known to one skilled in the art. Some examples of these manipulations are the preparation of IVa where R.sub.2 contains an epoxide by the epoxidation of IVa where R.sub.2 contains a carbon-carbon double bond, the preparation of IVa where R.sub.2 contains a sulfone by the oxidation of IVa where R.sub.2 contains a thioether function, the preparation of IVa where R.sub.2 contains OC(O)CH.sub.3 by acetylation of IVa where R.sub.2 contains OH, or the preparation of IVa where R.sub.2 contains NH.sub.2 by the reduction of IVa where R.sub.2 contains NO.sub.2. This is also the case for many of the R.sub.1 substituents which can be prepared by an analogous chemical manipulation known to one skilled in the art.
Many of the unsaturated sulfonamides of Formula IVc can also be prepared from the corresponding saturated sulfonamides of Formula IVd by the two-step procedure shown in Equation 12. G.sub.1 -G.sub.2 is SO.sub.2 --NR.sub.2, CO--NR.sub.5 or NR.sub.5 --CO, R' is H or C(CH.sub.3).sub.3 and R" is H or R.sub.4. ##STR31##
The first step involves benzylic bromination by N-bromosuccinimide to give a monobromide which is subsequently dehydrobrominated in a second step by reaction with a suitable base such as triethyl amine or potassium-t-butoxide in an inert solvent such as THF. This method has been used to prepare isocoumarins from 3,4-dihydroisocoumarins, see R. Barry, Chem. Rev., 64, 229 (1964). In cases where R.sub.1 is an alkyl group, competitive bromination at this site may occur resulting in a mixture. The desired bromide may be separated at this stage, or after treatment with the base, by standard methods.
The thiocarbonylsulfonamides of Formula IV where J is J.sub.5, J.sub.6, J.sub.7, J.sub.8, J.sub.9 and J.sub.10 and where W.sub.1 is S can be prepared from their corresponding oxygen analogs where W.sub.1 is O as represented in Equation 13 using ring system J.sub.5 as an example. ##STR32##
The reaction is carried out at 100.degree. to 140.degree. C. in a solvent such as xylene for 1.0 to 24 hours as taught by Lawesson, et al. Bull. Chem. Soc. Belg., 87, 229 (1978). The corresponding oxygen carbonyl sulfonamides of ring systems J.sub.5, J.sub.6, J.sub.7, J.sub.8, J.sub.9 and J.sub.10 where W.sub.1 is O can be prepared according to the methods described herein and in EPO Publication No. 107979. EPO Publication No. 107979 also describes the synthesis of indanone and tetralone sulfonamides which can be ketalized by standard methods known to one skilled in the art to give sulfonamides of Formula IV where J is J-11 and J-12.
The sulfonyl chlorides of Formula IX of Equations 7 and 9 are important intermediates for the preparation of the compounds of this invention. The syntheses of the required sulfonyl chloride intermediates where J is J.sub.1, J.sub.2, J.sub.3 and J.sub.4 are described in Equations 14 through 16. These methods can also be used to prepare the corresponding oxygen carbonyl analogs of ring systems J.sub.5, J.sub.6, J.sub.7, J.sub.8, J.sub.9 and J.sub.10 where W.sub.1 is O.
As shown in Equation 14, many of the sulfonyl chlorides of Formula IX can be prepared from the corresponding amines XI. ##STR33##
The reaction involves diazotization of the amine XI with sodium nitrite in HCl, followed by reaction of the diazonium salt with sulfur dioxide and cupric chloride in acetic acid analogous to the teachings of Yale and Sowinski, J. Org. Chem., 25, 1824 (1960).
Alternatively, sulfonyl chlorides of Formula IX can be prepared by a modification of the above procedure whereby the diazotization reaction is carried out in dilute sulfuric acid and the resulting diazonium salt is reacted with sulfur dioxide, HCl and cupric chloride in a cosolvent mixture consisting of acetic acid-water (1:1) and an immiscible, inert solvent such as 1-chlorobutane or methylene chloride at 0.degree.-40.degree. C. for 1 to 24 hours.
Many of the sulfonyl chlorides of Formula IX can also be prepared by oxidative chlorination of the corresponding thio compounds of Formula XII as shown in Equation 15. R' is H, alkyl, benzyl or carbamoyl, R.sub.1 is not SCH.sub.3 and J does not contain non-aromatic unsaturation. ##STR34##
The reaction is carried out by addition of molecular chlorine or a chlorine equivalent to the thio compound in the presence of water at 0.degree. to 80.degree. C. in an aliphatic carboxylic acid solvent such as acetic acid or an inert organic solvent such as dichloroethane for 1 to 24 hours.
Alternatively, many of the sulfonyl chlorides of Formula IX can be prepared by the two-step sequence shown in Equation 16 starting from the thio compounds XII where R' is H (XIIa) and R.sub.1 is not SCH.sub.3. ##STR35##
The thiol XII (R'=H) is contacted with excess hydrogen peroxide in the presence of base to give a sulfonic acid salt which in turn is converted to the desired sulfonyl chloride by contacting with a suitable reagent such as thionyl chloride or phosphorous pentachloride as known to one skilled in the art.
Some of the sulfonyl chlorides of Formula IX may best be prepared by direct chlorosulfonation depending on the substitution pattern on the ring and the nature of the substituent as will be known to one skilled in the art.
Many of the S-arylthiocarbamates of Formula XIIb (XII, R'=CON(CH.sub.3).sub.2) can be prepared by the Newman-Kwart rearrangement starting with the corresponding phenols XIII as shown in Equation 17. ##STR36##
The phenol XIII is first reacted with N,N-dimethylthiocarbamoyl chloride in the presence of a base. The resulting O-aryl-N,N-dimethylthiocarbamate XIV is then heated at 150.degree. C. to 300.degree. C. for 2 to 24 hours as taught by Newman and Karnes J. Org. Chem., 31, 3980 (1966) to give the desired S-aryl-N,N-dimethylthiocarbamate XIIb. The related thiols XIIa can be obtained by hydrolysis of the thiocarbamates XIIb.
Many of the sulfides of Formula XII where R' is alkyl or benzyl can be prepared by reacting a halocompound of Formula XV with an appropriate mercaptan in the presence of a base as shown in Equation 18. R' is alkyl or benzyl and X is F, Cl or Br. ##STR37##
The reaction is carried out in a solvent such as DMF at 25.degree. to 150.degree. C. for 0.5 to 24 hours. The halocompounds XV must not contain functionality which can be attacked by a mercaptide anion as will be known to one skilled in the art. An example of this would be where J is J.sub.1 and R.sub.2 was a haloalkyl group. These compounds can be prepared from the corresponding sulfides XII where J is J.sub.1, R' is alkyl or benzyl and R.sub.2 is H by standard alkylation methods.
Many of the thiocompounds XII of Equation 15 and the chlorocompounds XV (X=Cl) of Equation 18, where J is J.sub.1 and n is O, can be prepared by the reaction sequence shown in Equation 19. G is Cl or S-alkyl, R.sub.1 does not contain functionality incompatible with BuLi or BH.sub.3 and R.sub.3 is as previously defined. ##STR38##
The sequence begins by contacting an appropriately substituted N-t-butylbenzenesulfonamide XVI with two equivalents of butyl lithium at 0.degree. to 25.degree. C. in an inert solvent such as THF for 2 to 10 hours to give a dianion according to the teachings of J. Lombardino, J. Org. Chem., 36, 1843 (1971). The dianion can then be trapped with an ester or, when R.sub.3 is H, with dimethylformamide at -78.degree. to 25.degree. C. to produce, upon aqueous acid workup, the hemiaminal XVII. The hemiaminal XVII can be de-t-butylated and dehydrated by a catalytic amount of acid such as p-toluene-sulfonic acid in a solvent such as benzene or toluene at reflux. The resulting benzisothiazole XVIII can be reduced with a reagent such as sodium borohydride in a suitable solvent such as ethanol to produce a 2,3-dihydrobenzisothiazole which is N-alkylated as described in equation II to give either XII (J=J.sub.1, R'=alkyl) or XV (J=J.sub.1, X=Cl) by standard methods known to one skilled in the art. Alternatively, hemiaminal XVII may be treated with diborane to produce a t-butyl-2,3-dihydrobenzisothiazole XVIIIa. Compounds XII (J=J.sub.1, R'=alkyl) or XV (J=J.sub.1, X=Cl) are then readily prepared as described previously by treatment of XVIIIa with trifluoroacetic acid followed by N-alkylation. If the t-butyl group in structures XVI and XVII is replaced by the appropriate R.sub.2 group, the diborane reduction of the hemiaminal gives XII and XV directly.
Many of the thio compounds XII of Equation 15 and the chloro compounds XV of Equation 18, where J is J.sub.1 and J.sub.4 and n=1, can be prepared by the reaction sequence shown in Equation 20. G is Cl or S-alkyl, Y is H or CH.sub.3, R.sub.1 does not contain functionality incompatible with BuLi. R" is C(CH.sub.3).sub.3 or functionality selected from R.sub.2 which is compatible with the lithiation conditions shown as will be known to one skilled in the art and R.sub.4 is H or C.sub.1 -C.sub.4 alkyl. ##STR39##
The reaction is carried out by reacting the N-substituted benzenesulfonamides XIX with two equivalents of n-BuLi at -78.degree. to 25.degree. C. in a solvent such as THF for 0.5 to 5 hours. When Y is H, an ortho-anion is formed which is trapped with an appropriate epoxide to give the hydroxy sulfonamides XX. When Y is CH.sub.3, an ortho-methyl anion is produced which is reacted with an aldehyde or DMF to give alcohol XX. The alcohol can be mesylated by reaction of XX with mesyl chloride in the presence of an equivalent of a tertiary amine at 0.degree. to 25.degree. C. for 1 to 24 hours in a solvent such as methylene chloride. The resulting mesylate is cyclized by heating with a base such as potassium carbonate in a solvent such as DMF to produce the desired compounds XII (J=J.sub.1, J.sub.4, R'=alkyl) or XV (J=J.sub.1, J.sub.4, X=Cl). When R" is C(CH.sub.3).sub.3, contacting with acid as described in Equation 10 will give the corresponding benzisothiazine where R" is H. This can be alkylated as described previously for the benzisothiazoles of Equation 19.
Many of the thio compounds of Formula XII, where J is J.sub.6 or J.sub.10 (W.sub.1 =O), can be prepared from the thioether compounds XXI shown in Equation 21. Y is H or CH.sub.3, R.sub.1 ' does not contain Br, R' is C.sub.2 -C.sub.4 alkyl, R.sub.6 is H or CH.sub.3 and R.sub.7 is H or C.sub.1 -C.sub.4 alkyl. ##STR40##
The reaction is carried out by reacting the N-methylcarboxamide XXI with two equivalents of n-BuLi at -78.degree. to 25.degree. C. in a solvent such as THF for 0.5 to 5 hours to give, when Y is H, an orthoanion which is trapped with an appropriate epoxide to give the hydroxy sulfonamides XXII as taught by Narasimkan and Bhide, Chem. Comm., 1552 (1970). When Y is CH.sub.3, an ortho methyl anion is produced which is reacted with an aldehyde or slowly enolizable ketones to give the amides XXII as taught by Watanabe et al. Tetrahedron Lett. 1647 (1982). The amides XXII are saponified by standard methods to the corresponding benzoic acids which readily cyclize upon heating in the presence of acid such as p-toluenesulfonic acid to give the desired lactones XII (J=J.sub.6, J.sub.10, R'=alkyl).
The amines of Formula XI in Equation 14, can be prepared by reduction of the corresponding nitro compounds of Formula XXI, as shown in Equation 22. ##STR41##
The reduction of nitro compounds to amines can be carried out by any of several known methods as described in Preparative Organic Chemistry, 4 Ed., p. 557-563, John Wiley and Sons, New York and London, G. Hilgetag and A. Martini Ed.
Many of the nitro compounds of Formula XXIII in Equation 22 can be prepared by the procedures outlined in Equations 23 through 30. With suitable modifications known to one skilled in the art, the general ring forming reactions outlined below for these nitro compounds XXIII can be adapted to prepare many of the phenols of Formula XIII and halocompounds of Formula XV.
As shown in Equation 23, many of the nitro compounds of Formula XXI, where J is J.sub.1 (XXIIIa) can be prepared starting from the appropriately substituted nitrobenzenes of Formula XXII. R' is H or CH.sub.2 Cl. ##STR42##
The nitrobenzenes XXIV are first reduced to their corresponding amines and nitrated by standard methods to produce, in part, compounds of Formula XXV. In some instances, it may be desirable to first protect the amino group as its acetate prior to nitration as is known to one skilled in the art. The desired nitro compound XXV can be isolated by either fractional crystallization or chromatographic procedures and converted to sulfonyl chlorides XXVI by the method previously discussed in Equation 14. The intermediate sulfonyl chlorides XXVI can be converted into their corresponding sulfonamides by reaction with an appropriate amine (see Equation 9) and subsequently cyclized: (a) when R' is CH.sub.2 Cl, to the nitro-1,2-benzothiazines XXIIIa, where n is 1, by heating in the presence of a base such as potassium carbonate; or (b) when R' is H, by contacting the sulfonamide with NBS in a solvent such as carbon tetrachloride to give sulfonamides where R' is Br, followed by contacting this product with a base to give the nitro benzisothiazoles XXIa where n is 0. Note the discussion of Equation 12 for NBS brominations when R.sub.1 is alkyl.
The procedure of Equation 23 is similar to the method taught by E. Sianesi et al., Chem. Ber., 104, 1880 (1971) for the preparation of substituted 1,2-benzothiazine-1,1-dioxides. The starting nitrobenzenes XXII can be prepared by standard methods known to one skilled in the art.
Alternatively, as shown in Equation 24, many of the nitro compounds of Formula XXIIIa where n is 1 can be prepared, in part, by contacting the nitro acetamides XXVII with fuming sulfuric acid according to the method taught by H. Zenno and T. Mizutani, (Chem. Abst.: 72:79122 (1970)) for the preparation of 7-nitro-1,2-benzothiazine-1,1-dioxide. The resulting benzothiazines can be isolated and subsequently alkylated by standard methods known to one skilled in the art. ##STR43##
Many of the nitro compounds of Formula XXIIIa where n is 0 can also be prepared from the corresponding 1,2-benzisothiazoles XXVI as shown in Equation 25. ##STR44##
Nitration of XXVIII gives, in part, the 7-nitro derivative which is isolated by standard methods. The derivative is converted to its 1,1-dioxide by treatment with hydrogen peroxide. Reduction of the carbon-nitrogen double bond with NaBH.sub.4 followed by alkylation of the resulting sulfonamide gives compounds XXIIIa where n is 0. The above reactions are characteristic of 1,2-benzisothiazoles XXVIII. For reviews of their synthesis and reactions, see L. L. Bambas, "The Chemistry of heterocyclic Compounds," Vol. 4, part III, 1952, p. 223-378, and M. Davis, Adv. Heterocyclic Chem., Vol. 14 (1972) p. 43-98. 1,2-Benzothiazines are also well known in the literature, for a review of their chemistry and alternate methods of their preparation see J. G. Lombardino, D. E. Kuhla, Adv. Heterocyclic Chem., Vol. 28 (1981) p. 73-126.
As shown in Equation 26, many of the nitro compounds of Formula XXIII where J=J.sub.6 (W.sub.1 =O) (XXIIId) can be prepared from the appropriately substituted amines XXV. R' is H or CH.sub.2 Cl. ##STR45##
The nitro amines XXV, previously described in Equation 23, can be converted into the corresponding cyano compounds XXIX by the "Sandmeyer Reaction" (T. Sandmeyer, Chem. Ber., 17, 1633, 2650 (1884)). The cyano function is hydrolyzed to a carboxylic acid by methods known to one skilled in the art, and the carboxylic acids or their corresponding esters can be (a) cyclized to the nitro isocoumarins XXIIId (n=1) by heating in the presence of base when R' is CH.sub.2 Cl, or (b) cyclized to the nitro phthalides XXIIId (n=0) when R' is H by first brominating with NBS or bromine (note discussion of Equation 12 for brominations when R.sub.1 ' is alkyl) followed by heating in a solvent such as aqueous dioxane. The latter method is that taught by J. A. Houbion et al., Org. Prep. and Procedures Int., 11, 27 (1979) for the preparation of 7-nitrophthalide (XXIIId, n=0, R.sub.1 '=R.sub.3 =H).
The procedure of Equation 26 is similar to the method of P. Banejce and D. Chaudhury, J. Org. Chem., 26, 4344 (1961) for the preparation of substituted isocoumarins; similar methods can be utilized for the preparation of isocoumarins of the J.sub.10 (W.sub.1 =O) type. Isocoumarins are well known in the literature, for a review of their synthesis and reactions see R. Barry, Chem. Rev., 64, 229-260 (1964).
Many of the nitro compounds of Formula XXIII, where n=0 can also be prepared by reduction of the corresponding 3-nitrophthalic anhydrides with either sodium borohydride or lithium aluminum hydride in tetrahydrofuran as taught by M. kayser and P. Morand, Can. J. Chem., 58, 2848 (1980) for the preparation of 7-nitrophthalide (XXIIId; n=0, R.sub.1 '=H). Phthalides and phthalic anhydrides are well known in the art, for a review of their synthesis and reactions see, S. Wawzonek, Heterocyclic Compounds, Vol. 2, John Wiley and Sons. Inc., New York, 1951.
As shown in Equation 27, many of the nitro compounds of Formula XXIII where J is J.sub.5 (W.sub.1 =O) (XXIIIe) can be prepared from the appropriately substituted benzonitriles XXIX. R' is H or CH.sub.2 Cl. ##STR46##
The benzonitriles XXIX, previously described in Equation 26, are hydrolyzed to carboxylic acids, converted to their corresponding acid chlorides by contacting with a reagent such as thionyl chloride and subsequently reacted with the appropriate amine, by standard methods, to give the amides XXX. The intermediate amides XXX can be cyclized to the nitro compounds XXIIIe by the procedures previously described in Equation 23 for converting sulfonamides of XXVI into nitro compounds XXIIIa.
Alternatively, many of the nitro compounds of Formula XXIIIe can be prepared from the nitro compounds of Formula XXIIId as shown in Equation 28. ##STR47##
The reactions of phthalides with amines to produce phthalimidines is well known, see C. Hollins, The Synthesis of Nitrogen Ring Compounds, Ernest Benn Limited, London, 1924. In these reactions, heating the phthalides (XXIIId, n=0) with an amine produces the phthalimidines (XXIIIe, n=0) directly, the intermediate alcohols XXXI (n=0) are not isolated. With the 3,4-dihydrocoumarins (XXIIId, n=1) the intermediate amide alcohols XXXI (n=1) are formed (see P. Maitte, Colloq. Intern. Centre Natl. Rech. Sci. (Paris), 64, 197 (1955), Chem. Abst., 55:10426 (1961)) and can be converted to the dihydroisoquinolines XXIIIe (n=1) by first conversion to the corresponding mesylate followed by heating with a base as described above in Equation 20 for the preparation of compounds XII (J=J.sub.1, R'=alkyl) and XV (J=J.sub.1, X=Cl) from the sulfonamide alcohols XX. For a comprehensive review of the synthesis and reactions of dihydroisoquinolones see N. J. McCorkindale, The Chemistry of Heterocyclic Compounds, Vol. 38, part III, John Wiley and Sons, New York, in press.
