HERBICIDAL ACETALS AND KETALS

ACETALS ET CETALS HERBICIDES

English Abstract

Title
HERBICIDAL ACETALS AND KETALS
Abstract of the Disclosure
This invention relates to novel furan- and
thiophenesulfonamides such as 3-(1,3-dioxolan-2-yl)-N-
[(4-methoxy-6-methyl-1,3-5-triazin-2-yl)aminocarbonyl]-
2-thiophenesulfonamide and N-[(4,6-dimethoxypyrimidin-
2-yl)aminocarbonyl]-3-(1,3-dioxolan-2-yl)-2-thiophene-
sulfonamide which are highly active pre-emergent and/or
post-emergent herbicides. More specifically, the
herbicides are of the formula:
<IMG>
I
wherein
Q is <IMG>
Q-1 Q-2 Q-3
<IMG>
Q-4 Q-5 Q-6

<IMG>, <IMG>, <IMG> or
O-7 O-8 O-9
<IMG>
O-10
R is H or CH3:
R1 is <IMG>, <IMG> or <IMG>
E is CH2 or a single bond:
R2 is H, C1-C2 alkyl or C1:
R3 is H, C1-C3 alkyl or C1-C3 alkoxy:
R4 is R5 are independently C1-C2 alkyl:
R6 and R7 are independently H or C1-C2 alkyl:
W is O or S:
W1 is O or S:
Q1 and Q2 are independently O, S or NCH3:
A is <IMG> , <IMG> , <IMG>
A-1 A-2 A-3
<IMG> , <IMG> , <IMG> or
A-4 A-5 A-6

<IMG>
A-7
X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo-
alkoxy. C1-C4 haloalkyl . C1-C4 haloalkylthio.
C1-C4 alkylthio, halogen, C2-C5 alkoxyalkoxy,
amino, C1-C3 alkylamino or di(C1-C3)alkylamino:
Y is H. C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo-
alkoxy, C1-C4 haloalkylthio, C1-C4 alkylthio,
halogen. C2-C5 alkoxyalkyl, C2-C5 alkoxyalkoxy.
amino, C1-C3 alkylamino, di(C1-C3)alkylamino,
C3-C4, alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkyl-
sulfinylalkyl, C1-C4 haloalkyl, C2-C5 alkyl-
sulfonylalkyl. C3-C5 cycloalkyl. C2-C4 alkynyl,
C2-C5 alkylthioallsyl. C(O)R8,
<IMG> , <IMG> , or
N(OCH3)CH3:
m is 2 or 3:
L1 and L2 are independently O or S:
R8 is H or CH3:
R9 and R10 are independently C1-C2 alkyl:
R11 is C1-C3 alkyl
R12 is H. F. C1, NO2. C1-C2 alkyl, C1-2 alkoxy
C1-C2 alkylthio, C1-C2 alkylsulfinyl, C1-C2 alkyl-
sulfonyl. di(C1-C2)alkylsulfamoyl or CO2(C1-C2
alkyl):
R13 is H, C1-C2 alkyl, C1-C2 alkoxy, C1, F or NO2;
R14 is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo-

alkyl, C1-C3 haloalkoxy, C1, Br, F, NO2,
di(C1-C3)alkylsulfamoyl, C1-C3 alkylthio, C1-C3
alkylsulfinyl, C1-C3 alkylsulfonyl, amino, C1-C3
alkylamino, di(C1-C3)alkylamino, CH2OCH3,
CH2SCH3 or CH2CN.
Z is CH or N;
Y1 is O or CH2;
X1 is CH3, OCH3, OC2H5 or OCF2H; and
Y2 is H or CH3;
X2 is CH3, C2H5 or CH2CF3;
Y3 is OCH3, OC2H5, SCH3, SC2H5, OCF2H, SCF2H,
CH3 or C2M5;
X3 is CH3 or OCH3;
Y4 is CH3, OCH3, OC2H5 or C1; and
X4 is CH3, OCH3, OC2H5, CH2OCH3 or C1;
and their agriculturally suitable salts;
provided that
a) when X is C1, F, Br, or I, then Z is CH and Y is
OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H;
b) when Y is cyclopropyl, X is other than C1, F, Br
or I;
c) when R3 is C1-C3 alkoxy, then Q1 and Q2 are
oxygen;
d) when R3 is H or C1-C3 alkyl, then Q is Q-1
through Q-9;
e) when X or Y is OCF2H, then Z is CH;
f) when the total number of carbon atoms of X and
Y is greater than four, then the combined number
of carbons of the substituents on Q is less than
or equal to ten;
g) when W is S, then A is A-1, R is H, and Y is
CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3,
OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2