As shown in Equation 29, many of the nitro compounds of Formula XXIII where J is J.sub.7 (W.sub.1 =O) (XXIIIf) can be prepared from the appropriately substituted nitrobenzenes XXIV. R' is Br or CH.sub.2 Br. ##STR48##
The nitrobenzenes XXIV, previously discussed in Equation 23, are reacted with potassium cyanide in a solvent such as acetone to give nitrile intermediates which are hydrolized to the corresponding carboxylic acids XXXII by standard methods known to one skilled in the art. The nitro carboxylic acids XXXII, when reduced by standard methods (see discussion of Equation 22), spontaneously cyclize to give the lactams XXXIII. For a discussion of this reaction when n is 0, see W. Sumpter and F. Miller, The Chemistry of Heterocyclic Compounds, Vol. 32, John Wiley and Sons, New York, 1977, p. 216-217, and references cited therein. The nitro lactams XXIIIf are prepared in part from lactams XXXIII by standard nitration and alkylation procedures known to one skilled in the art.
Alternatively, many lactams XXXIII of Equation can be prepared from the substituted anilines XXXIV as shown in Equation 30. ##STR49##
The substituted anilines XXXIV are reacted with either a chloroacetyl chloride (n=0) or .beta.-chloropropionyl chloride (n=1, R.sub.3 =H) in the presence of an acid scavenger to give the chloro amides XXXV. The amides XXXV are cyclized by heating in the presence of a suitable Friedel-Crafts reagent such as AlCl.sub.3 to give the lactams XXXIII. The method of Equation 30 has been widely used for the preparation of oxindoles (XXXIII, n=0; see W. Sumpter and F. Miller, loc. cit., p. 135-136 for discussion and references) and for the preparation of 3,4-dihydro-2-quinolones (XXXIII, n=1; see G. Jones, loc. cit., p. 164-168 for discussion and references). For a general review of oxindole chemistry see W. Sumpter and F. Miller, loc. cit., p. 134-153.
Many of the nitro compounds of Formula XXIII in Equation 22 where J is J.sub.2, J.sub.3, J.sub.8 (W.sub.1 =O) and J.sub.9 (W.sub.1 =O) can be prepared from the corresponding nitro compounds of Formula XXIII where J is J.sub.1 (n=1), J.sub.4, J.sub.5 (W.sub.1 =O) and J.sub.7 (W.sub.1 =O), respectively, by the bromination-dehydrobromination sequence described above for sulfonamides IV in Equation 12.
The amines of Formula III in Equations 1 and 3 are also important intermediates for the preparation of the compounds of this invention and are described below.
The pyrimidines and triazines of Formula (IIIa) to (IIId) below are either known or can be prepared by methods obvious to one skilled in the art. ##STR50##
For a review of the synthesis and reactions of 2-aminopyrimidines (IIIa, Z=CR') see The Chemistry of Heterocyclic Compounds, Vol. 16, John Wiley and Sons, New York (1962). For a review of the synthesis and reactions of 2-amino-s-triazines (IIIa, Z=N) see The Chemistry of Heterocyclic Compounds, Vol. 13, John Wiley, New York (1959), F. C. Schaefer, U.S. Pat. No. 3,154,547 and F. C. Schaefer and K. R. Huffman, J. Org. Chem., 28, 1812 (1963). The synthesis of the bicyclic amines IIIb and IIIc is taught in European Patent Application No. 15,683. The synthesis of bicyclic amines IIId is taught in European Patent Application No. 46,677. The synthesis of amines IIIa where X is cyclopropyl is taught in South African Patent Application No. 83/7434.
The amines of Formula III where X is OCF.sub.2 H, OCH.sub.2 F, OCF.sub.3 or CF.sub.3 ; or X.sub.1 is OCF.sub.2 H and/or Y is OCH.sub.2 F, OCF.sub.3, SCH.sub.2 F, SCF.sub.3 or GCF.sub.2 T wherein G is O or S and T is H, CHClF, CHBrF or CHFCF.sub.3 can be prepared by methods that would be obvious to one skilled in the art.
The pyrimidines of Formula IIIa (Z=CH) where Y is ##STR51## can be prepared according to the methods known to one skilled in the art.
The triazine amines of Formula IIIe where X.sub.3 is CH.sub.3 or OCH.sub.3 and R is H or CH.sub.3 can be prepared according to the teachings of European Patent Application No. 94,260. ##STR52##
Preparation of 3-amino-1,2,4-triazoles of Formula IIIf are known in the art and 1,2,4-triazoles are reviewed in The Chemistry of Heterocyclic Compounds "Triazoles 1,2,4" (John Wiley and Sons, New York, 1981). Commonly used starting materials containing nitrogen are N-aminoguanidine, hydrazine, alkylhydrazines, cyanamide, ethyl cyanoacetimidate, dimethyl cyanodithioimidocarbonate, dimethyl cyanoimidocarbonate, ethoxymethylenecyanamide, and acylhydrazines. Some literature syntheses are illustrated below. Using these techniques or suitable modifications that would be apparent to one skilled in the art, the 3-amino-1,2,4-triazole intermediates can be readily prepared.
Heating equimolar amounts of ethyl propionimidate hydrochloride and N-aminoguanidine nitrate in pyridine gives 3-amino-5-ethyltriazole; German Patent No. 1,073,499 (1960); Berichte, 96, 1064 (1963). ##STR53## Condensation of hydrazine with ethyl N-cyanoacetimidate yields 3-amino-5-methyltriazole; Journal of Organic Chemistry, 28, 1816 (1963). ##STR54## U.S. Pat. No. 2,835,581 (1958) teaches the preparation of 3-amino-5-(hydroxymethyl)triazole from N-amino-guanidine and glycolic acid. ##STR55## Condensing hydrazine with dimethyl cyanodithioimidocarbonate in acetonitrile gives 3-amino-5-methylthio-1,2,4-triazole while reaction of hydrazine with dimethyl N-cyanoimidocarbonate produces 3-amino-5-methoxy-1,2,4-triazole; Journal of Organic Chemistry, 39, 1522 (1974). ##STR56##
Reaction of substituted hydrazines with N-cyanothioimidocarbonates (prepared according to the procedure given in D. M. Wieland, Ph.D. Thesis, 1971, pp. 123-124) yields disubstituted aminotriazoles as shown below. ##STR57##
Many of the aminoheterocyclic intermediates of Formula III where R is methyl may be prepared by a two-step procedure as described for IIIg in Equation 31, wherein X, Y and Z are as previously defined. ##STR58##
A solution of the amine XXXVI in concentrated hydrochloric acid is treated with sodium nitrate solution and the chloro compound XXXVII is isolated in the usual manner by filtration of the acidic solution. A representative procedure is described by Bee and Rose in J. Chem. Soc. C, 2031 (1966), for the case in which Z=CH, and X=Y=OCH.sub.3. Displacement of the chlorine of XXXVII may be accomplished by heating with an excess of methylamine in water to obtain the methylamino heterocycle (IIIg).
Quaternization of amino functionality present in the R.sub.2 group of compounds of formula I are also useful as herbicides and can be prepared by standard methods known to one skilled in the art.
Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride). 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.

EXAMPLE 1
2-t-Butyl-3-hydroxy-7-chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide
To a solution of 49.5 g of N-t-butyl-2-chlorobenzenesulfonamide in 875 mls of dry THF was added 262 ml of a 1.6M hexane solution of n-butyl lithium at -20.degree. to -5.degree. C. under an inert atmosphere. The mixture was stirred at 0.degree. C. for 1 hour, room temperature for 2 hours, recooled to -78.degree. C. and contacted with 38 mls of dry dimethylformamide. The mixture was allowed to warm to room temperature overight, poured into water, acidified to a ph of .about.3 and ether extracted. The extract was washed with water and brine, dried over MgSO.sub.4 and concentrated to give a yellow oil. The oil was dissolved in 50% ether in hexane solution and allowed to stand, giving, after filtration, 38 g of the title compound as colorless crystals, m.p. 139.degree.-141.degree. C.
90 MHz NMR (CDCl.sub.3) .delta.: 7.7-7.2 (m, 3H, arom); 5.9 (br. d, J=11 Hz, 1H, CH; 4.2 (br. d, J=11 Hz, 1H, OH; and 1.5 (s, 9H, CH.sub.3 's).
IR (nujol) 3440 cm.sup.-1.
EXAMPLE 2
7-Chloro-1,2-benzisothiazole-1,1-dioxide
A solution of 37 g of 2-t-butyl-3-hydroxy-7-chloro-2,3-dihydro-1,2-benzoisothiazole-1,1-dioxide and 0.2 g of tosic acid in 370 mls of benzene was refluxed through a Dean-Stark water separator for 16 hours, cooled in ice and filtered to give 18.9 g of the title compound as colorless crystals, m.p. 162.degree.-164.degree. C.
90 MHz NMR (CDCl.sub.3) .delta.: 9.15 (s, 1H, CH); and 8.0-7.7 (m, 3H, arom).
IR (nujol) 1445, 132, 1170 cm.sup.-1.
EXAMPLE 3
7-Chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide
A suspension of 17.9 g of 7-chloro-1,2-benzisothiazole-1,1-dioxide in 180 ml of absolute ethanol was cooled to 0.degree. C. and treated with 3.33 g of sodium borohydride at such a rate that the temperature remained below 5.degree. C. The mixture was warmed to room temperature for 30 minutes, recooled to 0.degree. C. and contacted with glacial acetic acid to destroy excess hydride. The mixture was concentrated to dryness, the resulting solid suspended in water, filtered, washed with water and dried in vacuo at 50.degree. C. for 16 hours to give 17.6 g of the title compound as a white powder, m.p. 159.degree.-161.degree. C.
90 MHz NMR (CDCl.sub.3 /DMSO-d.sub.6) .delta.: 7.9-7.2 (m, 3H, arom); 6.9 (br, 1H, NH); and 4.4 (s, 2H, CH.sub.2).
IR (nujol) 3220 cm.sup.-1.
EXAMPLE 4
2-Pentyl-7-chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide
A suspension of 10.2 g of 7-chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide, 8.3 g of potassium carbonate and 7.7 ml of 1-iodopentane was refluxed in 50 ml of ethanol for 28 hours, cooled, concentrated and added to 200 ml of water. The mixture was extracted with n-BuCl, the extract washed with water and brine, dried over MgSO.sub.4 and concentrated to give 13.3 g of an amber oil which was triturated with hexane to give 11.4 g of the title compound as a tan powder, m.p. 46.degree.-48.degree. C.
90 MHz NMR (CDCl.sub.3) .delta.: 7.7-7.2 (m, 3H, arom); 4.3 (s, 2H, CH.sub.2); 3.3 (t, 2H, CH.sub.3); and 2.0-0.7 (m, 9H, alkyl).
IR (nujol) 1573, 1300, 1170, 1158 cm.sup.-1.
EXAMPLE 5
2-Pentyl-7-(propylthio)-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide
To a solution of 5.0 g of potassium-t-butoxide in 40 ml of dry dimethylformamide was added 4.0 ml of propyl mercaptan at -5.degree. C. to 0.degree. C. under an inert atmosphere followed by 11.0 g of 2-pentyl-7-chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide. The mixture was stirred at room temperature for 16 hours, poured into water and extracted with n-butyl chloride. The extract was washed with water and brine, dried over MgSO.sub.4 and concentrated to give 10.3 g of the title compound as a yellow oil.
60 MHz NMR (CDCl.sub.3) .delta.: 7.7-7.0 (m, 3H, arom); 4.3 (s, 2H, CH.sub.2); 3.4-2.9 (m, 4H, CH.sub.2); and 2.0-0.8 (m, 14H, alkyl).
IR (neat) 1582, 1455, 1300, 1170, 1155 cm.sup.-1.
EXAMPLE 6
2-Pentyl-2,3-dihydro-1,2-benzisothiazole-7-sulfonamide-1,1-dioxide
A solution of 9.5 g of 2-pentyl-7-(propylthio-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide in 40 ml of acetic acid containing 1.3 ml of water was contacted with 7.0 ml of liquified chlorine at 10.degree. to 15.degree. C. and allowed to warm to 25.degree. C. The excess chlorine was removed via a stream of nitrogen gas and the solution was poured onto ice. The resulting solid was filtered, washed with water and hexane, dried, dissolved in CH.sub.2 Cl.sub.2 and contacted with 2.0 ml of liquified ammonia at -78.degree. to 25.degree. C. The mixture was added to 100 ml of 1N HCl and extracted with CH.sub.2 Cl.sub.2. The extract was washed with water and brine, dried over MgSO.sub.4, concentrated and slurried in ether to give 6.35 g of the title compound as a white powder, m.p. 156.degree.-160.degree. C.
60 MHz NMR (CDCl.sub.3 /DMSO-d.sub.6) .delta.: 8.2-7.6 (m, 3H, arom); 6.7 (b, 2H, NH.sub.2); 4.4 (s, 2H, CH.sub.2); 3.3 (t, 2H, CH.sub.2); and 2.0-0.8 (m, 9H, alkyl).
IR (nujol) 3370, 3270, 1540, 1285 cm.sup.-1.
EXAMPLE 7
N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pentyl-2,3-dihydro-1,2-benzisothiazole-7-sulfonamide-1,1-dioxide
A solution of 0.32 g of 2-pentyl-2,3-dihydro-1,2-benzisothiazole-7-sulfonamide-1,1-dioxide and 0.28 g of O-phenyl-N-(4,6-dimethoxypyrimidin-2-yl)carbamate in 5 ml of dry acetonitrile was treated with 0.15 ml of 1,8-diazobicyclo[5.4.0]undec-7-ene. The solution was stirred at 25.degree. C. for 10 minutes, diluted with 10 ml of water, cooled to 0.degree. C. and acidified with 1N HCl. The resulting precipitate was filtered, washed with water and ether and air dried to give 0.43 g of the title compound as a white powder, m.p. 197.degree.-203.degree. C.
200 MHz NMR (CDCl.sub.3) .delta.: 13.0 (b, 1H, NH); 8.34 (d, 1H, arom); 7.77 (t, 1H, arom); 7.64 (d, 1H, arom); 7.12 (b, 1H, NH); 5.77 (s, 1H, CH); 4.34 (s, 2H, CH.sub.2); 4.00 (s, 6H, OCH.sub.3 's); 3.24 (m, 2H, CH.sub.2); 1.75 (m, 2H, CH.sub.2); 1.36 (m, 4H, CH.sub.2 's); and 0.88 (t, 3H, CH.sub.3).
IR (nujol) 1730, 1710, 1610 cm.sup.-1.
EXAMPLE 8
N-Methylisoindolin-1-thione-7-sulfonamide
A mixture of 0.68 g of N-methylisoindolin-1-one-7-sulfonamide, 0.61 g of Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) and 15 ml of xylene was heated to reflux under nitrogen for 24 hours. The mixture was allowed to cool, the solid products collected, and recrystallized from isopropanol (carbon) to give 0.31 g of the title compound as a yellow solid, m.p. 231.degree.-232.degree. C.
90 MHz NMR (CDCl.sub.3 /DMSO-d.sub.6) .delta.: 3.60 (s, 3H, NCH.sub.3); 5.08 (s, 2H, CH.sub.2); 7.28 (s, 2H, NH.sub.2); and 7.5-8.3 (m, 3H, arom).
EXAMPLE 9
N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methylisoindolin-1-thione-7-sulfonamide
To a mixture of 0.14 g of N-methylisoindolin-1-thione-7-sulfonamide and 0.16 g of N-(4,6-dimethoxypyrimidin-2-yl)-O-phenylcarbamate in 5 ml of acetonitrile was added dropwise 0.085 ml of DBU. The deep red solution was stirred for 30 minutes, diluted with 5 ml of water, acidified to pH 6 with 5% HCl, the solid collected, washed with water, washed with ether, and dried in vacuo to give 0.06 g of the title compound as a pale yellow solid, m.p. 202.degree.-203.5.degree. C. (d).
200 MHz NMR (CDCl.sub.3): .delta. 3.61 (s, 3H, NCH.sub.3); 3.96 (s, 6H, OCH.sub.3 's); 5.28 (s, 2H, CH.sub.2); 5.80 (s, 1H, pyrimidine C.sub.5 -H); 7.15 (broad s, 1H, NH); 7.6 (t, 1H); 8.1 (d, 1H); 8.3 (d, 1H); and 12.9 (broad s, 1H, NH).
IR (nujol) 1720 cm.sup.-1.
Using the procedures of Examples 1 to 9 and the methods described herein, the following compounds of Tables I-V can be prepared.
TABLE Ia ##STR59## W n R R.sub.1 R.sub.2 R.sub.3 X Y Z m.p. (.degree.C.) O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 189-193 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 190-197 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 197-203 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 172-175 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 154-158 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 204-206 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 204-206 O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 202-205 O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 227-229 O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 176-177 O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 175-178 O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 215-218 O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Ph H CH.sub.3 CH.sub.3 CH 194-195 O 0 H H CH.sub.2 Ph H CH.sub.3 OCH.sub.3 CH 183-186 O 0 H H CH.sub.2 Ph H OCH.sub.3 OCH.sub.3 CH 216-218 O 0 H H CH.sub.2 Ph H CH.sub.3 OCH.sub.3 N 180-184 O 0 H H CH.sub.2 Ph H OCH.sub.3 OCH.sub.3 N 179-183 O 0 H H CH.sub.2 Ph H Cl OCH.sub.3 CH 205-210 O 0 H H CH.sub.2 Ph H Br OCH.sub.3 CH O 0 H H OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H OCH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H OCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H OCH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H OCH(CH.sub .3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH 220-221 O 0 H H CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH 223-224 O 0 H H CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH 210-214 O 0 H H CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 N 175-177 O 0 H H CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 N 193-195 O 0 H H CH.sub.2 CHCH.sub.2 H Cl OCH.sub.3 CH 213-215 O 0 H H CH.sub.2 CHCH.sub.2 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CHCHCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CHCHCH.sub.3 H CH.sub.3 OCH.sub.3 CH 215-217 O 0 H H CH.sub.2 CHCHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 219-222 O 0 H H CH.sub.2 CHCHCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHCHCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHCHCH.sub.3 H Cl OCH.sub.3 CH 216-218 O 0 H H CH.sub.2 CHCHCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C C(CH.sub.3)H.sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H Br OCH.sub.3 CH O 0 H H CH(CH.sub.3)CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH(CH.sub.3)CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.3 CH.sub.3 CH 202-204(d) O 0 H H CH.sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH 198-200(d) O 0 H H CH.sub.2 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH 201.5-204(d) O 0 H H CH.sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CHCH.sub.2 H Cl OCH.sub.3 CH 208-210(d) O 0 H H CH.sub.2 CH.sub.2 CHCH.sub.2 H Br OCH.sub.3 CH O 0 H H CH.sub.2 C(Cl)CH.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 C(Cl)CH.sub.2 H CH.sub.3 OCH.sub.3 CH 216-217 O 0 H H CH.sub.2 C(Cl)CH.sub.2 H OCH.sub.3 OCH.sub.3 CH 215-216 O 0 H H CH.sub.2 C(Cl)CH.sub.2 H Cl OCH.sub.3 CH 217-218 O 0 H H CH.sub.2 C(Cl)CH.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(Cl)CH.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHCHCH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHCHCH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(F)CHF H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(F)CHF H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH 211- 213 O 0 H H CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH 194-196 O 0 H H CH.sub.2 CCCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH(CH.sub.3)CCH H CH.sub.3 OCH.sub.3 CH O 0 H H CH(CH.sub.3)CCH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCCH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCCH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCCH.sub.2 OH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCCH.sub.2 OH H OCH.sub.3 OCH.sub.3 CH O 0 H H CF.sub.2 H H CH.sub.3 CH.sub.3 CH O 0 H H CF.sub.2 H H CH.sub.3 OCH.sub.3 CH O 0 H H CF.sub.2 H H OCH.sub.3 OCH.sub.3 CH O 0 H H CF.sub.2 H H CH.sub.3 OCH.sub.3 N O 0 H H CF.sub.2 H H OCH.sub.3 OCH.sub.3 N O 0 H H CF.sub.2 H H Cl OCH.sub.3 CH O 0 H H CF.sub.2 H H Br OCH.sub.3 CH O 0 H H CF.sub.2 CF.sub.2 H H CH.sub.3 CH.sub.3 CH O 0 H H CF.sub.2 CF.sub.2 H H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CF.sub.3 H CH.sub.3 CH.sub.3 CH 215-216 O 0 H H CH.sub.2 CF.sub.3 H CH.sub.3 OCH.sub.3 CH 218-219 O 0 H H CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH 198-199 O 0 H H CH.sub.2 CF.sub.3 H CH.sub.3 OCH.sub.3 N 168-170 O 0 H H CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 N 158-163 O 0 H H CH.sub.2 CF.sub.3 H Cl OCH.sub.3 CH 211-213 O 0 H H CH.sub.2 CF.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CH 214-215 O 0 H H CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 CH 218-219 O 0 H H CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH 212-214 O 0 H H CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 N 190-192 O 0 H H CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 N 195-196 O 0 H H CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH 215-217 O 0 H H CH.sub.2 CH.sub.2 F H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 Cl H CH.sub.3 CH.sub.3 CH 204-205 O 0 H H CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH 216-217 O 0 H H CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH 206-208 O 0 H H CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 N 127-128 O 0 H H CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 N 132-133 O 0 H H CH.sub.2 CH.sub.2 Cl H Cl OCH.sub.3 CH 219-220 O 0 H H CH.sub.2 CH.sub.2 Cl H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 Br H CH.sub.3 CH.sub.3 CH 215-216 O 0 H H CH.sub.2 CH.sub.2 Br H CH.sub.3 OCH.sub.3 CH 211-212 O 0 H H CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.3 CH 210-212 O 0 H H CH.sub.2 CH.sub.2 Br H CH.sub.3 OCH.sub.3 N 168-171 O 0 H H CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.3 N 121-123 O 0 H H CH.sub.2 CH.sub.2 Br H Cl OCH.sub.3 CH 222-224 O 0 H H CH.sub.2 CH.sub.2 Br H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(Cl)CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(Cl)CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(Br)CH.sub.2 Br H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(Br)CH.sub.2 Br H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCl.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCl.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(OH)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(OH)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH 228-230 O 0 H H CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH 234-236 O 0 H H CH.sub.2 CH.sub.2 CN H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH 228-230 O 0 H H CH.sub.2 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH 198-193 O 0 H H CH.sub.2 CH.sub.2 CN H CH.sub.3 OCH.sub.3 N 173-176 O 0 H H CH.sub.2 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 N 199-203 O 0 H H CH.sub.2 CH.sub.2 CN H Cl OCH.sub.3 CH 231-235 O 0 H H CH.sub.2 CH.sub.2 CN H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CN H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CN H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH 185-187 O 0 H H CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 184-186 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH 171-175 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 194-197 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 195-198 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 193-194 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 203-204 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 193-195 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 187-189 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 193-197 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(OCH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.3).sub.2 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SCH.sub.3 H CH.sub.3 CH.sub.3 CH 189-190 O 0 H H CH.sub.2 CH.sub.2 SCH.sub.3 H CH.sub.3 OCH.sub.3 CH 192-193 O 0 H H CH.sub.2 CH.sub.2 SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 20-201 O 0 H H CH.sub.2 CH.sub.2 SCH.sub.3 H CH.sub.3 OCH.sub.3 N 163-164 O 0 H H CH.sub.2 CH.sub.2 SCH.sub.3 H OCH.sub.3 OCH.sub.3 N 168-169 O 0 H H CH.sub.2 CH.sub.2 SCH.sub.3 H Cl OCH.sub.3 CH 210-211 O 0 H H CH.sub.2 CH.sub.2 SCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 175-180 O 0 H H CH.sub.2 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 178-184 O 0 H H CH.sub.2 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 188-192 O 0 H H CH.sub. 2 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 161-164 O 0 H H CH.sub.2 CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 128-130 O 0 H H CH.sub.2 CO.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 179-180 O 0 H H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 173-176 O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 214-218 O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 215-217 O 0 H H CH.sub.2 CH(CH.sub.3)CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 N(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Si(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH 195-197 O 0 H H CH.sub.2 Si(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH 196-198 O 0 H H C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH 223-224 O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 191-193 O 0 H H C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 205-206 O 0 H H C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 160-161 O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 205-206 O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 198-199 O 0 H H SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H cyclopropyl H CH.sub.3 OCH.sub.3 CH O 0 H H cyclopropyl H OCH.sub.3 OCH.sub.3 CH O 0 H H cyclopropyl H CH.sub.3 OCH.sub.3 N O 0 H H cyclopentyl H CH.sub.3 OCH.sub.3 CH 168-170 O 0 H H cyclopentyl H OCH.sub.3 OCH.sub.3 CH 186-189 O 0 H H cyclopentyl H CH.sub.3 OCH.sub.3 N 182-183 O 0 H H cyclopentyl H Cl OCH.sub.3 CH 233-235 O 0 H H cyclohexyl H CH.sub.3 OCH.sub. 3 CH 222-224 O 0 H H cyclohexyl H OCH.sub.3 OCH.sub.3 CH 224-227 O 0 H H CH.sub.2 -cyclopropyl H CH.sub.3 CH.sub.3 CH 222.degree.d O 0 H H CH.sub.2 -cyclopropyl H CH.sub.3 OCH.sub.3 CH 166-169 O 0 H H CH.sub.2 -cyclopropyl H OCH.sub.3 OCH.sub.3 CH 221-223 O 0 H H CH.sub.2 -cyclopropyl H CH.sub.3 OCH.sub.3 N 193-196 O 0 H H CH.sub.2 -cyclopropyl H OCH.sub.3 OCH.sub.3 N 204-206 O 0 H H CH.sub.2 -cyclopropyl H Cl OCH.sub.3 CH 215-217 O 0 H H CH.sub.2 -cyclopropyl H Br OCH.sub.3 CH O 0 H H CH.sub.2 -cyclopentyl H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 -cyclopentyl H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 -cyclopentyl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 -cyclopentyl H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 -cyclopentyl H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 -cyclopentyl H Cl OCH.sub.3 CH O 0 H H CH.sub. 2 -cyclopentyl H Br OCH.sub.3 CH O 0 H H CH.sub.2 -cyclohexyl H CH.sub.3 CH.sub.3 CH 195-198 O 0 H H CH.sub.2 -cyclohexyl H CH.sub.3 OCH.sub.3 CH 148-150 O 0 H H CH.sub.2 -cyclohexyl H CH.sub.3 OCH.sub.3 CH 201-204 O 0 H H CH.sub.2 -cyclohexyl H CH.sub.3 OCH.sub.3 CH 188-191 O 0 H H CH.sub.2 -cyclohexyl H CH.sub.3 OCH.sub.3 CH 168-170 O 0 H H CH.sub.2 -cyclohexyl H CH.sub.3 OCH.sub.3 CH 175-178 O 0 H H CH.sub.2 -cyclohexyl H CH.sub.3 OCH.sub.3 CH 161-164 O 0 H H CH.sub.2O H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2O H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHCl.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHCl.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 CH.sub.3 CH 194-197 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub. 3 CH 176-183 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH 201-203 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 N 181-183 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 N 176-178 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H Cl OCH.sub.3 CH 186-188 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Br H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Br H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Br H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Br H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Br H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH(Cl)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(Cl)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Cl H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Cl H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 Cl H Cl OCH.sub.3 CH O 0 H H CH.sub.2 Cl H Br OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3OCH.sub.3 CH O 0 H .sub.-- m-F CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub. 3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH OCH CH 163-171 O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 171-176 O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCF.sub.2 H CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.2 CH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CF.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCF.sub.2 H CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 N O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.3 H Br OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H m .sub.---CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH(CH.sub.3 ).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.s ub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 N O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H Br OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 N O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H m .sub.---OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 1 H H CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub. 3 H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 SCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 Ch.sub.2 OCH.sub.3 H OCH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H F OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCF.sub.2 H OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.2 F OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H CF.sub.3 CF.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub. 3 H OCH.sub.3 H CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.2 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH.sub.2 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 NH.sub.2 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 NHCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 N(CH.sub.3).sub.2 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 N(OCH.sub.3)CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH.sub.2 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 SCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.2 CHCH.sub.2 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.2 CCH CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CN CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 N.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH.sub.2 SCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCF.sub.2 H CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 SCF.sub.2 H CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCF.sub.2 CHClF CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCF.sub.2 CHBrF CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCF.sub.2 CHFCF.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CHO CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 C(O)CH.sub.3 CH O 0 H H CH.sub. 2 CH.sub.2 OCH.sub.3 H OCH.sub.3 C(O)CH.sub.2 CH.sub.3 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 C(O)CH.sub.2 CH.sub.2 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH(OCH.sub.3).sub.2 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH(SCH.sub.3).sub.2 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH(OCH.sub.2 CH.sub.3).sub.2 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH(SCH.sub.2 CH.sub.2 CH.sub.3).sub.2 CH OCH.sub.3 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CCH.sub.3 CH SCH.sub.3 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 1,3-dioxolan- CH 2-yl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 1,3-dioxolan- CH 2-yl O 0 H H CH.sub. 2 CH.sub.2 OCH.sub.3 H OCH.sub.3 1,3-dithiolan- CH 2-yl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 C(OCH.sub.3).sub.2 CH CH.sub.2 CH.sub.2 CH.sub.3 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CCH.sub.3 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CCH.sub.2 CH.sub.3 O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CCl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CBr O 0 H H (CH.sub.2).sub.5 CH.sub.3 H CH.sub.3 CH.sub.3 CH 195-196 O 0 H H (CH.sub.2).sub.5 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 196-197 O 0 H H (CH.sub.2).sub.5 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 205-207 O 0 H H (CH.sub.2).sub.5 CH.sub.3 H CH.sub.3 OCH.sub.3 N 149-151 O 0 H H (CH.sub.2).sub.5 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 164-166 O 0 H H (CH.sub.2).sub.5 CH.sub.3 H Cl OCH.sub.3 CH 215-218 O 0 H H (CH.sub.2).sub.5 CH.sub.3 H Br OCH.sub.3 CH O 0 H H (CH.sub.2).sub.3 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H (CH.sub.2).sub.3 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 172-176 O 0 H H CH.sub.2 CH.sub.2 O(CH.sub.2).sub.9 CH.sub.3 OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCF.sub.2 H H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 O(CH.sub.2).sub.9 CF.sub.3 H OCH.sub. 3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 S(CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SCF.sub.2 H H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 S(CH.sub.2).sub.9 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO(CH.sub.2).sub.7 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SOCH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub. 2 CH.sub.2 OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 COCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 COCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 COCH.sub. 3 H OCH.sub.3 OCH.sub.3 CH 178-182 O 0 H H CH.sub.2 COCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 COCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 COCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 COCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 COCH.sub.3 H CH.sub.3 CH.sub.3 CH 200-201 O 0 H H CH.sub.2 CH.sub.2 COCH.sub.3 H CH.sub.3 OCH.sub.3 CH 175-180 O 0 H H CH.sub.2 CH.sub.2 COCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 182-190 O 0 H H CH.sub.2 CH.sub.2 COCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 COCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 COCH.sub.3 H Cl OCH.sub.3 CH 201-205 O 0 H H CH.sub.2 CH.sub.2 COCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 COCH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO(CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 COCH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO(CH.sub.2).sub.5 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO(CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OCOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCOCH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO(CH.sub.2).sub.9 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 (CH.sub.2).sub.5 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 (CH.sub.2).sub.5 CH.sub.2 Br OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHO H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NH(CH.sub.2).sub.5 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3)CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHCOCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHCOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OH H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OH H Br OCH.sub.3 CH O 0 H H CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H ##STR60## H OCH.sub.3 OCH.sub.3 CH O 0 H H ##STR61## H OCH.sub.3 OCH.sub.3 CH O 0 H H ##STR62## H OCH.sub.3 OCH.sub.3 CH O 0 H H ##STR63## H OCH.sub.3 OCH.sub.3 CH O 0 H H ##STR64## H OCH.sub.3 OCH.sub.3 CH O 0 H H ##STR65## H OCH.sub.3 OCH.sub.3 CH O 0 H H ##STR66## H CH.sub.3 CH.sub.3 CH 214-216 O 0 H H ##STR67## H CH.sub.3 OCH.sub.3 CH 204-207 O 0 H H ##STR68## H OCH.sub.3 OCH.sub.3 CH 208-210 O 0 H H ##STR69## H Cl OCH.sub.3 CH 228-230 O 0 H H ##STR70## H Br OCH.sub. 3 CH O 0 H H ##STR71## H CH.sub.3 OCH.sub.3 N 201-203 O 0 H H ##STR72## H OCH.sub.3 OCH.sub.3 N 194-197 O 0 H H ##STR73## H OCH.sub.3 OCH.sub.3 CH 201-204 O 0 H H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H CH.sub.3 CH.sub.3 CH 206-207 O 0 H H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH 188-190 O 0 H H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 208-210 O 0 H H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 N 195-196 O 0 H H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 N 195-196 O 0 H H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H Cl OCH.sub.3 CH 209-211 O 0 H H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CHCH(CH.sub.2).sub.6 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C C(CH.sub.2).sub.6 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H O(CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CO(CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CO.sub.2 (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CCC.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H COCH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H H COCH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H COC.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 214-219 O 0 H H CHCHCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- CH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- CH.sub.2 CH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCH.sub.2 CH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- CH.sub.2 OCH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCF.sub.2 H N propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- SCF.sub.2 H N propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCH.sub.2 CF.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- CF.sub.3 N propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCH.sub.2 CHCH.sub.2 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCH.sub.2 CCH N propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- NHCH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- N(CH.sub.3).sub.2 N propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- CH(OCH.sub.3).sub.2 CH propyl O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H cyclo- OCH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H cyclo- OCH.sub.3 N propyl O 0 H H CH.sub.2 CHCH.sub.2 H cyclo- OCH.sub.3 CH propyl O 0 H H CH.sub.2 CHCH.sub.2 H cyclo- OCH.sub.3 N propyl O 0 H H CH.sub.2 C CHHCH.sub.3 H cyclo- OCH.sub.3 CH propyl O 0 H H CH.sub.2 CHCHCH.sub.3 H cyclo- OCH.sub.3 N propyl O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H cyclo- OCH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H cyclo- OCH.sub.3 N propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCH.sub.3 CH propyl O 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H cyclo- OCH.sub.3 N propyl O 0 H H CH.sub.2 CHCH.sub.2 H cyclo- OCH.sub.3 CH propyl O 0 H H CH.sub.2 CHCH.sub.2 H cyclo- OCH.sub.3 N propyl O 0 H H CH.sub.2 Si(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH 190-193 O 0 H H CH.sub.2 Si(CH.sub.3).sub.3 H Cl OCH.sub.3 CH 201-202 O 0 H H CH.sub.2 Si(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N 190-193 O 0 H H CH.sub.2 Si(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N 138-141 O 0 H H (CH.sub.2).sub .9 CH.sub.3 H CH.sub.3 CH.sub.3 CH 167-169 O 0 H H (CH.sub.2).sub.9 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 159-163 O 0 H H (CH.sub.2).sub.9 CH.sub.3 H Cl OCH.sub.3 N 123-125 O 0 H H (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub. 3 N 141-145 O 0 H H CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 218-220 O 0 H H CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.2 CH 241-244 O 0 H H CO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 171-173 O 0 H H CO.sub.2 Et H OCH.sub.3 CH.sub.3 CH 210-215 O 0 H H CO.sub.2 Et H CH.sub.3 CH.sub.3 CH 185-187 O 0 H H CO.sub.2 Pr H OCH.sub.3 OCH.sub.3 CH 143-150 O 0 H H CO.sub.2 Pr H OCH.sub.3 CH.sub.3 CH 190-195 O 0 H H CO.sub.2 Pr H CH.sub.3 CH.sub.3 CH 214-216 O 0 H H CO.sub.2 Bu H OCH.sub.3 OCH.sub.3 CH 148-150 O 0 H H CO.sub.2 Bu H OCH.sub.3 CH.sub.3 CH 162-165 O 0 H H CO.sub.2 Bu H CH.sub.3 CH.sub.3 CH 198-202 O 0 H H CO.sub.2 iBu H OCH.sub.3 OCH.sub.3 CH 182-186 O 0 H H CO.sub.2 iBu H OCH.sub.3 CH.sub.3 CH 171- 174 O 0 H H CO.sub.2 iBu H CH.sub.3 CH.sub.3 CH 198-200 O 0 H H CO.sub.2 Pentyl H OCH.sub.3 OCH.sub.3 147-149 O 0 H H CO.sub.2 Pentyl H OCH.sub.3 CH.sub.3 CH 140-148 O 0 H H CO.sub.2 Pentyl H CH.sub.3 CH.sub.3 CH 175-176 O 0 H H CO.sub.2 Hexyl H OCH.sub.3 OCH.sub.3 CH 130-135 O 0 H H CO.sub.2 Hexyl H OCH.sub.3 OCH.sub.3 CH 155-156 O 0 H H CO.sub.2 Hexyl H OCH.sub.3 OCH.sub.3 CH 166-168 O 0 H H CO.sub.2 CH.sub.2 Ph H OCH.sub.3 OCH.sub.3 CH 188-190 O 0 H H CO.sub.2 CH.sub.2 Ph H OCH.sub.3 OCH.sub.3 CH 194-197 O 0 H H CO.sub.2 CH.sub.2 Ph H OCH.sub.3 OCH.sub.3 CH 173-179 O 0 H H CO.sub.2 -.sub.