or <IMG>;
h) when A is A-7 and Z is N, then R3 is C1-C3
alkoxy;
i) when E is CH2, then R14 is H, CH3, OCH3, C1 or
NO2 and is not in the 4-position.

Claims

BA-8596-A-l
WHAT IS CLAIMED IS:
1. A compound of the formula
<IMG>
I
wherein
Q is <IMG>
Q-1 Q-2 Q-3
<IMG>
Q-4 Q-5 Q-6
<IMG>
Q-7 Q-8 Q-9
or <IMG>
Q-10
122

R is H or CH3;
R1 is <IMG> or <IMG>;
E is CH2 or a single bond;
R2 is H, C1-C2 alkyl or C1:
R3 is H, C1-C3 alkyl or C1-C3 alkoxy;
R4 and R5 are independently C1-C2 alkyl;
R6 and R7 are independently H or C1-C2 alkyl:
W is O or S:
W1 is O or S;
Q1 and Q2 are independently O, S or NCH3;
A is <IMG>
A-1 A-2 A-3
<IMG> or
A-4 A-5 A-6
<IMG>
A-7
123

X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo-
alkoxy, C1-C4 haloalkyl, C1-C4 haloalkylthio,
C1-C4 alkylthio, halogen. C2-C5 alkoxyalkoxy,
amino, C1-C3 alkylamino or di(C1-C3)alkylamino;
Y is H, C1-C4 alkyl, C1-C alkoxy, C1-C4 halo-
alkoxy, C1-C4 haloalkylthio, C1-C4 alkylthio,
halogen, C2-C5 alkoxyalkyl, C2-C5 alkoxyalkoxy,
amino, C1-C3 alkylamino, di(C1-C3)alkylamino,
C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkyl-
sulfinylalkyl, C1-C4 haloalkyl, C2-C5 alkyl-
sulfonylalkyl, C3-C5 cycloalkyl, C2-C4 alkynyl,
C2-C5 alkylthioalkyl, C(O)R8,
<IMG> or
N(OCH3)CH3;
m is 2 or 3;
L1 and L2 are independently O or S;
R8 is H or CH3;
R9 and R10 are independently C1-C2 alkyl;
R11 is C1-C3 alkyl;
R12 is H, F, C1, NO2, C1-C2 alkyl, C1-C2 alkoxy,
C1-C2 alkylthio, C1-C2 alkylsulfinyl, C1-C2
alkylsulfonyl, di(C1-C2)alkylsulfamoyl or
CO2(C1-C2 alkyl)
R13 is H, C1-C2 alkyl, C1-C2 alkoxy, C1, F or NO2;
R14 is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo-
alkyl, C1-C3 haloalkoxy, C1, Br, F, NO2,
di(C1-C3)alkylsulfamoyl, C1-C3 alkylthio, C1-C3
alkylsulfinyl, C1-C3 alkylsulfonyl, amino, C1-C3
alkylamino, di(C1-C3)alkylamino, CH2OCH3,
CH2SCH3 or CH2CN.
Z is CH or N;
Y1 is O or CH2;
124

X1 is CH3, OCH3, OC2H5 or OCF2H; and
Y2 is H or CH3;
X2 is CH3, C2H5 or CH2CF3;
Y3 is OCH3, OC2H5, SCH3, SC2H5, OCF2H, SCF2H,
CH3 or C2H5;
X3 is CH3 or OCH3;
Y4 is CH3, OCH3, OC2H5 or C1; and
X4 is CH3, OCH3, OC2H5, CH2OCH3 or C1;
and their agriculturally suitable salts:
provided that
a) when X is C1, F, Br or I, then Z is CH and Y is
OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H;
b) when Y is cyclopropyl, X is other than C1, F, Br
or I:
c) when R3 is C1-C3 alkoxy, then Q1 and Q2 are
oxygen;
d) when R3 is H or C1-C3 alkyl, then Q is Q-1
through Q-9;
e) when X or Y is OCF2H, then Z is CH;
f) when the total number of carbon atoms of X and
Y is greater than four, then the combined number
of carbons of the substituents on Q is less than
or equal to ten;
g) when W is S, then A is A-1, R is H, and Y is
CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3,
OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2
or <IMG>;
h) when A is A-7 and Z is N, then R3 is C1-C3
alkoxy;
i) when E is CH2, then R14 is H, CH3, OCH3, C1 or
NO2 and is not in the 4-position; and
j) when W1 is S, then Q is other than Q-1.
125

2. A compound of Claim 1 where R3 is H or
C1-C3 alkyl.
3. A compound of Claim 1 where R3 is C1-C3
alkoxy.
4. A compound of Claim 2 where W is O; R is H;
X is CH3, OCH3, OC2H5, C1, F, Br, I, OCF2H, CH2F,
OCH2CH2F, OCH2CHF2, OCH2CF3 or CF3; and Y is H,
C1-C3 alkyl, OCH3, OC2H5, CH2OCH3, NHCH3,
N(OCH3)CH3, N(CH3)2, CF3, SCH3, OCH2CH=CH2,
OCH2C?CH, OCH2CH2OCH3, CH2SCH3, CH2OC2H5,
<IMG>, OCF2H,
SCF2H, cyclopropyl, C?CH or C?CCH3.
5. A compound of Claim 4 where Q1 and Q2 are
identical and are O or S. R12 is H, C1-C2 alkyl or C1
and Rl3 iS H.
6. A compound of Claim 5 where A is A-1; Y is
CH3, OCH3, OC2H5, CH2OCH3, C2H5, NHCH3,
CH2OC2H5, OCF2H, OCH2CH2OCH3, cyclopropyl, C?CH or
CH(OCH3)2; and X is CH3, OCH3, C1, OC2H5, OCF2H or
OCH2CF3.
7. A compound of Claim 6 where Q1 and Q2 are O.
8. A compound of Claim 6 where Q1 and Q2 are S.
9. A compound of Claim 6 where Q is Q-1.
10. A compound of Claim 6 where Q is Q-2.
11. A compound of Claim 6 where Q is Q-3.
12. A compound of Claim 6 where Q is Q-4.
13. A compound of Claim 6 where Q is Q-5.
14. A compound of Claim 6 where Q is Q-6.
15. A compound of Claim 6 where Q is Q-7.
16. A compound of Claim 6 where Q is Q-8.
17. A compound of Claim 6 where Q is Q-9.
126

18. A compound of Claim 3 where W is O; R is H;
X is CH3, OCH3, OC2H5, C1, F, Br, I, OCF2H, CH2F,
OCH2CH2F, OCH2CHF2, OCH2CF3 or CF3; and Y is
H, C1-C3 alkyl, OCH3, OC2H5, CH2OCH3, NHCH3,
N(OCH3)CH3, N(CH3)2, CF3, SCH3, OCH2CH=CH2,
OCH2C?CH, OCH2CH2OCH3, CH2SCH3, CH2OC2H5,
<IMG>, OCF2H,
SCF2H, cyclopropyl, C?CH or C?CCH3.
19. A compound of Claim 18 where E is a single
bond; R12 is H, C1-C2 alkyl or C1; R13 is H; and
R14 is H, F, C1, Br, C1-C2 alkyl, C1-C2 alkoxy
or C1-C2 alkylthio and is not para to the sulfonylurea
bridge.
20. A compound of Claim 19 where A is A-1; Y is
CH3, OCH3, OC2H5, CH2OCH3, C2H5, NHCH3,
CH2OC2H5, OCF2H, OCH2CH2OCH3, cyclopropyl,
C?CH or CH(OCH3)2; and X is CH3, OCH3, C1,
OC2H5, OCF2H or OCH2CF3.
21. A compound of Claim 20 where Q is Q-1.
22. A compound of Claim 20 where Q is Q-2.
23. A compound of Claim 20 where Q is Q-3.
24. A compound of Claim 20 where Q is Q-4.
25. A compound of Claim 20 where Q is Q-5.
26. A compound of Claim 20 where Q is Q-6.
27. A compound of Claim 20 where Q is Q-7.
28. A compound of Claim 20 where Q is Q-6.
29. A compound of Claim 20 where Q is Q-9.
30. A compound of Claim 20 where Q is Q-10.
31. A compound of Claim 1 which is 3-(1,3-
dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-
2-yl)aminocarbonyl]-2-thiophenesulfonamide.
32. A compound of Claim 1 which is N-[(4,6-
dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1,3-dioxolan-
2-yl)-2-thiophenesulfonamide.
127

33. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 1.
34. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 2.
35. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 3.
36. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an affective amount of a
compound of claim 4.
37. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 5.
38. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 6.
39. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 18.
40. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 19.
41. A method for controlling the growth of
undesired vegetation which comprises applying to the
locus to be protected an effective amount of a
compound of claim 20.
128

Description

~S~3
BA-~596-A
H~RBICIDAL AC~TALS ~ND KE~ALS
a~qround_of th~ Invention
The present in~ent~o~ relate6 to a ~ovel cla~
of furan- and ~hiophene6ul~0namide co~pound~ and ~e~r
u6e as pre-emergent and po~t-emergent herbicides and
as plant growth ~egula~ts.
U.S. Patent ~os. 4,169,719 and 4,127,405
disclose he~bicidal benze~e-. furan- ana
thiophene6ulfonamides of general formula
X
- W N_~
RlS02NHCNH 4 O Z
Y
- ~5
where
Rl may be a~ optionally 6ub6tituted benzene or
a furan or thiophene substituted with H, Cl,
Br or CH3.
U.S. Patent No. ~,398,93~ di~clo~e6 he~bicidal
thiophenesulfonamide6 of for~ula
R o N__~
2s ~ "
~here
R i6 C1-~4 alkyl, C3 alke~yl, 0CH3,
N02. Cl, Br, S02NRlR~ or S02N~OCH3~C~3.
Europea~ Patent Application (~P-~ No. 30.142,
published June 10, 1981 discloses herblcidal furan- and
thiophene~ul~ona~ides of ~or~ula

~259~
~ W~ ~ 2
where
is 0 or S:
A is Ct0)QR or C(YT)R ; and
A~ i6 H, Cl, Br, Cl-C4 alkyl, OCH3.
N02 or CF3.
U.S~ Patent No. 4J370~480 teache6 herbicidal
benzene&ulfonamide6 of general ~or~ula
~ SO~NNCN
3 R5 N
where
ao R\O ~ R;~
; EP-A-64,804, published November 17, 1982, teaches
herbicidal ~uran- and thiophenesulfona~ide~ of genaral
f0r~ula
'~ Rl X
R~o2NHCN40<Z
Q R~ N
where
Rl is S(O)~R6; and
R2 ~s H, Cl, ~r or C~3;

~5~ 3
~ P-A-13.4BO di6clo~e6 hs~bic~d~l p~ridine-
6ulfonam~de6 of formula
R
R~!~S02NHCN~
R4 N
wher~
Rl is H. Cl, Br, F, Cl-C4 alkyl, Cl-C~
alkoxy. Cl-C~ alkyl~hio, N02 or C02R5: and
R2 i6 H, Cl, Br or CH3.
~P-A-35,893 discloses herbicidal pyridine-
sulfonamides of formula
O N
R2~S02NHCNH~
where
Rl is S(O)nR3; and
R2 is H. Cl, F, Br, CH3. OCH3, CF3, N02.
CN or NH2.
EP-A-97,122, published December 28, 1983,
di6closes herbicidal ~ulfonamide6 of formula
/ 1
S02NHCZNH4~e
3 YCHF~
where
X i6 O, S, NR4 or CR5=N; and
R2 i~ H, Cl-C3 alkyl, haloalkyl, alko~y,
alkyl~hio, alkylsulfonyl , haloge~, N02, CWR8,
$ZNR6R7 or CORg
EP-A-95,~25, publi~hed ~ecember 7, 1983, and
EP A-87,780, publi~hed September 7, 1~83, ~each
herbicidal pyrazole sulonylurea~.