-i-Pr H OCH.sub.3 OCH.sub.3 CH 210-215 O 0 H H CO.sub.2 -.sub.-i-Pr H CH.sub.3 OCH.sub.3 CH 219-224 O 0 H H CO.sub.2 -.sub.-i-Pr H Cl OCH.sub.3 CH 194-199 O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H Cl OCH.sub.3 CH O 0 H H CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 239-241 O 0 H H CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 238-241 O 0 H H CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 217-219 O 0 H H CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 219-220 O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 219-223 O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 197-199 O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 183-189 O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 209-211 O 0 H H CH(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 219-225 O 0 H H CH(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 223-225 O 0 H H CH(CH.sub.2 CH.sub.3).sub.2 H Cl OCH.sub.3 CH 220-223 O 0 H H CH(CH.sub.2 CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 149-152 O 0 H H CH(CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 139-143 O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub. 3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CHOCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CHOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 I H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 I H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 I H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 I H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 I H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 I H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CH 210-211 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 CH 216-217 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH 199-200 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH 222-224 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 N 148-149 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 N 182-184 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub. 2 CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CF.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CF.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CF.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CF.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CF.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CF.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH 190-192 O 0 H H CH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH 172-174 O 0 H H CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N 171-173 O 0 H H CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N 116-119 O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub. 2 CH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub. 2 C(OCH.sub.3).sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 C(OCH.sub.3).sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2CH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2CH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2CH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2CH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2CH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2CH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H (2-cyclopentoxy)ethyl H CH.sub.3 OCH.sub.3 CH O 0 H H (2-cyclopentoxy)ethyl H OCH.sub.3 OCH.sub. 3 CH O 0 H H phenoxymethyl H CH.sub.3 OCH.sub.3 CH O 0 H H phenoxymethyl H OCH.sub.3 CH.sub.3 CH O 0 H H 2-phenoxyethyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-phenoxyethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (4-chlorophenoxy)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (4-chlorophenoxy )methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (4-chlorophenoxy)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (4-chlorophenoxy)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CCH.sub.2 (CH.sub.2).sub.6 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CCH.sub.2 (CH.sub.2).sub.6 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)CCCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)(cyclopropyl) H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)C.sub. 6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)NHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)NHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)NHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)NH(CH.sub.2).sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OC(O)NHC.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 CF.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OP(O)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OP(O)(OCH.sub.2 CH.sub.2 CH.sub. 2 CH.sub.2) H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 P(O)(OCH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 P(O)(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 P(O)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 P(O)(OCH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 P(O)(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 P(O)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OP(S)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OP(S)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.2 (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.2 CH.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OCi(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SOCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SOCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SC.sub.6 H.sub.5 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 SC.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SC.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SC.sub.6 H.sub.5 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 SC.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 SC.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 SCN H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SCN H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SCN H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SCN H OCH.sub.3 OCH.sub.3 CH 193-195 O 0 H H CH.sub.2 CN H CH.sub.3 CH.sub.3 CH 230-234 O 0 H H CH.sub.2 CN H Cl OCH.sub.3 CH 238-241 O 0 H H CH.sub.2 CN H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CN H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SP(O)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SP(S)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 P(S).sub.2 (OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 NH.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 NH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 NH CH.sub. 2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 N.sup..sym. (CH.sub.3).sub.3 Cl.sup..crclbar. H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N.sup..sym. (CH.sub.3).sub.3 I.sup..sym. H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHCO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHC(O)NH CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHC(O)NH CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NHP(O)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHP(S)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 NO.sub.2 H Cl CH.sub.3 CH O 0 H H CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NO.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NO.sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(O)C.sub.6 H.sub.5 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 C(O)C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(O)C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 193-199 O 0 H H CH.sub.2 C(O)C.sub.6 H.sub.5 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 C(O)C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(O)C.sub.6 H.sub. 5 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 C(O)C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 C(O)C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 164-166 O 0 H H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CO.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH 168-172 O 0 H H CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH 178-180 O 0 H H CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3 H Cl OCH.sub.3 CH 156-159 O 0 H H CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub.2 H H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 H H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 H H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 H H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 H H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub.2 H H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)CN H CH.sub.3 CH.sub.3 CN O 0 H H CH.sub.2 CH(CH.sub.3)CN H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)CN H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)CN H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(O)NHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(O)NHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(O)N(CH.sub.3 ).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H (1-naphthyl)methyl H CH.sub.3 OCH.sub.3 CH 163-169 O 0 H H (1-naphthyl)methyl H OCH.sub.3 OCH.sub.3 CH 220-228 O 0 H H (2-naphthyl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (2-naphthyl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (2-methylpyri dinium)- H CH.sub.3 OCH.sub.3 CH methyl iodide O 0 H H (2-methylpyrid inium)- H OCH.sub.3 OCH.sub.3 CH methyl iodide O 0 H H pyridin-2-ylme thyl H CH.sub.3 CH.sub.3 CH O 0 H H pyridin-2-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H pyridin-2-ylmethyl H OCH.sub.3 OCH.sub.3 CH 172-174 O 0 H H pyridin-2-ylmethyl H Cl OCH.sub.3 CH O 0 H H pyridin-2-ylmethyl H CH.sub.3 OCH.sub.3 N O 0 H H pyridin-2-ylmethyl H OCH.sub.3 OCH.sub.3 N O 0 H H pyridin-3-ylmethyl H CH.sub.3 CH.sub.3 CH O 0 H H pyridin-3-ylm ethyl H CH.sub.3 OCH.sub.3 CH O 0 H H pyridin-3-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H pyridin-3-ylmethyl H Cl OCH.sub.3 CH O 0 H H pyridin-3-ylmethyl H CH.sub.3 OCH.sub.3 N O 0 H H pyridin-3-ylmethyl H OCH.sub.3 OCH.sub.3 N O 0 H H pyridin-4-ylmethyl H CH.sub.3 CH.sub.3 CH O 0 H H pyridin-4-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H pyridin-4-ylme thyl H OCH.sub.3 OCH.sub.3 CH O 0 H H pyridin-4-ylmethyl H Cl OCH.sub.3 CH O 0 H H pyridin-4-ylmethyl H CH.sub.3 OCH.sub.3 N O 0 H H pyridin-4-yl methyl H OCH.sub.3 OCH.sub.3 N O 0 H H thien-2-ylmethyl H CH.sub.3 CH.sub.3 CH O 0 H H thien-2-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H thien-2-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H thien-2-ylmethyl H Cl OCH.sub.3 CH O 0 H H thien-2-ylmethyl H CH.sub.3 OCH.sub.3 N O 0 H H thien-2-ylmethyl H OCH.sub.3 OCH.sub.3 N O 0 H H thien-3-ylmethyl H CH.sub.3 CH.sub.3 CH
W n R R.sub.1 R.sub.2 R.sub.3 X Y Z m.p. (.degree.C.) O 0 H H thien-3-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H thien-3-ylmet hyl H OCH.sub.3 OCH.sub.3 CH O 0 H H thien-3-ylmethyl H H Cl OCH.sub.3 CH O 0 H H thien-3-ylmethyl H CH.sub.3 OCH.sub.3 N O 0 H H thien-3-ylmeth yl H OCH.sub.3 OCH.sub.3 N O 0 H H (5-methylthien-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (5-methylthien-2-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (5-chlorothien-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (5-chlorothien-2-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (5-cyanothien -2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (5-cyanothien-2-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H furan-2-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H furan-2-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (5-methylfuran- 2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (5-methylfuran-2-yl)methyl H OCH.sub. 3 OCH.sub.3 CH O 0 H H furan-3-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H furan-3-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (4.5-dihydrofur an-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (4.5-dihydrofuran-2-yl)met hyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (1H-pyrrol-1-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (1H-pyrrol-1-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (1H-pyrrol-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (1H-pyrrol-2-y l)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (1-methyl-1H-pyrrol-3-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (1-methyl-1H-pyrrol-3-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H oxazol-2-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H oxazol-2-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H thiazol-2-ylme thyl H CH.sub.3 OCH.sub.3 CH O 0 H H thiazol-2-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (4.5-dihydro-4.4-dimethyl- H CH.sub.3 OCH.sub.3 CH oxazol-2-yl)methyl O 0 H H (4.5-dihydro-4.4-dimethyl- H OCH.sub.3 OCH.sub.3 CH oxazol-2-yl)methyl O 0 H H isoxazol-3-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H isoxazol-3-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (1,2,4-oxadiazol-3-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (1,2,4-oxadiazol-3-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (5-methyl-1 ,2,4-oxadiazol- H CH.sub.3 OCH.sub.3 CH 3-yl)methyl O 0 H H (5-methyl -1,2,4-oxadiazol- H OCH.sub.3 OCH.sub.3 CH 3-yl)methyl O 0 H H (5-methyl-1,3,4-oxadiazol- H CH.sub.3 OCH.sub.3 CH 2-yl)methyl O 0 H H (5-methyl-1,3,4-oxadiazol- H OCH.sub.3 OCH.sub.3 CH 2-yl)methyl O 0 H H 1H-pyrazol-1-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H 1H-pyrazol-1- ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 4H-pyrazol-1-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H 1H-1,2,4,triazol-1-ylmethyl H CH.sub.3 OCH.sub.3 CH O 0 H H 1H-1,2,4,triazol-1-ylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (1-methyl-1H-imidazol- H CH.sub.3 OCH.sub.3 CH 2-yl)methyl O 0 H H (1-methyl-1H-imidazol- H OCH.sub.3 OCH.sub.3 CH 2-yl)methyl O 0 H H (1-methyl-1H-1,2,4- H CH.sub.3 OCH.sub.3 CH triazol-5-yl)meth yl O 0 H H (1-methyl-1H-1,2,4- H OCH.sub.3 OCH.sub.3 CH triazol-5-yl) methyl O 0 H H (4,5-dihydro-1,4,4-trimethyl- H CH.sub.3 OCH.sub.3 CH 1H-imidazol-2-yl)methyl O 0 H H (4,5-dihydro-1,4,4-trimethyl- H OCH.sub.3 OCH.sub.3 CH 1H-imidazol-2-yl)methyl O 0 H H (1,2,5-thiadiazol-3-yl) methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (1,2,5-thiadiazol-3-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 4-(2,6-dimethylmorpholino) H CH.sub.3 OCH.sub.3 CH methyl O 0 H H 4-(2,6-dimethylmorpholino) H OCH.sub.3 OCH.sub.3 CH methyl O 0 H H (4,6-dimethoxy-1,3,5- H CH.sub.3 OCH.sub.3 CH triazin-2-yl)methyl O 0 H H (4,6-dimethoxy-1,3,5- H OCH.sub.3 OCH.sub.3 CH triazin-2-yl)methyl O 0 H H (4-dimethyamino-6- methylthio H CH.sub.3 OCH.sub.3 CH 1,3,5-triazin-2-yl)methyl O 0 H H (4-dimethyamino-6-methylthio H OCH.sub.3 OCH.sub.3 CH 1,3,5-triazin-2 -yl)methyl O 0 H H (cyclopentanon-2-yl)methyl H CH.sub.3 CH.sub.3 CH O 0 H H (cyclopentanon-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (cyclopent anon-2-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (cyclopentanon-2-yl)met hyl H Cl OCH.sub.3 CH O 0 H H (cyclopentanon-2-yl)methyl H CH.sub.3 OCH.sub.3 N O 0 H H (cyclopentanon-2-yl)methyl H OCH.sub.3 OCH.sub.3 N O 0 H H .gamma. butyryllactone-2-yl)- H CH.sub.3 CH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-2-yl)- H CH.sub.3 OCH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-2-yl)- H OCH.sub.3 OCH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-2-yl)- H Cl OCH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-2-yl)- H CH.sub.3 OCH.sub.3 N methyl O 0 H H .gamma. butyryllactone-2-yl)- H OCH.sub.3 OCH.sub.3 N methyl O 0 H H .gamma. butyryllactone-3-yl)- H CH.sub.3 CH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-3-yl)- H CH.sub.3 OCH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-3-yl)- H OCH.sub.3 OCH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-3-yl)- H Cl OCH.sub.3 CH methyl O 0 H H .gamma. butyryllactone-3-yl)- H CH.sub.3 OCH.sub.3 N methyl O 0 H H .gamma. butyryllactone-3-yl)- H OCH.sub.3 OCH.sub.3 N methyl O 0 H H cyclohexanon-2-yl)methyl H CH.sub.3 CH.sub.3 CH O 0 H H (cyclohexanon-2-y l)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (cyclohexanon-2-yl)methyl h OCH.sub.3 OCH.sub.3 CH O 0 H H (cyclohexanon-2-yl)methyl H Cl OCH.sub.3 CH O 0 H H (cyclohexanon-2-yl)methyl H CH.sub.3 OCH.sub.3 N O 0 H H (cyclohexanon-2-yl)methyl H OCH.sub.3 OCH.sub.3 N O 0 H H 2-chloro-6-fluo robenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 4-methylthiobenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 4-methylsulfonylbenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 1,1'-biphenylmethyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-phenoxybenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-[4-(2,2-dimethyl-1,3- H OCH.sub.3 OCH.sub.3 CH dioxolan-2-yl)methoxy]ethyl O 0 H H 4-(2,2-dimethyl-1,3- H OCH.sub.3 OCH.sub.3 CH dioxolan-2-yl)methoxy O 0 H H (2-methyl-1,3 -dioxolan-2- H CH.sub.3 OCH.sub.3 CH yl)methyl O 0 H H (2-methyl-1,3- dioxolan-2- H OCH.sub.3 OCH.sub.3 CH yl)methyl O 0 H H 2-(2-methyl-1, 3-dioxolan- H CH.sub.3 OCH.sub.3 CH 2-yl)methyl O 0 H H 2-(2-methyl-1 ,3-dioxolan- H OCH.sub.3 OCH.sub.3 CH 2-yl)methyl O 0 H H (1,3-dioxol an-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (1,3-dioxolan-2-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-(1,3-dioxolan-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-(1,3-dioxolan-2-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (1,3-dioxolan-2-yl)methyl H CH.sub.3 OCH.sub.3 CH O 0 H H (1,3-dioxolan-2-yl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-(2-tetrahydr opyranyloxy) H CH.sub.3 OCH.sub.3 CH ethyl O 0 H H 2-(2-tetrahydropyr anyloxy) H OCH.sub.3 OCH.sub.3 CH ethyl O 0 H H CH.sub.2 C(CH.sub.3)NOH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NOH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHC(CH.sub.3)NOH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHC(CH.sub.3)NOH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)(CN)OSi(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH(C.sub.6 H.sub.5).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH(C.sub.6 H.sub.5).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH(CN).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH(CN).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H C(Cl)CHCl H CH.sub.3 OCH.sub.3 CH O 0 H H C(Cl)CHCl H OCH.sub.3 OCH.sub.3 CH O 0 H H CHCHC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH OO 0 H H CHCHCN H OCH.sub.3 OCH.sub.3 CH O 0 H H CHCHCO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CHCHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CHCHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CHCHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CHCHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-epoxypropyl H CH.sub.3 CH.sub.3 CH O 0 H H 2-epoxypropyl H Cl OCH.sub.3 CH O 0 H H 2-epoxypropyl H CH.sub.3 OCH.sub.3 N O 0 H H 2-epoxypropyl H OCH.sub.3 OCH.sub.3 N O 0 H H 2-epoxtbutyl H CH.sub.3 CH.sub.3 CH O 0 H H 2-epoxybutyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-epoxybutyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-epoxybutyl H Cl OCH.sub.3 CH O 0 H H 2-epoxybutyl H CH.sub.3 OCH.sub.3 N O 0 H H 2-epoxybutyl H OCH.sub.3 OCH.sub.3 N O 0 H H (4-t-butylcyclohexyl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H (4-chlorocyclopentyl)methyl H OCH.sub.3 OCH.sub.3 CH O 0 H H C.sub.6 H.sub.5 H CH.sub.3 CH.sub.3 CH O 0 H H C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H C.sub.6 H.sub.5 H Cl OCH.sub.3 CH O 0 H H C.sub.6 H.sub.5 H CH.sub. 3 OCH.sub.3 N O 0 H H C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 N O 0 H H .sub.--PNO.sub.2 C.sub.6 H.sub.4 H CH.sub.3 OCH.sub.3 CH O 0 H H N .sub.--PO.sub.2 C.sub.6 H.sub.4 H OCH.sub.3 OCH.sub.3 CH 193-194 O 0 H H .sub.--PCNC.sub.6 H.sub.4 H CH.sub.3 OCH.sub.3 CH O 0 H H .sub.--PCNC.sub.6 H.sub.4 H OCH.sub.3 OCH.sub.3 CH O 0 H H .sub.--PCH.sub.3 SO.sub.2 C.sub.6 H.sub.4 H CH.sub.3 OCH.sub.3 CH O 0 H H .sub.--PCH.sub.3 SO.sub.2 C.sub.6 H.sub.4 H OCH.sub.3 OCH.sub.3 CH O 0 H H .sub.--PClC.sub.6 H.sub.4 H CH.sub.3 OCH.sub.3 CH O 0 H H .sub.--PClC.sub.6 H.sub.4 H OCH.sub.3 OCH.sub.3 CH O 0 H H 4-pyrimidinyl H CH.sub.3 OCH.sub.3 CH O 0 H H 4-pyrimidinyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-pyrimidinyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-pyrimidinyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-thienyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-thienyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-thiazolyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 1-methyl-1H-imidazol-2-yl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-oxazolyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-(5-nitrothienyl) H CH.sub.3 OCH.sub.3 CH O 0 H H pyrimidin-2-yl H CH.sub.3 OCH.sub.3 CH O 0 H H 4,6-dimethoxypy rimidin- H CH.sub.3 OCH.sub.3 CH 2-yl O 0 H H 2-cyclopentanonyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-cyclopentanonyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-cyclopentanonyl H CH.sub.3 OCH.sub.3 CH O 0 H H 3-cyclopentanon yl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-cyclohexanonyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-cyclohexanonyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-cyclohexa nonyl H CH.sub.3 OCH.sub.3 CH O 0 H H 3-cyclohexanonyl H OCH.sub.3 OCH.sub.3 CH O 0 H H .gamma. butyrolactone- H CH.sub.3 OCH.sub.3 CH 2-yl O 0 H H .gamma. butyrolactone- H OCH.sub.3 OCH.sub.3 CH 206-211 2-yl O 0 H H .gamma. butyrolactone- H CH.sub.3 OCH.sub.3 CH 3-yl O 0 H H .gamma. butyrolactone- H OCH.sub.3 OCH.sub.3 CH 3-yl O 0 H H SCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H SCH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H SCH.sub.2 CH.sub.2 CH.sub.3 CH H OCH.sub.3 OCH.sub.3 CH O 0 H H S(CH.sub.2).sub.9 CH H OCH.sub.3 OCH.sub.3 CH O 0 H H SCCl.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H SCCl.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H SCCl.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H SCCl.sub. 3 H Cl OCH.sub.3 CH O 0 H H SCCl.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H SCCl.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H SC.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H SC.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H 4-nitrophenylthio H CH.sub.3 OCH.sub.3 CH O 0 H H 4-nitrophenylthio H OCH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H SO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H SO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H SO.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H phenylsulfonyl H CH.sub.3 OCH.sub.3 CH O 0 H H phenylsulfonyl H OCH.sub.3 OCH.sub.3 CH O 0 H H OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H OCH.sub.3 H Cl OCH.sub.3 CH O 0 H H OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H OH H CH.sub.3 OCH.sub.3 N O 0 H H OH H OCH.sub.3 OCH.sub.3 N O 0 H H OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H C(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH 227-228 O 0 H H C(O)CH.sub.3 H Cl OCH.sub.3 CH 218-220 O 0 H H C(O)CH.sub.3 H Br OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N 195-197 O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N 199-201 O 0 H H C(O)CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 190-191 O 0 H H C(O)CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 203-205 O 0 H H C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 185-186 O 0 H H C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 189-190 O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 196-198 O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 203-205 O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 185-186 O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 170-171 O 0 H H C(O)C.sub.6 H.sub.5 H CH.sub.3 CH.sub.3 CH O 0 H H C(O)C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)C.sub.6 H.sub.5 H Cl OCH.sub.3 CH O 0 H H C(O)C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)C.sub. 6 H.sub.5 H CH.sub.3 OCH.sub.3 CH 88, dec. O 0 H H C(O)CH.sub.2 C.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 N O 0 H H C(O)CH.sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 N O 0 H H C(O)thienyl H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)thienyl H OCH.sub.3 OCH.sub.3 CH O 0 H H CO.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 210-215 O 0 H H CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 171-173 O H H H CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 190-195 O 0 H H CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 143-150 O H H H CO.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CO.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O H H H CO.sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CO.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 CH O 0 H H CO.sub.2 CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)NHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)NHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)NHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)NHCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)NHCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)NH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O H H H C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 202-212 O H H H C(O)NH(cyclohexyl) H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)NH(cyclohexyl) H OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)NHC.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)NHC.sub.6 H.sub. 5 H OCH.sub.3 OCH.sub.3 CH O 0 H H (4,6-dimethylpyrimidin- H CH.sub.3 CH.sub.3 CH 181-183 2-yl)aminocarbonyl O 0 H H (4-methoxy-6-methylpyr imidin- H CH.sub.3 OCH.sub.3 CH 2-yl)aminocarbonyl O 0 H H (4,6-dimet hoxypyrimidin- H OCH.sub.3 OCH.sub.3 CH 192-194 2-yl)aminocarbonyl O 0 H H (4-chloro-6-methoxypyrimidin- H Cl OCH.sub.3 CH 206-208 2-yl)aminocarbonyl O 0 H H (4-methoxy-6-methyl-1,3,5- H CH.sub.3 OCH.sub.3 CH triazin-2-yl)aminocarbonyl O 0 H H (4,6-dimethoxy-1,3,5- H OCH.sub.3 OCH.sub.3 N triazin-2-yl)aminocarbonyl O 0 H H CS.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CS.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CS.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CS.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CS.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CS.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H NH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H NH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H NHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H NHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H NHCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H NHCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H NHC.sub.6 H.sub.5 H CH.sub.3 OCH.sub.3 CH O 0 H H NHC.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H 4-chlorobenzyl H CH.sub.3 CH.sub.3 CH O 0 H H 4-chlorobenzyl H CH.sub.3 OCH.sub.3 CH O 0 H H 4-chlorobenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 4-chlorobenzyl H Cl OCH.sub.3 CH O 0 H H 4-chlorobenzyl H CH.sub.3 OCH.sub.3 N O 0 H H 4-chlorobenzyl H OCH.sub.3 OCH.sub.3 N O 0 H H 4-methylbenzyl H CH.sub.3 CH.sub.3 CH 194-197 O 0 H H 4-methylbenzyl H CH.sub.3 OCH.sub.3 CH 193-196 O 0 H H 4-methylbenzyl H OCH.sub.3 OCH.sub.3 170-173 O 0 H H 4-methylbenzyl H Cl OCH.sub.3 CH 147-150 O 0 H H 4-methylbenzyl H CH.sub.3 OCH.sub.3 N 154-157 O 0 H H 4-methylbenzyl H OCH.sub.3 OCH.sub.3 N 139-143 O 0 H H 4-nitrobenzyl H CH.sub.3 CH.sub.3 CH 223-225 O 0 H H 4-nitrobenzyl H CH.sub.3 OCH.sub.3 CH 218-219 O 0 H H 4-nitrobenzyl H OCH.sub.3 OCH.sub.3 CH 180-183 O 0 H H 4-nitrobenzyl H Cl OCH.sub.3 CH 200-203 O 0 H H 4-nitrobenzyl H CH.sub.3 OCH.sub.3 N 189-192 O 0 H H 4-nitrobenzyl H OCH.sub.3 OCH.sub.3 N 198-200 O 0 H H 3-trifluoromethylbenzyl H CH.sub.3 CH.sub.3 CH O 0 H H 3-trifluoromethylb enzyl H CH.sub.3 OCH.sub.3 CH O 0 H H 3-trifluoromethylbenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-trifluoeomethylbenzyl H Cl OCH.sub.3 CH O 0 H H 3-trifluoromethylbenzyl H CH.sub.3 OCH.sub.3 N O 0 H H 3-trifluoromethylb enzyl H OCH.sub.3 OCH.sub.3 N O 0 H H 3-methylbenzyl H CH.sub.3 CH.sub.3 CH O 0 H H 3-methylbenzyl H CH.sub.3 OCH.sub.3 CH O 0 H H 3-methylbenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-methylbenzyl H Cl OCH.sub.3 CH O 0 H H 3-methylbenzyl H CH.sub.3 OCH.sub.3 N O 0 H H 3-methylbenzyl H OCH.sub.3 OCH.sub.3 N O 0 H H 2-methylbenzyl H CH.sub.3 CH.sub.3 CH O 0 H H 2-methylbenzyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-methylbenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-methylbenzyl H Cl OCH.sub.3 CH O 0 H H 2-methylbenzyl H CH.sub.3 OCH.sub.3 N O 0 H H 2-methylbenzyl H OCH.sub.3 OCH.sub.3 N O 0 H H OH H CH.sub.3 OCH.sub.3 CH O 0 H H OH H OCH.sub.3 OCH.sub.3 CH O 0 H H CN H CH.sub.3 CH.sub.3 CH O 0 H H CN H CH.sub.3 OCH.sub.3 CH O 0 H H CN H OCH.sub.3 OCH.sub.3 CH O 0 H H CN H Cl OCH.sub.3 CH O 0 H H CN H CH.sub.3 OCH.sub.3 N O 0 H H CN H CH.sub.3 OCH.sub.3 N O 0 H H P(O)(OCH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H P(O)(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H P(O)(OCH.sub.3).sub .2 H OCH.sub.3 OCH.sub.3 CH O 0 H H P(O)(OCH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H P(O)(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H P(O)(OCH. sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H P(O)(OCH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H P(S)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H P(O)(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H P(S)(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H P(O)(S CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H Si(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H Si(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H Si(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H Si(CH.sub.3). sub.3 H Cl OCH.sub.3 CH O 0 H H Si(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H Si(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H Si(CH.sub.3) .sub.2 C(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H Cl OCH.sub.3 CH O 0 H H Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H Si(CH.sub.3).sub.2 C.sub.6 H.sub.5 H OCH.sub.3 OCH.sub.3 CH O 0 H H Si(CH.sub.3).sub.2 (CH.sub.2).sub.9 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH S O H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH S O H H CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH S O H H CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH S O H H CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH S O H H CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH S O H H CF.sub.2 H H OCH.sub.3 OCH.sub.3 CH S O H H SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H C(O)NHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CS.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H NH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 1 H H OH H OCH.sub.3 OCH.sub.3 O 1 H H P(O)(OCH. sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 1 H H Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 SCN H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 1 H H CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H H OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH(CH.sub.3).sub.2 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH.sub.2 CF.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 Cl OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 Br OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 CH.sub.2 Cl OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH SCH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH SCH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH SCH.sub.2 CH.sub.3 Cl O 0 H H C(O)CH.sub.3 CH F OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH Cl OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH Br OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH.sub.2 CH.sub.2 F OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 OCH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH.sub.2 OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH OCH.sub.2 CH.sub.2 OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH NH.sub.2 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH NHCH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH NHCH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH NHCH(CH.sub.3).sub.2 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH NHCH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 CH N(CH.sub.3).sub.2 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H N(CH.sub.3)CH.sub.2 CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H N(CH.sub.3)C(CH.sub.3).sub.2 OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H cyclopropyl OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H cyclobutyl OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H cyclopentyl OCH.sub.3 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 H CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 CHCH.sub.2 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 C(CH.sub.3)CH.sub.2 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 CCH CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 CCCH.sub.3 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 CH.sub.2 SCH.sub.3 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 CH.sub.2 SC(CH.sub.3).sub.3 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 N.sub.3 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 CN CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 C(O)CH.sub.3 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 CHO CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 C(O)CH(CH.sub.3).sub.2 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 CH(OCH.sub.3).sub.2 CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 CH(OCH.sub.2 CH.sub.3).sub.2 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H SCH.sub.3 SCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H NHCH.sub.3 NHCH.sub.3 CH O 0 H H .sub.--m-CH.sub.3 C(O)CH.sub. 3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub. 3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.(CH.sub.3).sub.2 C(O)CH.sub .3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCF.sub.2 H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.2 CH.sub.2 CH.sub.2 F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CH.sub.2 Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CH.sub.2 CH.sub.2 F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.2 CH.sub.2 CH.sub.2 Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-NH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.-- m-NHCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-NHCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-NH(CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-NH CH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-NH CH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-N(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -p-F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -p-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-I C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-NO.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub. 3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 C(O)CH.sub. 3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub .3).sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F C(O)CH.su b.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-F C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub. 3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub. 3 CH O 0 H .sub.--m-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-F C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 C(O)CH.sub. 3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-F C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 C(O)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub. 3 CH O 0 H -o-Cl CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub. --m-SCH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H o --F CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub. 3 CH O 0 H -o-Br CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH .sub.3 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub. 2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CN H OCH.sub. 3 OCH.sub.3 CH O 0 H -o-F CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-F CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CN H OCH.sub.3 OCH.sub.3 CH O 0 H m .sub.---OCH.sub.2 CH.sub.3 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CN H OCH.sub.3 OCH.sub. 3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CN H OCH.sub. 3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub. 2 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub. 2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CCH H OCH.sub.3 OCH.sub. 3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.-- m-OCH.sub.2 CH.sub.3 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH
W n R R.sub.1 R.sub.2 R.sub.3 X Y Z m.p. (.degree.C.) O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-F CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-Br CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Br CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.-- m-CH.sub.3 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-F CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H o --F CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Br CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 NO.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH(CH.sub.3).sub.2 H H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 H H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH(CH.sub.3). sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH(CH.sub.3).sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub .2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 CH.sub.3 CH CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH(CH.sub.3). sub.2 CH CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH. sub.3).sub.2 CH CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H m .sub.---OCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-NHCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.2 CH.sub.2 F CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CCH H CH.sub.3 CH.sub.3 CH 206-209 O 0 H H CH.sub.2 CCH H Cl OCH.sub.3 CH 198-200 O 0 H H CH.sub.2 CCH H CH.sub. 3 OCH.sub.3 N 188-190 O 0 H H CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 N 190-192 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHCH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 204-204.5(d) O 0 H H CH.sub.2 CHCH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 205-208(d) O 0 H H CH.sub.2 CHCH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 224-226(d) O 0 H H CH.sub.2 CHCH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 214-215(d) O 0 H H CH.sub.2 CHCH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 183-185(d) O 0 H H CH.sub.2 CHCH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 170-173(d) O 0 H H C(O)CH.su b.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H C(O)CH.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H C(O)C(CH.sub.3).sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CO.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CO.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 C(O)CH.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CHCH.sub.2 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CCH H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 F H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 Cl H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 Br N OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CF.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 CHF.sub.2 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub. 2 CN H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.3 H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H CH.sub.2 Cl H OCH.sub.2 CH.sub.3 NHCH.sub.3 N O 0 H H C(O)CH.sub.3 H OCH.sub.3 H CH O 0 H H C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 H CH O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H CH O 0 H H C(O)C(CH.sub.3).sub.3 H OCH.sub.3 H CH O 0 H H CO.sub.2 CH.sub.3 H OCH.sub.3 H CH O 0 H H CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H CH O 0 H H CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H CH O 0 H H CO.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 H CH O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 H CH O 0 H H CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 H CH O 0 H H CH.sub.2 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 H CH O 0 H H CH.sub.2 CHCH.sub.2 H OCH.sub.3 H CH O 0 H H CH.sub.2 CCH H OCH.sub.3 H CH O 0 H H CH.sub.2 CH.sub.2 F H OCH.sub.3 H CH O 0 H H CH.sub.2 CH.sub.2 Cl H OCH.sub.3 H CH O 0 H H CH.sub.2 CH.sub.2 Br H OCH.sub.3 H CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 H CH O 0 H H CH.sub.2 CF.sub.3 H OCH.sub.3 H CH O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 H CH O 0 H H CH.sub.2 CHF.sub.2 H OCH.sub.3 H CH O 0 H H CH.sub.2 CN H OCH.sub.3 H CH O 0 H H CH.sub.2 OCH.sub.3 H OCH.sub.3 H CH O 0 H H CH.sub.2 Cl H OCH.sub.3 H CH O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H C(O)C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CO.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CH.sub.2 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CH.sub.2 C CH H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CH.sub.2 CN H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.2 CH.sub.2 F N O 0 H H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H C(O)C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CO.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CO.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CO.sub.2 C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 C(O)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CCH H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CH.sub.2 Br H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CF.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CHF.sub.2 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 CN H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H H CH.sub.2 Cl H OCH.sub.3 OCH.sub.2 CF.sub.3 N O 0 H .sub.--m-(CH.sub.2).sub.5 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-(CH.sub.2).sub.3 CH(CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m- (CH.sub.2).sub.5 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-O(CH.sub.2).sub.5 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-S(CH.sub.2).sub.5 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-S(O)(CH.sub.2).sub.5 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 (CH.sub.2).sub.5 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CN C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-O(CH.sub.2).sub.5 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-S(CH.sub.2).sub.5 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-NH(CH.sub.2 ).sub.5 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-N(CH.sub.3 )(CH.sub.2).sub.5 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 NH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 NH(CH.sub.2).sub.3 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 N(CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub. 2 N(CH.sub.3)OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 N(CH.sub.3)OCH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 N(CH.sub.3)CH.sub.2 CN C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 NH(CH.sub.2).sub.3 CN C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-SO.sub.2 NHCH.sub.2 C CHH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-azetidinyl- C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH sulfonyl O 0 H -o-pyrrolidinyl- C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH sulfonyl O 0 H -o-piperidinyl- C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH sulfonyl O 0 H -o-morpholino- C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH sulfonyl O 0 H .sub.--m-CH.sub.2 OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-(CH.sub.2 ).sub.3 OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 SCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 S(CH.sub.2).sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 S(O)Pr C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 SO.sub.2 Pr C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH .sub.2 SO.sub.2 NHPr C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 N(CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 NHPr C(O)CH.sub.3 H OCH.sub. 3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 NO.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-(CH.sub.2).sub.3 NO.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CN C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-(CH.sub.2).sub.3 CN C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CO.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-(CH.sub.2).sub.2 CO.sub.2 H C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 CO.sub.2 Pr C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 O(CH.sub.2).sub.2 F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H - o-CH.sub.2 O(CH.sub.2).sub.2 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CH.sub.2 OCH.sub.2 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 O(CH.sub.2).sub.3 Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-(CH.sub.2).sub.2 S(CH.sub.2).sub.2 Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.2 Ph C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 (CH.sub.2).sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 CH.sub.2 CHCH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 (CH.sub.2).sub.2 CHCH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H o --CO.sub.2 CH.sub.2 CCCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 CH.sub.2 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 (CH.sub.2).sub.4 Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 CH.sub.2 CN C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 (CH.sub.2).sub.3 CN C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 -cyclopentyl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 -cyclopentyl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 -cyclopropyl- C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH methyl O 0 H -o-CO.sub.2 -cyclohexyl- C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH methyl O 0 H -o-CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CO.sub.2 (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CN CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CN CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CN CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CN CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CN CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CN CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CH.sub.2 OCH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 OCH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 OCH.sub.3 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H o --Si(CH.sub.3).sub.3 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CH.sub.2 SCH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 SCH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 SCH.sub.3 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CH.sub.2 CN CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CN CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CN CH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--m-CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-Si(CH.sub.3).sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CH.sub.2 SCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 SCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 SCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H -o-CH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H -o-CH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.3 H Cl OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.3 H Br OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H (CO).sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H (CO).sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H (CO).sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H (CO).sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H (CO).sub.2 OPh H CH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 OPh H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SeCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SeCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 SeCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SePh H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SePh H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SePh H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SePh H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SePh H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SePh H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SePh H OCH.sub.3 OCH.sub.3 N O 0 H H (CO).sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 Ph H CH.sub.3 OCH.sub.3 CH O 0 H H (CO).sub.2 Ph H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-thienoyl H CH.sub.3 CH.sub.3 CH O 0 H H 2-thienoyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-thienoyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-thienoyl H Cl OCH.sub.3 CH O 0 H H 2-thienoyl H Br OCH.sub.3 CH O 0 H H 2-thienoyl H CH.sub.3 OCH.sub.3 N O 0 H H 2-thienoyl H OCH.sub.3 OCH.sub.3 N O 0 H H 3-thienoyl H CH.sub.3 CH.sub.3 CH O 0 H H 3-thienoyl H CH.sub.3 OCH.sub.3 CH O 0 H H 3-thienoyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-thienoyl H Cl OCH.sub.3 CH O 0 H H 3-thienoyl H Br OCH.sub.3 CH O 0 H H 3-thienoyl H CH.sub.3 OCH.sub.3 N O 0 H H 3-thienoyl H OCH.sub.3 OCH.sub.3 N O 0 H H 2-furoyl H CH.sub.3 CH.sub.3 CH O 0 H H 2-furoyl H CH.sub. OCH.sub.3 CH O 0 H H 2-furoyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-furoyl H Cl OCH.sub.3 CH O 0 H H 2-furoyl H Br OCH.sub.3 CH O 0 H H 2-furoyl H CH.sub.3 OCH.sub.3 N O 0 H H 2-furoyl H OCH.sub.3 OCH.sub.3 N O 0 H H 3-furoyl H CH.sub.3 CH.sub.3 CH O 0 H H 3-furoyl H CH.sub.3 OCH.sub.3 CH O 0 H H 3-furoyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-furoyl H Cl OCH.sub.3 CH O 0 H H 3-furoyl H Br OCH.sub.3 CH O 0 H H 3-furoyl H CH.sub.3 OCH.sub.3 N O 0 H H 3-furoyl H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 -pyri- H OCH.sub.3 OCH.sub.3 CH dinium bromide O 0 H H C(O)C(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH 176-178 O 0 H H C(O)C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH 201-202 O 0 H H C(O)C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH 203-204 O 0 H H C(O)C(CH.sub.3).sub.3 H Cl OCH.sub.3 CH 199-200 O 0 H H C(O)C(CH.sub.3).sub.3 H Br OCH.sub.3 CH O 0 H H C(O)C(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H C(O)C(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H C(O)CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H C(O)CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH.sub.2 CH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H C(O)CH.sub.2 CH(CH.sub.3).sub.2 H Br OCH.sub.3 CH O 0 H H C(O)CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H C(O)CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H C(O)CH(CH.sub.3).sub. 2 H CH.sub.3 OCH.sub.3 CH O 0 H H C(O)CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(Br)CH.sub.2 H CH.sub.3 CH.sub.3 CH 220-222 O 0 H H CH.sub.2 C(Br)CH.sub.2 H CH.sub.3 OCH.sub.3 CH 213-214 O 0 H H CH.sub.2 C(Br)CH.sub.2 H OCH.sub.3 OCH.sub.3 CH 211-213 O 0 H H CH.sub.2 C(Br)CH.sub.2 H Cl OCH.sub.3 CH 188-190 O 0 H H CH.sub.2 C(Br)CH.sub.2 H Br OCH.sub.3 CH O 0 H H CH.sub.2 C(Br)CH.sub.2 H CH.sub.3 OCH.sub.3 N 190-192 O 0 H H CH.sub.2 C(Br)CH.sub.2 H OCH.sub.3 OCH.sub.3 N 184-185 O 0 H H CHCH.