~ZS~3
.. 3~
~P A-95,925 (publi~he~ D~ce~ber 7, lg83) ~nd
~P-A-87,780 (publi~hed Septe~ber 7, 19833 teach
herbicidal pyrazole sul~4nylureas.
EP-A-126,711 ~published November 28, 1984: Swis5
priority May 16, 1983) disclosed herbicidal sulfonylureas
of the formula
R4 ~ ''
wherein
X i6-0, S, -NR5, -f~N- -CH~CH- or an annelated
~5
. phenyl ring:
- Z i6 0 or S;
Q i~ halogen, Cl-C4 al~yl, cyano, etc.:
Rl i~ H, halogen, N02 or a group -f(OCl-C4 alkyl),
- R6
~t~.;
R6 i6, inter alia, H or Cl-C4 alkyl: and
Rz and R3 can be, ~ong oSher things, Cl-C4 alkyl
or Cl-C4 alkoYy.

~;~5~961~
Bummarlr of the Inventio~
Thi~ invention relates to novel compounds o~
Formula I. agriculturally suitable compo~itions co~-
taining them and their method-of-u6e as preemergent
and/or po6temergent her~icide6 or plant grow~h
regulant~.
QS02NHC~
R
I
wherein
~1 ~ R12
Q-l Q-2 Q=~
Rll R~
-4 Q-5 Q-6
3 0
Q-7 Q-8 Q=~

~L~59~i~L3
1~1 5~1:
Q-l~
R i6 H or CH3:
,QlP~4 ~ a6 or ~ ~ :
R\Q2R5 ~Q2 R7 ~Q2
i~ CH2 or a ~ingle bond:
R2 ~ 6 H~ Cl-C2 alkyl or Cl;
~3 i~ ~, Cl-C3 ~alkyl or Cl-C3 ælkoYy:
R~ and ~5 are independently Cl-C2 l~lkyl;
R6 and R7 are independently ~ ~r Cl-C2 alkyl;
~d i6 0 or ~;
O o~ S;
Ql and Q2 are independently 0, S or NCE~3;
a:L ~ a~
~ , ~( , ~B2~ r
~ a~ ~

96~3
4
A-7
~ i~ H, Cl-C4 alkyl, Cl-C~ alkoxy~ Cl-C4 halo-
alkoxy, Cl-C~ haloalkyl, Cl-C4 haloalkylt~io~
Cl-C4 alkylthio, ~aloqen, C2-C5 alko~yalkoxy,
amino, Cl-C3 al~ylamino or di~Cl-C3)alkylami~o;
Y i~ H C -C alkyl. C -C4 alkoxY. Cl-C~ halo-
alkoYy, Cl-C4 haloalkylthio, Cl-C~ alkyl~hio,
halogen, C2-C5 alkoYyalkyl, C2-C5 alkoxyalkoxy,
amino. Cl-C3 slkyla~ino, di(Cl-C3)alkylamino,
C3-C4 alkenyloxy. C3-C4 alkynylosy. C2-C5 alkyl-
6ulfinylalkyl, Cl-C4 haloalkyl, C2-C5 alkyl-
6ulfo~ylalkyl, C3-CS cycloalkyl, C2-C~ alkynyl,
C2-C5 alkylthioalkyl, C(O)R~,
-C 1 ' -C~L~ Z ~ \I3~ 3 r
N(QCH3)CH3:
~ i& 2 or 3;
Ll and L2 are i~dependently O or S:
R8 i6 % o~ C~3:
Rg and Rlo ~re independently Cl-C2 alkyl;
~ ~6 Cl-C3 alkyl:
~12 i~ H, F, Cl, No2, C~-Cz ~lkyl, Cl~C2 alkoxy,
Cl-C2 alkylthio, Cl-C? alkyl~ul~inylt Cl-C2 alkyl-
~ulfonyl, di(Cl-C2~alkyl~ulfamoyl ~ C02(Cl-C2
alkyl);
R i~ H C -C alkylJ Cl-C2 alkoxy, Cl, ~ or No~;