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CHCH.sub.2 H Cl OCH.sub.3 CH O 0 H H CHCH.sub.2 H Br OCH.sub.3 CH O 0 H H CHCH.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CHCH.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 207-208 O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 149-150 O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 204-205 O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 212-214 O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H Br OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 197-198 O 0 H H CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 195-196 O 0 H H CH.sub.2 CHF.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CHF.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHF.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHF.sub.2 H Cl CH.sub.3 CH O 0 H H CH.sub.2 CHF.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHF.sub.2 H OCH.sub. 3 OCH.sub.3 N O 0 H H CH.sub.2 CHCl.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CHCl.sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CHCl.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHCl.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 OCH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OCH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 OCH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OCH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OC(CH.sub.3).sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 OC(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 OC(CH.sub.3).sub.3 H OCH.sub. 3 OCH.sub.3 CH O 0 H H CH.sub.2 OC(CH.sub.3).sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 OC(CH.sub.3).sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 OC(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SPh H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SPh H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SPh H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SPh H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 SPh H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 SPh H OCH.sub.3 OCH.sub.3 N O 0 H H N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H N(CH.sub. 3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H cyclopropyl H CH.sub.3 CH.sub.3 CH O 0 H H cyclopropyl H CH.sub.3 OCH.sub.3 CH O 0 H H cyclopropyl H OCH.sub.3 OCH.sub.3 CH O 0 H H cyclopropyl H Cl OCH.sub.3 CH O 0 H H cyclopropyl H CH.sub.3 OCH.sub.3 N O 0 H H cyclopropyl H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OH H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OH H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OC(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub. 2 CH(CH.sub.3)OC(O)CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OSO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OSO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.3)OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.3)OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 CH.sub.3 OH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH 170-173 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 199-201 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H Cl OCH.sub.3 CH 196-198 O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OH H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OH H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OH H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OH H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub. 2 CH.sub.3)OC(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OC(O)CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OSO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OSO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OSO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH(CH.sub.2 CH.sub.3)OSO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CCH H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CCH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CCH H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CCH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CCCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CCCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CCCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C CCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH(CH.sub.3)CCH H CH.sub.3 CH.sub.3 CH O 0 H H CH(CH.sub.3)CCH H Cl OCH.sub.3 CH O 0 H H CH(CH.sub.3 )CCH H CH.sub.3 OCH.sub.3 N O 0 H H CH(CH.sub.3)CCH H OCH.sub.3 OCH.sub.3 N O 0 H H 3-epoxybutyl H CH.sub.3 CH.sub.3 CH O 0 H H 3-epoxybutyl H CH.sub.3 OCH.sub.3 CH O 0 H H 3-epoxybutyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 3-epoxybutyl H Cl OCH.sub.3 CH O 0 H H 3-epoxybutyl H CH.sub.3 OCH.sub.3 N O 0 H H 3-epoxybutyl H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NH.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NH.sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NH.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NH.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub. 2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NHC(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHC(O)CH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHC(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NHC(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NHCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHCH.sub.3 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 NHCH.sub.3 H CH.sub. 3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 NHCH.sub.3 H OCH.sub.3 OCH.sub.3 O 0 H H CH.sub.2 C(CH.sub.3)NOH H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NOH H Cl OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NOH H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(CH.sub.3)NOH H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(CH.sub.3)NNH.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 N C(CH.sub.3)NH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 N C(CH.sub.3)NH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNH.sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNH.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 N C(CH.sub.3)NH.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 N C(CH.sub.3)NHPh H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNHPh H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNHPh H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNHPh H Cl OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNHPh H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(CH.sub.3)NNHPh H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 C(CH.sub.3)NNHCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNHCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNHCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 C(CH.sub.3)NNHCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 H CL OCH.sub.3 CH O 0 H H CH.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 SCN H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 SCN H Cl OCH.sub.3 CH O 0 H H CH.sub.2 SCN H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 SCN H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CO.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CO.sub. 2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H H cyclopentanone-3-yl H CH.sub.3 CH.sub.3 CH O 0 H H cyclopentanone-3-y l H CH.sub.3 OCH.sub.3 CH O 0 H H cyclopentanone-3-yl H OCH.sub.3 OCH.sub.3 CH O 0 H H cyclopentanone-3-yl H Cl OCH.sub.3 CH O 0 H H cyclopentanone-3-yl H CH.sub.3 OCH.sub.3 N O 0 H H cyclopentanone-3-yl H OCH.sub.3 OCH.sub.3 N O 0 H H cyclohexanone-3-yl H CH.sub.3 CH.sub.3 CH O 0 H H cyclohexanone-3-yl H CH.sub.3 OCH.sub.3 CH O 0 H H cyclohexanone- 3-yl H OCH.sub.3 OCH.sub.3 CH O 0 H H cyclohexanone-3-yl H Cl OCH.sub.3 CH O 0 H H cyclohexanone-3-yl H CH.sub.3 OCH.sub.3 N O 0 H H cyclohexanon e-3-yl H OCH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHCHCCC(CH.sub.3).sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHCHCHCH.sub.2 H CH.sub.3 CH.sub.3 CH O 0 H H CH.sub.2 CHCHCHCH.sub.2 H CH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHCHCHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH O 0 H H CH.sub.2 CHCHCHCH.sub.2 H Cl OCH.sub.3 CH O 0 H H CH.sub.2 CHCHCHCH.sub.2 H CH.sub.3 OCH.sub.3 N O 0 H H CH.sub.2 CHCHCHCH.sub.2 H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl C(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--m-Cl C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl CH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--m-Cl CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH 188-193 O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH 199-124 O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N 164-172 O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N 153-158 O 0 H p .sub.---CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H .sub.--p-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--p-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--p-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--p-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--p-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-SO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-SO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 CH O 0 H .sub. --m-SO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-SO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-SO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-SO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-CF.sub.3 C(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH O 0 H .sub.--m-CF.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 C(O)CH.sub.3 H Cl OCH.sub.3 CH O 0 H .sub.--m-CF.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N O 0 H .sub.--m-CF .sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N O 0 H H CF.sub.2 CF.sub.2 H H CH.sub.3 CH.sub.3 CH O 0 H H CF.sub.2 CF.sub.2 H H Cl OCH.sub.3 CH O 0 H H CF.sub.2 CF.sub.2 H H CH.sub.3 OCH.sub.3 N O 0 H H CF.sub.2 CF.sub.2 H H OCH.sub.3 OCH.sub.3 N O 0 H H CH(CH.sub.3)CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 214-216 O 0 H H CH(CH.sub.3)CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 230-233 O 0 H H CH(CH.sub.3)CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 228-231 O 0 H H CH(CH.sub.3)CH(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 224-272 O 0 H H CH(CH.sub.3)CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 167-170 O 0 H H CH(CH.sub.3)CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 130-133 O 0 H H cyclohexyl H CH.sub.3 CH.sub.3 CH 168-171 O 0 H H cyclohexyl H Cl OCH.sub.3 CH 224-227 O 0 H H cyclohexyl H CH.sub.3 OCH.sub.3 N 139-142 O 0 H H cyclohexyl H OCH.sub.3 OCH.sub.3 N 184-187 O 0 H H cyclopropyl H CH.sub.3 CH.sub. 3 CH O 0 H H cyclopropyl H Cl OCH.sub.3 CH O 0 H H cyclopropyl H OCH.sub.3 OCH.sub.3 N O 0 H H 2-fluorobenzyl H CH.sub.3 CH.sub.3 CH 180-183 O 0 H H 2-fluorobenzyl H CH.sub.3 OCH.sub.3 182-185 O 0 H H 2-fluorobenzyl H Cl OCH.sub.3 CH 180-183 O 0 H H 2-fluorobenzyl H CH.sub.3 OCH.sub.3 N 172-174 O 0 H H 2-fluorobenzyl H OCH.sub.3 OCH.sub.3 N 173-175 O 0 H H 2-chlorobenzyl H CH.sub.3 CH.sub.3 CH 194-197 O 0 H H 2-chlorobenzyl H CH.sub.3 OCH.sub.3 CH 178-180 O 0 H H 2-chlorobenzyl H OCH.sub.3 OCH.sub.3 CH 200-203 O 0 H H 2-chlorobenzyl H Cl OCH.sub.3 CH 194-197 O 0 H H 2-chlorobenzyl H CH.sub.3 OCH.sub.3 N 180-182 O 0 H H 2-chlorobenzyl H OCH.sub.3 OCH.sub.3 N 163-166 O 0 H H 2-bromobenzyl H CH.sub.3 CH.sub.3 CH O 0 H H 2-bromobe nzyl H CH.sub.3 OCH.sub.3 CH O 0 H H 2-bromobenzyl H OCH.sub.3 OCH.sub.3 CH O 0 H H 2-bromobenzyl H Cl OCH.sub.3 CH O 0 H H 2-bromobenzyl H CH.sub.3 OCH.sub.3 N O 0 H H 2-bromobenzyl H OCH.sub.3 OCH.sub.3 N O 0 H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-SCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-CN CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-F CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-Cl CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-SCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-F CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH O 0 H -o-CN CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH 0 1 H H CH.sub.2 CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH 0 1 H H CH.sub.2 CH.sub.2 F H Cl OCH.sub.3 CH 0 1 H H CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CH 0 1 H H CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 CH
TABLE Ib__________________________________________________________________________ ##STR74##W R R.sub.1.sup.' R.sub.2 R.sub.4.sup.' X Y Z m.p. (.degree.C.)__________________________________________________________________________O H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 F H CH.sub.3 CH.sub.3 CHO H H CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 F H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 F H CH.sub.3 OCH.sub.3 NO H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CHO H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NO H H CH.sub.3 CH.sub.3 Cl OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 Br OCH.sub.3 CHO H H CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H Ch.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H o-CH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CHO H m-CH.sub.2 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-CH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 NO H o-OCH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CHO H m-OCH.sub.2 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-OCH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 Cl OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 Br OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 Cl OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 Br OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 NO H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 CHO H o-CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-CH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-OCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-OCH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-OCH.sub.2 CH.sub.2 CH.sub.2 Cl C(O)CH.sub.3 H OCH.sub. 3 OCH.sub.3 CHO H o-CH.sub.2 CH.sub.2 Br C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-CH.sub.2 CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-CF.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-CH.sub.2 CH.sub.2 CH.sub.2 F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-SCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-SCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-SCH.sub.2 CH.sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-SCH.sub.2 CH.sub.2 CH.sub.2 F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-NH.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-NHCH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-N(CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-NH(CH.sub.2).sub.2 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-N(CH.sub.2 CH.sub.2 CH.sub.3).sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H p-Cl C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H p-F C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-Br C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-Br C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H o-NO.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H m-NO.sub.2 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE Ic__________________________________________________________________________ ##STR75##W R R.sub.1 R.sub.2 R.sub.4 X Y Z m.p. (.degree.C.)__________________________________________________________________________O H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CHO H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 NO H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub. 3 NO H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NO H H CH.sub.3 CH.sub.3 Cl OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 Br OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2 CHO H H CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH(CH.sub.3)CH.sub.2 CH.sub.3 OCH.sub. 3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CHO H H CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH.sub.3 CH.sub.3 Cl OCH.sub.3 CHO H H CH.sub.2 CH.sub.3 CH.sub.3 Br OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub. 3 OCH.sub.3 NO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 Cl OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 Br OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 NO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 Cl OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 Br OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 OCH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 OCH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 SCH.sub.3 H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 SCH.sub.3 H OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CN H CH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CN H OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Cl CH.sub.2 CH.sub.2 CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-Br CH.sub.2 CH.sub.2 CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H .sub.--m-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-Cl CH.sub.2 CH.sub.2 CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H -o-CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 cyclopropyl OCH.sub.3 CHO H H CH.sub.3 CH.sub.3 cyclopropyl OCH.sub.3 NO H H C(O)CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H C(O)CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H C(O)CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 F CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 CH.sub.2 F CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 CH.sub.2 Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CHO H H CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE Id__________________________________________________________________________ ##STR76## R.sub.1 or m.p.W.sub.2 W.sub.1 J n R R.sup.1.sup.' R.sub.3 R.sub.5 R.sub.6 R.sub.7 X Y Z (.degree.C.)__________________________________________________________________________-- S J-5 0 H H H H -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub.2 CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub. 2 CH.sub.2 CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH(CH.sub.3).sub.2 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub.2 CH(CH.sub.3).sub.2 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH(CH.sub.2)CH.sub.2 CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H C(CH.sub.3).sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub.3 -- -- CH.sub.3 CH.sub.3 CH-- S J-5 0 H H H CH.sub.3 -- -- CH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 0 H H H CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 N-- S J-5 1 H H H CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 1 H H H CH.sub.2 CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 1 H H H CH.sub.2 CH.sub.2 CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 1 H H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-5 1 H H H CH.sub.2 CH(CH.sub.3).sub.2 -- -- OCH.sub.3 OCH.sub.3 CHO S J-6 0 H H H -- -- -- CH.sub.3 CH.sub.3 CHO S J-6 0 H H H -- -- -- CH.sub.3 OCH.sub.3 CHO S J-6 0 H H H -- -- -- OCH.sub.3 OCH.sub.3 CHO S J-6 0 H H H -- -- -- CH.sub.3 CH.sub.3 NO S J-6 0 H H H -- -- -- CH.sub. 3 OCH.sub.3 NO S J-6 0 H H H -- -- -- OCH.sub.3 OCH.sub.3 NO S J-6 0 H H H -- -- -- Cl OCH.sub.3 CHO S J-6 0 H H H -- -- -- Br OCH.sub.3 CHO S J-6 1 H H H -- -- -- CH.sub.3 CH.sub.3 CHO S J-6 1 H H H -- -- -- CH.sub.3 OCH.sub.3 CHO S J-6 1 H H H -- -- -- OCH.sub.3 OCH.sub.3 CHO S J-6 1 H H H -- -- -- CH.sub.3 CH.sub.3 NO S J-6 1 H H H -- -- -- CH.sub.3 OCH.sub.3 NO S J-6 1 H H H -- -- -- OCH.sub.3 OCH.sub.3 NO S J-6 1 H H H -- -- -- Cl OCH.sub.3 CHO S J-6 1 H H H -- -- -- Br OCH.sub.3 CH-- S J-7 0 H H H H -- -- OCH.sub.3 OCH.sub.3 CH-- S J-7 0 H H H CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-7 1 H H H H -- -- OCH.sub.3 OCH.sub.3 CH-- S J-7 1 H H H CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-8 -- H H -- H -- -- OCH.sub.3 OCH.sub.3 CH-- S J-8 -- H H -- CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CH-- S J-9 -- H H -- H -- -- OCH.sub.3 OCH.sub.3 CH-- S J-9 -- H H -- CH.sub.3 -- -- OCH.sub.3 OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.3 CH.sub.3 CH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.3 CH.sub.3 OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.3 OCH.sub.3 OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.3 CH.sub.3 OCH.sub.3 NO S J-10 -- H H -- -- H CH.sub.3 OCH.sub.3 OCH.sub.3 NO S J-10 -- H H -- -- H CH.sub.3 Cl OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.3 Br OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO S J-10 -- H H -- -- H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CHO S J-10 -- H H -- -- CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHS S J-10 -- H H -- -- H CH.sub.3 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE Ie__________________________________________________________________________ ##STR77## m.p.J W.sub.2 m' n R R.sub.1.sup.' R.sub.4 R.sub.5 R.sub.6 X Y Z (.degree.C.)__________________________________________________________________________J-11 O -- 0 H H CH.sub.3 H H OCH.sub.3 OCH.sub.3 CHJ-11 O -- 0 H H CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CHJ-11 O -- 1 H H CH.sub.3 H H OCH.sub.3 OCH.sub.3 CHJ-11 O -- 1 H H CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CHJ-11 S -- 0 H H CH.sub.3 H H OCH.sub.3 OCH.sub.3 CHJ-12 O 1 0 H H -- H H OCH.sub.3 OCH.sub.3 CHJ-12 O 2 0 H H -- H H OCH.sub.3 OCH.sub.3 CHJ-12 S 1 0 H H -- H H OCH.sub.3 OCH.sub.3 CHJ-11 O -- 0 H H Butyl H H OCH.sub.3 OCH.sub.3 CHJ-11 O -- 0 H H CH.sub.3 Butyl H OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE IIa__________________________________________________________________________ ##STR78## R.sub.1 ' or m.p.J n R R.sub.1 R.sub.2 R.sub.3 R.sub.4 X.sub.1 Y.sub.1 m (.degree.C.)__________________________________________________________________________J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.2 CH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCF.sub.2 H CH.sub.2 1J-1 0 H H CH.sub. 2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.2 CH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCF.sub.2 H O 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.2 CH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCF.sub.2 H O 2J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H -- OCH.sub.3 CH.sub.2 1J-1 0 H H CH.sub.2 C(CH.sub.3 )CH.sub.2 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H -- OCH.sub.3 O 2J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 CH.sub.2 1J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 O 1J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H -o-OCH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 CH.sub.2 1J-1 0 H -o-OCH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 O 1J-1 0 H -o-OCH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCH.sub. 3 O 1J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3 O 2J-1 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H -- OCH.sub.3 O 1J-1 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H -- OCH.sub.3 O 2J-4 -- H H H -- CH.sub.3 OCH.sub.3 O 1J-4 -- H H CH.sub.3 -- CH.sub.3 OCH.sub. 3 O 1J-4 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-4 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 OCH.sub.3 O 1J-2 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-2 -- H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-2 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- CH.sub.3 OCH.sub.3 O 1J-2 -- H H CH.sub.2 C(CH.sub.3)CH.sub.2 -- CH.sub.3 OCH.sub.3 O 1J-3 -- H H CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-3 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 O 1J-3 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 OCH.sub.3 O 1J-1 O H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 O H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 O H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 O H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H -- OCH.sub.3 O 1J-1 O H .sub.--m-CH.sub.2 CH.sub.3 H H -- OCH.sub.3 O 1J-1 O H .sub.--m-OCH.sub.2 CH.sub.3 H H -- OCH.sub.3 O 1J-1 O H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 O 1J-1 O H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 O H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 O H -o-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 O 1J-1 O H -o-OCH.sub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H -- OCH.sub.3 O 1__________________________________________________________________________ * symbols -o and .sub.--m refer to ortho and meta to sulfonylurea bridge respectively.
TABLE IIb__________________________________________________________________________ ##STR79## R.sub.1 or m.p.W.sub.2 W.sub.1 J n R R.sub.1 ' R.sub.3 R.sub.5 R.sub.6 R.sub.7 X.sub.1 Y.sub.1 m (.degree.C.)__________________________________________________________________________-- S J-5 0 H H H H -- -- OCH.sub.3 O 1-- S J-5 0 H H H H -- -- OCH.sub.3 O 2-- S J-5 0 H H H CH.sub.3 -- -- OCH.sub.3 O 1-- S J-5 0 H H H CH.sub.3 -- -- OCH.sub.3 O 2-- S J-5 1 H H H CH.sub.3 -- -- OCH.sub.3 O 1-- S J-5 1 H H H CH.sub.3 -- -- OCH.sub.3 O 2O S J-6 0 H H H -- -- -- OCH.sub.3 O 1O S J-6 0 H H H -- -- -- OCH.sub.3 O 2O S J-6 1 H H H -- -- -- OCH.sub.3 O 1O S J-6 1 H H H -- -- -- OCH.sub.3 O 2-- S J-7 0 H H H H -- -- OCH.sub.3 O 1-- S J-7 0 H H H H -- -- OCH.sub.3 O 2-- S J-7 0 H H H CH.sub.3 -- -- OCH.sub.3 O 1-- S J-7 0 H H H CH.sub.3 -- -- OCH.sub.3 O 2-- S J-7 1 H H H CH.sub.3 -- -- OCH.sub.3 O 1-- S J-7 1 H H H CH.sub.3 -- -- OCH.sub.3 O 2-- S J-8 -- H H -- CH.sub.3 -- -- OCH.sub.3 O 1-- S J-8 -- H H -- CH.sub.3 -- -- OCH.sub.3 O 2-- S J-9 -- H H -- CH.sub.3 -- -- OCH.sub.3 O 1-- S J-9 -- H H -- CH.sub.3 -- -- OCH.sub.3 O 2O S J-10 -- H H -- -- H CH.sub.3 OCH.sub.3 O 1O S J-10 -- H H -- -- H CH.sub.3 OCH.sub.3 O 2O S J-10 -- H H -- -- H CH.sub.2 CH.sub.3 OCH.sub.3 O 1O S J-10 -- H H -- -- H CH.sub.2 CH.sub.3 OCH.sub.3 O 2O S J-10 -- H H -- -- CH.sub.3 CH.sub.3 OCH.sub.3 O 1O S J-10 -- H H -- -- CH.sub.3 CH.sub.3 OCH.sub.3 O 2O S J-6 1 H H H -- -- -- CH.sub.3 CH.sub.2 1O S J-6 1 H H H -- -- -- CH.sub.3 O 1O S J-6 1 H H H -- -- -- CH.sub.3 O 2O S J-6 1 H H H -- -- -- OCH.sub.3 CH.sub.2 1O S J-6 1 H H H -- -- -- OCH.sub.2 CH.sub.3 CH.sub.2 1O S J-6 1 H H H -- -- -- OCH.sub.2 CH.sub.3 O 1O S J-6 1 H H H -- -- -- OCH.sub.2 CH.sub.3 O 2O S J-6 1 H H H -- -- -- OCF.sub.2 H CH.sub.2 1O S J-6 1 H H H -- -- -- OCF.sub.2 H O 1O S J-6 1 H H H -- -- -- OCF.sub.2 H O 2S S J-6 1 H H H -- -- -- OCH.sub.3 O 1__________________________________________________________________________
TABLE IIc______________________________________ ##STR80## m.p.J W.sub.2 m' n R R.sub.1 ' R.sub.4 R.sub.5 R.sub.6 X.sub.1 Y.sub.1 m (.degree.C.)______________________________________J-11 O -- 0 H H CH.sub.3 H H OCH.sub.3 O 1J-11 O -- 1 H H CH.sub.3 H H OCH.sub.3 O 1J-11 S -- 0 H H CH.sub.3 H H OCH.sub.3 O 1J-11 S -- 1 H H CH.sub.3 H H OCH.sub.3 O 1J-12 O 1 0 H H -- H H OCH.sub.3 O 1J-12 O 2 0 H H -- H H OCH.sub. 3 O 1J-12 S 1 0 H H -- H H OCH.sub.3 O 1J-12 S 2 0 H H -- H H OCH.sub.3 O 1J-12 O 1 1 H H -- H H OCH.sub.3 O 1J-12 O 2 1 H H -- H H OCH.sub.3 O 1J-12 S 1 1 H H -- H H OCH.sub.3 O 1J-12 S 2 1 H H -- H H OCH.sub.3 O 1______________________________________
TABLE IIIa__________________________________________________________________________ ##STR81## R.sub.1 * or m.p.J n R R.sub.1 '* R.sub.2 R.sub.3 R.sub.4 X.sub.1 Y.sub.3 (.degree.C.)__________________________________________________________________________J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 HJ-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.2 CH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCF.sub.2 H CH.sub. 3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H -- OCH.sub.3 CH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H .sub.--m-CH.sub.2 CH.sub.3 CH.sub. 2 CH(CH.sub.3).sub.2 H -- OCH.sub.3 CH.sub.3J-1 0 H .sub.--m-CH.sub.2 CH.sub.3 H H -- OCH.sub.3 CH.sub.3J-1 0 H -o-OCH.sub.2 CH.sub.3 H H -- OCH.sub.3 CH.sub.3J-1 0 H -o-OCH.sub.2 CH.sub.3 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H -o-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 0 H .sub.--m-OCH.sub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H -- OCH.sub.3 CH.sub.3J-1 1 H H CH.sub.2 CH.sub.3 OCH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 1 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- OCH.sub.3 CH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3 CH.sub.3J-1 1 H H CH.sub.2 C(CH.sub.3)CH.sub.2 H -- OCH.sub.3 CH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- -- OCH.sub.3 CH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 -- -- OCH.sub.3 CH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- -- OCH.sub.3 CH.sub.3J-2 -- H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 -- -- OCH.sub.3 CH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- -- OCH.sub.3 CH.sub.3J-2 -- H H CH.sub.2 C(CH.sub.3)CH.sub.2 -- -- OCH.sub.3 CH.sub.3J-3 -- H H H -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H H -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- CH.sub.3 OCH.sub.3 CH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- CH.sub.3 OCH.sub.3 CH.sub.3__________________________________________________________________________ * symbols -o and .sub.--m refer to ortho and meta to the sulfonylurea bridge respectively.
TABLE IIIb__________________________________________________________________________ ##STR82## R.sub.1 or m.p.W.sub.2 W.sub.1 J n R R.sub.1 ' R.sub.3 R.sub.5 R.sub.6 R.sub.7 X.sub.1 Y.sub.3 (.degree.C.)__________________________________________________________________________-- S J-5 0 H H H CH.sub.3 -- -- OCH.sub.3 CH.sub.3-- S J-5 1 H H H CH.sub.3 -- -- OCH.sub.3 CH.sub.3O S J-6 0 H H H -- -- -- OCH.sub.3 CH.sub.3O S J-6 1 H H H -- -- -- OCH.sub. 3 CH.sub.3-- S J-7 0 H H H CH.sub.3 -- -- OCH.sub.3 CH.sub.3-- S J-7 1 H H H CH.sub.3 -- -- OCH.sub.3 CH.sub.3-- S J-8 -- H H H CH.sub.3 -- -- OCH.sub.3 CH.sub.3-- S J-9 -- H H H CH.sub.3 -- -- OCH.sub.3 CH.sub.3O S J-10 -- H H H -- H CH.sub.3 OCH.sub.3 CH.sub.3O S J-10 -- H H H -- H CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3O S J-6 1 H H H -- -- -- OCH.sub.3 HO S J-6 1 H H H -- -- -- CH.sub.3 HO S J-6 1 H H H -- -- -- OCH.sub.2 CH.sub.3 HO S J-6 1 H H H -- -- -- OCF.sub.2 H HO S J-6 1 H H H -- -- -- CH.sub.3 CH.sub.3O S J-6 1 H H H -- -- -- OCH.sub.2 CH.sub.3 CH.sub.3O S J-6 1 H H H -- -- -- OCF.sub.2 H CH.sub.3__________________________________________________________________________
TABLE IIIc__________________________________________________________________________ ##STR83## m.p.J W.sub.2 m' n R R.sub.1 ' R.sub.4 R.sub.5 R.sub.6 X.sub.1 Y.sub.3 (.degree.C.)__________________________________________________________________________J-11 O -- 0 H H CH.sub.3 H H OCH.sub.3 CH.sub.3J-11 O -- 1 H H CH.sub.3 H H OCH.sub.3 CH.sub.3J-11 S -- 0 H H CH.sub.3 H H OCH.sub.3 CH.sub.3J-11 S -- 1 H H CH.sub.3 H H OCH.sub.3 CH.sub.3J-12 O 1 0 H H -- H H OCH.sub.3 CH.sub.3J-12 O 2 0 H H -- H H OCH.sub.3 CH.sub.3J-12 O 1 1 H H -- H H OCH.sub.3 CH.sub.3J-12 O 2 1 H H -- H H OCH.sub.3 CH.sub.3__________________________________________________________________________
TABLE IVa__________________________________________________________________________ ##STR84## R.sub.1 * or m.p.J n R R.sub.1 '* R.sub.2 R.sub.3 R.sub.4 X.sub.2 Y.sub.2 (.degree.C.)__________________________________________________________________________J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.2 CH.sub.3 OCH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.2 CF.sub.3 OCH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 OCH.sub.2 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 SCH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 SCH.sub.2 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 CH.sub.2 CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 0 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- CH.sub.3 OCH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 H H -- CH.sub.3 OCH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 0 H -o-CH.sub.2 CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2 H -- CH.sub.3 OCH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 1 H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 H -- CH.sub.3 OCH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- CH.sub.3 OCH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- -- CH.sub.3 OCH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- -- CH.sub.3 OCH.sub.3J-2 -- H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 -- -- CH.sub.3 OCH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- -- CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3 -- CH.sub.3 CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- CH.sub.3 CH.sub.3 OCH.sub.3__________________________________________________________________________ *-- symbols -o and .sub.--m refer to ortho and meta to sulfonylurea bridg respectively.
TABLE IVb__________________________________________________________________________ ##STR85## R.sub.1 or m.p.W.sub.2 W.sub.1 J n R R.sub.1 ' R.sub.3 R.sub.5 R.sub.6 R.sub.7 X.sub.2 Y.sub.2 (.degree.C.)__________________________________________________________________________-- S J-5 0 H H H CH.sub.3 -- -- CH.sub.3 OCH.sub.3-- S J-5 1 H H H CH.sub.3 -- -- CH.sub.3 OCH.sub.3O S J-6 0 H H H -- -- -- CH.sub.3 OCH.sub.3O S J-6 1 H H H -- -- -- CH.sub.3 OCH.sub. 3-- S J-7 0 H H H CH.sub.3 -- -- CH.sub.3 OCH.sub.3-- S J-7 1 H H H CH.sub.3 -- -- CH.sub.3 OCH.sub.3-- S J-8 -- H H H CH.sub.3 -- -- CH.sub.3 OCH.sub.3-- S J-9 -- H H H CH.sub.3 -- -- CH.sub.3 OCH.sub.3O S J-10 -- H H H -- H CH.sub.3 CH.sub.3 OCH.sub.3O S J-10 -- H H H -- H CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3O S J-6 1 H H H -- -- -- CH.sub.3 OCH.sub.2 CH.sub.3O S J-6 1 H H H -- -- -- CH.sub.3 SCH.sub.3O S J-6 1 H H H -- -- -- CH.sub.3 SCH.sub.2 CH.sub.3O S J-6 1 H H H -- -- -- CH.sub.3 CH.sub.3O S J-6 1 H H H -- -- -- CH.sub.3 CH.sub.2 CH.sub.3O S J-6 1 H H H -- -- -- CH.sub.2 CH.sub.3 OCH.sub.3O S J-6 1 H H H -- -- -- CH.sub.2 CF.sub.3 OCH.sub.3__________________________________________________________________________
TABLE IVc__________________________________________________________________________ ##STR86## m.p.J W.sub.2 m' n R R.sub.1 ' R.sub.4 R.sub.5 R.sub.6 X.sub.2 Y.sub.2 (.degree.C.)__________________________________________________________________________J-11 O -- 0 H H CH.sub.3 H H CH.sub.3 OCH.sub.3J-11 O -- 1 H H CH.sub.3 H H CH.sub.3 OCH.sub.3J-11 S -- 0 H H CH.sub.3 H H CH.sub.3 OCH.sub.3J-11 S -- 1 H H CH.sub.3 H H CH.sub.3 OCH.sub.3J-12 O 1 0 H H -- H H CH.sub.3 OCH.sub.3J-12 O 1 1 H H -- H H CH.sub.3 OCH.sub.3J-12 O 2 0 H H -- H H CH.sub.3 OCH.sub.3J-12 O 2 1 H H -- H H CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE Va__________________________________________________________________________ ##STR87##J n R R.sub.1 or R'.sub.1 R.sub.2 R.sub.3 R.sub.4 X.sub.3 m.p. (.degree.C.)__________________________________________________________________________J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- CH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3J-1 0 H H CH.sub.2 CH.sub.2 CH.sub.2 Cl H -- OCH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 OCH.sub.3 H -- OCH.sub.3J-1 1 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H -- OCH.sub.3J-1 1 H H CH.sub.2 CH.sub. 2 CH.sub.2 Cl H -- OCH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- -- OCH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- -- OCH.sub.3J-2 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- -- OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OHC.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.3 -- CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3J-3 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 OCH.sub.3 -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 Cl -- CH.sub.3 OCH.sub.3J-4 -- H H H -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.3 -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 -- CH.sub.3 OCH.sub.3J-4 -- H H CH.sub.2 CH(CH.sub.3).sub.2 -- CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE Vb__________________________________________________________________________ ##STR88##W.sub.2 W.sub.1 J n R R.sub.1 or R.sub.1 ' R.sub.3 R.sub.5 R.sub.6 R.sub.7 X.sub.3 m.p. (.degree.C.)__________________________________________________________________________-- S J-5 0 H H H CH.sub.3 -- -- CH.sub.3-- S J-5 0 H H H CH.sub.3 -- -- OCH.sub.3-- S J-5 1 H H H CH.sub.3 -- -- CH.sub.3-- S J-5 1 H H H CH.sub.3 -- -- OCH.sub.3O S J-6 0 H H H -- -- -- CH.sub.3O S J-6 0 H H H -- -- -- OCH.sub. 3O S J-6 1 H H H -- -- -- CH.sub.3O S J-6 1 H H H -- -- -- OCH.sub.3-- S J-7 0 H H H CH.sub.3 -- -- CH.sub.3-- S J-7 0 H H H CH.sub.3 -- -- OCH.sub.3-- S J-7 1 H H H CH.sub.3 -- -- CH.sub.3-- S J-7 1 H H H CH.sub.3 -- -- OCH.sub.3-- S J-8 -- H H -- CH.sub.3 -- -- CH.sub.3-- S J-8 -- H H -- CH.sub.3 -- -- OCH.sub.3-- S J-9 -- H H -- CH.sub.3 -- -- CH.sub.3-- S J-9 -- H H -- CH.sub.3 -- -- OCH.sub.3O S J-10 -- H H -- -- H CH.sub.3 CH.sub.3O S J-6 -- H H -- -- H CH.sub.3 OCH.sub.3O S J-10 -- H H -- -- H CH.sub.2 CH.sub.3 CH.sub.3O S J-10 -- H H -- -- H CH.sub.2 CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE Vc______________________________________ ##STR89##J W.sub.2 m' n R R'.sub.1 R.sub.4 R.sub.5 R.sub.6 X.sub.3 m.p.(.degree.C.)______________________________________J-11 O -- 0 H H CH.sub.3 H H OCH.sub.3J-11 O -- 1 H H CH.sub.3 H H OCH.sub.3J-11 S -- 0 H H CH.sub.3 H H OCH.sub.3J-11 S -- 1 H H CH.sub.3 H H OCH.sub.3J-12 O 1 0 H H -- H H OCH.sub.3J-12 O 1 1 H H -- H H OCH.sub.3J-12 O 2 0 H H -- H H OCH.sub.3J-12 O 2 1 H H -- H H 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 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
TABLE VI______________________________________ Active Weight Percent* Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 5-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 1-95 5-99 0-15High Strength 90-99 0-10 0-2Compositions______________________________________
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff.
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 10
Wettable Powder
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 50%aminocarbonyl]-2-(2-methoxyethyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxidesodium 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 11
Granule
______________________________________Wettab1e Powder of Example 10 5%attapulgite granules 95%(U.S.S. 20-40 mesh; 0.84-0.42 mm)______________________________________
A slurry of wettable powder containing .apprxeq.25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
EXAMPLE 12
Extruded Pellet
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 25%aminocarbonyl]-2-(2-methoxyethyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxideanhydrous 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 13
Low Strength Granule
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 1%aminocarbonyl]-2-(3-methylbutyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxideN,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 14
Aqueous Suspension
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 40%aminocarbonyl]-2-(2-methoxyethyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxidepolyacrylic 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 15
Oil Suspension
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 35%aminocarbonyl]-2-(3-methylbutyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxideblend of polyalcohol 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 16
Granule
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 80%aminocarbonyl]-2-(2-methoxyethyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxidewetting 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
______________________________________ 2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 99%aminocarbonyl]-2-(2-methoxyethyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxidesilica 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
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 90%aminocarbonyl]-2-(3-methylbutyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxidedioctyl 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
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 40%aminocarbonyl]-2-(3-methylbutyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxidesodium ligninsulfonate 20%montmorillonite clay 40%______________________________________
The ingredients 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
Dust
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 10%aminocarbonyl]-2-(3-methylbutyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxideattapulgite 10%talc 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 talc until homogeneous.
EXAMPLE 21
Solution
______________________________________2,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl) 30%aminocarbonyl]-2-(3-methylbutyl)-1,2-benziso-thiazole-7-sulfonamide, 1,1-dioxidedimethylformamide 70%______________________________________
The ingredients are combined and stirred to produce a solution, which can be used for low volume applications.
Solutions of compounds of Formula I with J=J-5 to J-10 should be avoided due to the instability of the compounds when dissolved.
Utility
The compounds of the present invention are active herbicides. They 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, oil-well sites, drive-in theaters, around billboards, highway and railroad structures. Alternatively, the subject compounds are useful to modify plant growth. Certain of the compounds can be used to control weeds in crops such as wheat. The related compounds where J is J.sub.1, n is O, R.sub.1 =R.sub.3 =H and R.sub.2 is isobutyl show excellent control of wild oats both pre- and postemergence and are also useful for preemergence and postemergence control of grassy weeds in broadlead crops such as cotton and soybeans.
The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foilage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 5 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required.
The compounds of the invention may be used in combination with any other commercial herbicide; examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.
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), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, sugarbeet, rice, wheat and purple nutsedge (Cyperus rotundus) tubers, and in certain cases, cotton were planted and treated pre-emergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species, along with cotton and bush bean, were treated post-emergence with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 19 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:
C=chlorosis or necrosis;
E=emergence inhibition;
G=growth retardation;
H=formative effects;
L=lodging;
U=unusual pigmentation;
X=axiallary stimulation; and
6Y=abscised buds or flowers.