~5~ 3
R14 ~ H, Cl-C3 alkyl, Cl-C3 alkoxy, Cl-C3 halo
alkyl, Cl-C3 haloalkoxy, Cl, Br, F. N02,
diSCl-C3)alkyl~ulfamoyl~ Cl-C3 alkylthio, Cl-C~
alkyl~ulfinyl, Cl-C3 alkylsulfonyl, amino, Cl-C3
s alkylamino, di(Cl-C3)alkylamino, CH2OCH3,
CH2SCH3 or CH2CN.
Z iB CH or N;
Yl i6 O or CH2;
~1 i6 CH3, OCH3. OC2H5 or OCF2H: and
Y2 i8 H o~ CH3;
2 i8 CH3. C2H5 or CH2CF3;
Y i~ OcH3, OC2ff5~ SCH3, SC2H5, OCF2H, 2 3
or C2H5;
3 3 3;
Y~ is CH3. OCH3. OC2H5 or Cl; and
X4 is CH3. OCH3- 2 5~ H2 H3
and their agriculturally 6uitable ~alts;
pro~ided that
a) when X i6 Cl. F, Br or I, then Z i~ C~I and Y is
0CH3, 0C2H5, N(OCH3)CH3, NHCH~ N(CH3~2 or OCF2H;
b) when Y i8 ~yclopropyl, ~ is other than Cl, ~, Br
or I:
c) when R3 i6 Cl-C3 alkoxy, then Ql and Q2 are
oxygen;
d) when ~3 i6 H or Cl-C3 alkyl, then Q i~ Q-l
through Q-9;
e) when X or Y i~ OCF2~, then Z i~ CH:
f) when the total number of carbon a~om~ of X and
Y i8 grea~er than four, then ~he combined number
of carbon~ of the fiub~ti~uen~ o~ Q i5 le6~ than
or equal to ten;

9~i~3
g3 whe~ W i~ S, t~en A i~ A-l, R i8 H, and Y i~
3 3~ 0~2H5' CH20C~3~ C2H5, CP3, SCH
OCH2CH-CH2, OCEI2C_CH, OCH2CH2C)CH3, CH(OCH332
or C~ ~ :
h) when A i~ A-7 and Z i~ N, then R3 i6 Cl-C3
alkoxy;
i) when E i6 CH2, then R14 i~ H, CH3, OCH3, Cl or
N02 and i6 not in the 4-position.
In the above definitions, the term "alkyl~ u~ed
either alone or in compound words &uch as ~alkylthio~
or ~haloalkyl~, denote~ ~traight chain or branched
alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the
different butyl isomer6.
Alkoxy denote6 methoxy, ethoxy, n-propoxy, i60-
propoxy and the differen~ butoxy isomers.
Alkenyl denotes ~traight chain or branched
alkenes, e.g., l-propenyl, 2-propenyl, 3-propenyl and
the diEferent butenyl i~o~ers.
Alkynyl denote~ 6traight chain or branched
al~yne~, e.g., et~ynyl, 1-propynyl, 2-propynyl and
the dif~erent butynyl i~omer~. `
Cycloal~yl denote~ cyelopropyl, cyclobutyl and
Cyclope~tyl.
The term "halogen", either alone or in compound
word~ 6uch a~ "haloalkyl", denote6 ~luorine, chlor~ne,
bromine or iodine.
In terms such as C2-C5 alkoxyalkoxy, the
6pecified number of carbon atom~ i~ meant to define
the ~otal number of carbon ato~ in ~hat 6ubs~ituent
group. For example, C2-C5 alkoxyalkoxy would represent
OCH20CH3 th~ough O(CH2)~0CH3 or OCH20(CH2)3CH3 and the
variou~ 6~ructural i~omers embraced therein.
Alkylsulfonyl denote~ methyl~ulfonyl, e~hyl6ul-
fonyl and the different propyl~ulPonyl i~omer~.