The data show that most of the compounds tested are highly active herbicides with growth modifying properties and that some of the compounds tested provide selective weed control in crops such as wheat, cotton and soybeans. It will be noted that all compounds were tested at the low rate of 50 g/ha. It is expected that compounds such as 10, 17, 19, 23, 25, 28, 34 and 35 will show improved activity at higher rates. ##STR90##
TABLE A Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 RATE G/HA 50 50 50 50 50 50 50 50 50 50 50 50 TYPE TEST POST COTTON 2C 3C 4C 9C 0 4C 4C 1C 4C 0 4C 2G 4G 8H 8G 7G 9G 6G 9H SORGHUM 3C 2C 5C 9C 3C 5C 4C 2C 3C 0 3C 4C 9G 9H 9H 7H 9H 9H 6H 9G 9G 9H CORN 2C 2C 3C 9C 2C 5C 5C 3C 3C 0 2U 4C 8H 9G 9G 2H 9H 9G 8H 9H 9G 9H SOYBEAN 2C 4C 5C 9C 0 4C 4C 0 3H 0 5C 5C 7H 9G 8G 8G 9G 9G WHEAT 5G 5G 2G 9C 0 2G 2G 0 0 0 6C 0 9G WILDOATS 4G 2C 2C 9C 2C 4C 4C 0 0 0 9C 3C 9G 5G 4G 7G 8G 8G RICE 3C 5C 9C 9C 2C 9C 9G 6G 4C 0 9C 5C 9G 9G 4G 9G 9G BARNYARDGRASS 2C 10C 5C 9C 3C 5C 6C 0 9C 0 10C 3C 9H 9H 8H 9H 9G 8H CRABGRASS 2G 5c 2C 10C 4G 6G 5C 0 3C 0 9C 2G 9G 7G 9G 6G MORNINGGLORY 2C 3C 9C 10C 1C 3C 10C 2C 3C 2G 5C 5C 3H 9G 2G 8G 3H 7H 8H 9H COCKLEBUR 3C 2C 3C 9C 0 2C 3C 2C 2C 0 4C 3C 5G 5H 8H 8G 8G 5H 8H 6H SICKLEPOD 3C 2G 5C 9C 1C 5C 9C 0 1C 0 3C 5C 5G 9G 9G 3H 9H NUTSEDGE 2G 8G 4C 9C 0 8G 4C 3G 2C 0 2C 2C 9G 9G 5G 5G SUGARBEETS 2C 9C 3C 10C 3G 2C 4C 2C 2C 0 5C 0 8G 7G 3G 9G 9G TYPE TEST PRE COTTON 0 2C 8G 2C 0 2G 8G 0 2G 0 5G 2G 8G 9G SORGHUM 0 4C 9G 10H 4G 4C 3C 2C 3C 0 3C 3C 9H 9G 9G 4G 9H 8G 9G CORN 0 4C 4U 5C 2C 2C 2C 2C 2C 0 2C 2C 9G 9H 9H 5G 7H 9G 7G 9G 9G 8G SOYBEAN 1C 4C 3C 4C 0 2C 3C 1C 2C 0 3C 2C 7G 7G 9H 5G 8G 7G 4G WHEAT 0 9C 0 10H 0 0 0 0 3G 0 0 0 WILDOATS 0 9C 2C 9C 2C 2C 9H 3G 3G 0 6C 4C 7G 5G 8H 9G 9G RICE 1C 10E 10E 10E 3c 10E 10E 8H 10E 0 9H 10E 8G 9H BARNYARDGRASS 0 4C 3C 9H 0 4H 9H 1C 3C 0 5C 4C 9H 9G 8H 6G 6G CRABGRASS 0 5C 2C 6C 0 2C 2C 2G 3G 0 4C 2G 9G 5G 9G 8G 9G 9G MORNINGGLORY 3G 9G 9G 9C 2C 6G 9G 2C 2C 0 8G 2C 9G 8G COCKLEBUR 5G 9H 8H 8H 0 5G 5G 1H 3G 0 7H 6H SICKLEPOD 5G 2C 8G 9G 0 2G 2G 0 3G 0 2G 2C 8G 4G NUTSEDGE 0 10E 10E 10E 0 0 10E 0 9G 0 0 5G SUGARBEETS 0 9C 9G 9C 0 4G 3C 2C 3G 0 3C 0 9G 7G Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound 18 Compound 19 Compound 20 Compound 21 Compound 22 Compound 23 Compound 24 RATE G/HA 50 50 50 50 50 50 50 50 50 50 50 50 TYPE TEST POST COTTON 0 8H 9H 0 0 8H 0 3C 3C 3G 0 3C 8H 9G 8H SORGHUM 2G 5C 6C 0 0 4C 0 3C 3C 0 0 2G 9G 9G 9G 8H 7H CORN 2C 4C 10C 2C 0 2C 2C 3C 3C 2C 0 3C 9H 9H 4H 5G 8H 8H 9H 7H 9H SOYBEAN 3C 5C 5C 2H 0 3C 0 5C 4C 0 0 0 9G 9G 9G 9H 9G 9G WHEAT 7G 8G 7G 0 0 3G 0 2G 0 0 0 3G WILDOATS 7G 1C 5G 0 0 0 0 0 0 0 0 0 RICE 3C 5C 5C 5G 0 4C 0 6C 5C 2G 0 6C 9G 9G 9G 8G 9G 9G 9G BARNYARDGRASS 0 3C 4C 0 0 9C 0 2C 3C 0 0 3C 9H 9H 9H 9H 9H CRABGRASS 0 2C 3C 0 0 0 0 2G 3C 0 0 2G 5G 9G 9G MORNINGGLORY 3C 4C 10C 2C 0 4C 0 5c 9C 0 0 2C 7G 9G 8G 9G 7H COCKLEBUR 3C 4C 10C 2C 0 5G 0 2C 2C 0 0 3G 9H 9H 3H 7G 6H SICKLEPOD 3C 6C 9C 0 0 2C 0 3C 2C 0 0 0 5H 9G 7G 8G NUTSEDGE 0 2C 2C 0 0 0 0 2C 2C 0 0 5G 9G 9G 7G 8G SUGARBEETS 3H 9C 9C 2H 0 9C 0 3C 9C 3H 0 0 7H TYPE TEST PRE COTTON 0 3G 8G 0 0 0 0 0 0 0 0 0 SORGHUM 0 3C 4C 6G 0 6C 0 0 2G 0 0 3C 8G 9G 9H 9G CORN 2C 3C 3C 4G 0 3C 0 0 2C 0 0 2C 5G 9G 9G 9H 8G 7G SOYBEAN 1C 6H 3C 1C 0 1C 0 0 2C 0 0 0 7H 3G 7G WHEAT 0 8G 4C 5G 0 6G 0 0 0 0 0 0 9G WILDOATS 0 3C 4C 0 0 6G 0 0 0 0 0 0 8G 8G RICE 2C 10E 10E 9G 0 10E 0 0 8G 0 0 9H 9H BARNYARDGRASS 0 3C 5C 0 0 3C 0 0 2H 0 0 0 7H 9H 7H CRABGRASS 0 2C 2C 0 0 1C 0 0 0 0 0 0 8G 7G MORNINGGLORY 0 8G 8H 0 0 5G 0 0 9G 0 0 2G COCKLEBUR 7G 9H 9H 0 1H 9H 0 0 4G 0 -- 0 SICKLEPOD 0 2G 7G 0 0 0 0 0 0 0 0 0 NUTSEDGE 0 8G 10E 0 0 10E 0 0 0 0 0 0 SUGARBEETS 8H 5C 5C 7G 3H 4C 0 0 8G 0 0 0 9G 9G 9G Compound 25 Compound 26 Compound 27 Compound 28 Compound 29 Compound 30 Compound 31 Compound 32 Compound 33 Compound 34 Compound 35 Compound 36 RATE G/HA 50 50 50 50 50 50 50 50 50 50 50 50 TYPE TEST POST COTTON 0 2C 0 0 5C 1C 3C 4C 2C 0 0 0 4G 9G 8H 9G 5G SORGHUM 0 3C 3C 0 5C 2G 4C 9C 5C 0 0 4C 8H 8H 9G 9H 9H 9H CORN 0 3C 3C 0 10C 2C 5C 10C 9C 0 0 2C 8H 7H 7H 9G 9H SOYBEAN 0 0 1C0 4C 2C 5C 4C 1H 0 0 2C 9G 2H 9G 9G 4H WHEAT 0 0 0 0 9C 5G 8G 6C 1C 0 0 3C 9G 2G 9G WILDOATS 0 1C 0 0 9C 2C 5C 6C 3C 0 0 9C 4G 9G 9G 7G RICE 0 3C 3C 0 5C 1C 5C 9C 5C 0 0 5C 9G 6G 9G 9G 9G 9G BARNYARDGRASS 0 3C 3C 0 10C 2G 5C 10C 10C 0 0 9C 9H 5H 9H CRABGRASS 0 1C 0 0 9C 0 2C 9C 9C 0 0 3C 8G 8H MORNINGGLORY 0 2C 3G 0 10C 0 3C 10C 2C 0 0 3H 5H 7H 3H COCKLEBUR 0 0 0 1H 10C 0 3C 5C 3G 0 0 3G 8H 9H SICKLEPOD -- -- -- -- -- -- -- -- -- -- -- -- NUTSEDGE 0 2C 0 0 9C 0 2C 4C 0 0 0 0 5G 9G 9G SUGARBEETS 0 0 0 0 10C 0 3C 10C 3C 0 0 3C 7H 7G 3H TYPE TEST PRE COTTON 0 0 0 0 2 C 0 2G 7G 0 0 0 0 9G SORGHUM 0 3C 0 0 9G 0 2C 9H 3C 0 0 2C 9H 7H 9H CORN 0 3C 2G 0 9G 0 2C 4C 2C 0 0 2G 8G 7H 9G 8H SOYBEAN 0 1C 0 0 3C 0 7G 4C 2C 0 0 0 8H 7G 2G WHEAT 0 0 0 0 2C 0 2G 9C 2G 0 0 5G 8G WILDOATS 0 0 0 0 2C 0 2C 9C 2C 0 0 7G 8G 7G 5G RICE 0 10E 0 0 9H 0 2C 9H 3C 0 0 0 6G 8H BARNYARDGRASS 0 3C 0 0 2C 0 0 3C 3C 0 0 2G 9H 5G 5H 8H CRABGRASS 0 3G 0 0 2C 0 5G 3C 2C 0 0 5G 7G 9G 4G MORNINGGLORY 0 2C 0 0 8G 0 3C 9C 3C 0 0 0 6H 6G 5G COCKLEBUR -- 5G 0 0 5H 0 9H 8H 0 0 0 0 SICKLEPOD -- -- -- -- -- -- -- -- -- -- -- -- NUTSEDGE 0 5G 0 0 10E 0 0 9G 0 0 0 0 SUGARBEETS 0 2H 0 0 4C 0 2C 4C 5H 0 0 0 9G 5G 9G 5H Compound 37 Compound 38 Compound 39 Compound 40 Compound 41 Compound 42 Compound 43 Compound 44 Compound 45 Compound 46 Compound 47 Compound 48 RATE G/HA 50 50 50 50 50 50 50 50 50 50 50 50 TYPE TEST POST COTTON 5C 5C 4C 0 0 10C 0 3C 5C 0 0 0 9H 9G 8H 8H 9G SORGHUM 9C 10C 9C 4C 4G 9C 2C 9C 9C 10C 9H 2C 8H 4H 5H CORN 10C 10C 10C 6C 3C 10C 3C 10C 10C 10C 3C 3C 9H 8H 8H 9H 7H SOYBEAN 5C 9C 3H 1C 3G 9C 6G 3C 10C 7G 1H 0 9G 6G 3G 8H 5X WHEAT 9C 9C 4C 5C 2C 10C 6C 3C 9C 3G 2C 2G 9G 8G 9G 9G 6G WILDOATS 10C 9C 2C 4C 3C 10C 10C 10C 10C 6C 9C 5C 9G 9G 8G 9H 9G RICE 9C 9C 9C 4C 3C 9C 9C 9C 9C 9C 4C 8G 9G 9G BARNYARDGRASS 10C 9C 10C 4C 3C 10C 4C 9C 9C 9C 3C 0 8H 5H 9H CRABGRASS 9C 10C 7C 0 0 10C 3C 9C 10C 9C 0 0 9H 8G MORNINGGLORY 10C 10C 2C 0 0 10C 0 4C 10C 2C 0 0 7G 8H 5H COCKLEBUR 5C 9C 4C 2G 0 10C 0 4C 10C 2C 2G 1H 9H 8H 9H 7G SICKLEPOD -- -- -- -- -- -- -- -- -- -- -- -- NUTSEDGE 4C 9C 2C 3G 0 10C 0 3C 9C 2C 0 0 9G 5G 8G 3G SUGARBEETS 10C 10C 5C 2C 0 10C 4H 3C 9C 4H 3H 0 9H 5H 8H TYPE TEST PRE COTTON 5G 8G 0 0 0 9G 0 5G 9G 0 0 0 SORGHUM 5C 5C 9C 2C 0 7C 4G 4C 9H 3C 0 0 9H 9H 3G 9H 9H 9H CORN 5C 10H 5C 2C 0 10E 3G 3C 9G 2C 2C 0 9H 9H 5G 9G 8G 4G SOYBEAN 3C 4C 3C 0 0 9H 0 2C 2C 0 0 0 7G 8H 4G 4H 7G WHEAT 7C 9C 6G 7G 0 9H 0 2G 8G 3G 0 0 9H WILDOATS 9C 10C 2C 3G 0 9C 2C 9C 9C 7G 2G 0 5G 6G RICE 5C 10H 5C 2C 0 10E 2C 10E 10E 10E 2G 0 9H 9H 3G 7G BARNYARDGR ASS 3C 9C 2C 1C 0 4C 1H 3C 4C 3C 2H 0 7H 8H 9H 9H 9H 9H CRABGRASS 10H 10H 3C 0 0 10C 0 4C 10C 3C 0 0 7G 9H 9G MORNINGGLORY 3C 5C 3C 2C 0 10C 0 3C 9G 3G 0 0 7H 9G 7H 4H 6H COCKLEBUR 9H 4C 2H -- 0 9H 0 -- 8H 2G 0 0 9H SICKLEPOD -- -- -- -- -- -- -- -- -- -- -- -- NUTSEDGE 10E 10E 4G 0 0 10E 0 3C 10E 10E 0 0 5G SUGARBEETS 6C 6C 2C 3H 0 10C 0 4C 5C 5G 0 0 9G 9G 5H 9H 9G Compound 49 Compound 50 Compound 51 Compound 52 Compound 53 Compound 54 RATE G/HA 50 50 50 50 50 50 TYPE TEST POST COTTON 4G 9H 9C 9H 0 0 SORGHUM 4C 6C 9C 9C 3C 2C 8H 9G 8H 3H CORN 5C 9C 10C 9C 3C 3C 9H 8H 9H SOYBEAN 2H 4C 4C 6H 0 0 5G 9G 9G WHEAT 4C 9C 5C 2C 2c 2G 9G 9G 6G 6G WILDOATS 5C 9C 9C 3C 2C 2C 9G 7G 5G 5G RICE 5C 9C 6C 9C 2C 9G 9G 9G 9G BARNYARDGRASS 3C 9C 9C 10C 6H 4H 6H CRABGRASS 5G 5C 10C 9C 0 0 9G MORNINGGLORY 3C 5C 10C 10C 0 0 8H 9G COCKLEBUR 4G 4C 10C 8H 1H 0 9H SICKLEPOD -- -- -- -- -- -- NUTSEDGE 2c 4C 9C 3C 0 0 8G 9G 8G SUGARBEETS 3C 10C 9C 10C 1H 0 7H TYPE TEST PRE COTTON 0 3G 9G 6G 0 0 SORGHUM 2G 4C 6C 9C 2G 0 9H 9H CORN 5G 9G 5C 3C 6G 2G 9H 9H SOYBEAN 0 3C 3C 2C 0 1C 7G 8G 5G WHEAT 7G 9G 6C 3C 5G 0 9H 7G WILDOATS 3C 9C 7C 3C 2G 2C 9G 9H 8G 3G RICE 8H 5C 10E 10E 3G 3G 9H BARNYARDGRASS 0 5C 7C 6C 0 0 9H 9H 9H CRABGRASS 0 5C 7C 3C 0 0 9G 9H 7G MORNINGGLORY 3C 9H 9C 8H 0 0 COCKLEBUR 0 -- 9H 5H 0 0 SICKLEPOD -- -- -- -- -- -- NUTSEDGE 0 9G 10E 3C 0 0 9H SUGARBEETS 0 9G 9C 5C 2G 4G 9G
TEST B
Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Fallsington slit loam soil. One pan was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Amena fatua), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides) annual bluegrass (Poa annua), green foxtail (Setaria viridis), rapeseed (Brassica napus), and Italian ryegrass (Lolium multiflorum). The other pan was planted with seeds of Russian thistle (Salsola kali), speedwell (Veronica persica), kochia (Kochia scoparia), shepherd's purse (Capsella bursa-pastoris), Matricaria inodora, black nightshade (Solanum nigrum), and wild buckwheat (Polygonum convolvulus). The above two pans were treated preemergence. At the same time two pans in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species.
The compounds applied were diluted with a nonphytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated. The recorded data are presented in Table B.
TABLE B__________________________________________________________________________TYPE RATE BAR- WILD- CHEAT- BLACK- BLUE- FOX- RYE- CIAB- RAPE-TEST G/HA WHEAT LEY OATS GRASS GRASS GRASS TAIL GRASS GRASS SEED__________________________________________________________________________ Compound 2POST 125 10C 10C 10C 9G 10C 10C 10C 10C 10CPRE 125 8G 9G 9G 10C 9G 8G 10C 10C 9GPOST 64 8G 10C 10C 8G 10C 10C 10C 10C 10CPRE 64 7G 7G 9G 9G 9G 9G 9G 8G 5GPOST 32 3G 10C 7C 7G 9G 10C 10C 7G 10CPRE 32 6G 6G 8G 8G 7G 7G 7G 7G 0POST 16 0 10C 10C 7G 9G 10C 10C 6G 9GPRE 16 4G 4G 6G 7G 4G 7G 2g 4G 0POST 8 0 9G 8G 0 3G 4G 9G 4G 9GPRE 8 0 2G 4G 3G 4G 4G 0 2G 0__________________________________________________________________________ MATRI- CARIATYPE RATE INO- SHEPARDS- NIGHT- SPEED- BUCK- SUGAR-TEST G/HA DORA GALIUM THISTLE PURSE KOCHIA SHADE WELL WHEAT BEETS__________________________________________________________________________ Compound 2POST 125 6G 10C 10C 9G 8G 10C 0 7G 9GPRE 125 8G 10C 0 9G 9G 8G 0 9G 10CPOST 64 5G 10C 10C 8G 8G 8G 0 7G 9GPRE 64 7G 9G 0 9G 6G 8G 0 9G 10CPOST 32 2G 7G 10C 9G 5G 6G 0 0 9GPRE 32 7G 7G 0 9G 0 7G 0 5G 9GPOST 16 0 5G 10C 9G 0 0 0 0 9GPRE 16 6G 6G 0 7G 0 5G 0 0 5GPOST 8 0 4G 7G 8g 0 0 0 0 3GPRE 8 3G 4G 0 6G 0 2G 0 0 4G__________________________________________________________________________TYPE RATE BAR- WILD- CHEAT- BLACK- BLUE- FOX- RYE- CIAB- RAPE-TEST G/HA WHEAT LEY OATS GRASS GRASS GRASS TAIL GRASS GRASS SEED__________________________________________________________________________ Compound 3POST 125 0 0 0 0 5G 3G 7G 0 10CPRE 125 0 0 0 0 0 0 0 0 0POST 64 0 0 0 0 4G 0 6G 0 8GPRE 64 0 0 0 0 0 0 0 0 0POST 32 0 0 0 0 0 0 0 0 7GPRE 32 0 0 0 0 0 0 0 0 0POST 16 0 0 0 0 0 0 0 0 4GPRE 16 0 0 0 0 0 0 0 0 0POST 8 0 0 0 0 0 0 0 0 2GPRE 8 0 0 0 0 0 0 0 0 0__________________________________________________________________________ MATRI- CARIATYPE RATE INO- SHEPARDS- NIGHT- SPEED- BUCK- SUGARTEST G/HA DORA GALIUM THISTLE PURSE KOCHIA SHADE WELL WHEAT BEETS__________________________________________________________________________ Compound 3POST 125 5G 10C 10C 7G 10C 0 0 6G 0PRE 125 7G 8G 4G 9G 7G 8G 0 0 4GPOST 64 0 6G 9G 7G 3G 0 0 0 0PRE 64 7G 2G 4G 6G 7G 6G 0 0 0POST 32 0 4G 8G 6G 0 0 0 0 0PRE 32 6G 2G 3G 4G 5G 4G 0 0 0POST 16 0 0 7G 6G 0 0 0 0 0PRE 16 4G 0 0 3G 0 0 0 0 0POST 8 0 0 3G 5G 0 0 0 0 0PRE 8 0 0 0 0 0 0 0 0 0__________________________________________________________________________

Number	Name	Date	Kind
4546197	Kunz	Oct 1985
4744816	Bolinski et al.	May 1988

	Number	Date
Parent	716351	Mar 1985
Parent	663555	Oct 1984
Parent	607989	May 1984

Phenyl-substituted sulfonamides

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