Alkylthio. alkyl~ulfinyl, alkylamino, alkylsul-
famoyl, ~tc.. are defined in an analogou6 manner.
Preferred Co~Pound~
- Preferred for reasons of their higher herbicidal
efficacy, greater plant growth regulant activity and/or
more favorable ease of ~ynthe~is ar~:
1) Compounds of Formula I where
R is H or Cl-C3 alkyl:
2) Compound6 of Formula I where
R3 is 1 3 Y
3) Compounds of Preferred 1 where
W is O;
R i6 H;
X i~ CH3, OCH3, OC2H5, Cl, F, Br, I, OCF2H,
2 2CH2F. OCH2CHF2. OCH CF or CF
. and
Y is H, Cl-C3 alkyl, OCH3, OC2H5, CH20CH3, ~HCH3.
N(OCH3)CH3. N(CH3)~, CF3, SCH3, OCH2CH~CH2,
OCH2C-CH~ OCH2cH?ocH3~ C~2SCH3' CH2~2H5
~ LlR9 ~ Ll~ / 1 ~ 3
R\ L2R10 ~ L2 2 m \L J , OCF2~,
C-CH, C-CCH3, SCF2H or cyclopropyl;
4) Compound6 of Preferred 3 where
Ql and Q2 are identical ~nd are O or S:
12 i~ H, Cl-C2 alkyl or Cl:
R13 i~ H; and
5) Compound~ of Pre~erred 4 where
A i6 A-l;
Y is CH3, OCH3, OC2H5- CH2~CH3o ~2Hs~ 3
CH20C2H5, OCF2H, OCH2CH20CH3, cyclopropyl,
C-CH or CH(OCH3)2: and
X i~ CH3, OCH3, Cl, OC2H5, OCF2H or OCH2CF3;

~L~S~
6) Compound6 o~ Preferred 5 where Ql and ~2 are 0;
7) Compound6 of Preferred 5 where ~1 and Q2 are S:
- 8) Compound6 of Preferred 5 ~heLe Q i~ Q-l;
g) Compound6 of Preferred 5 where Q iB Q-2:
10) Compounds of Preferred S whe~e Q is ~-3;
ll) Compounds of Preferred S where Q is Q-4:
12) Compound6 o~ Preferred 5 where Q i~ Q-5;
13) Compounds o~ Pre~erred 5 where Q is Q-~:
14) Compound~ of Preferred 5 where Q is Q-7:
15) Compounds of Preferred 5 where Q is Q-8;
16) Compounds o~ Preferred 5 where Q is Q-s;
17) Compounds of Prefe~red 2 where
W i6 O,
R is H;
X i6 CH3. OCH3. OC2H5. Cl, F, Br, I, OCF2H,
CH2F. OCH2CH2F. OCH2CHF2. OCH2CF3 or CF3: and
Y i6 H. Cl C3 alkyl, OCH3, OC2H5, CH20CH3, NHCH3.
3) 3, N(CH3~2. CF3, SCH3, OCH2CH~CH ,
OCH2C--C~[. OCH2CH20CH3. CE12SCH3. CH20C2H5.
-C ~ 1 9 -C / ~CH2)m~ -CR8 ~ . OCF2H,
SCF2H, cy~lop~opyl. C-CH or C-CCH3;
18) Compounds of Preferred_17 where
E i6 a 6ingle bond:
R12 i~ H, Cl-C2 alkyl or Cl:
R13 i8 H; and
: R14 i6 H, F, Cl, Br, Cl-C2 al~yl, Cl-C2 alkoxy
vr Cl-C2 alkylthio and i6 not a~a to
the sul~onylurea bridge:
:

~259~i31 3
11
19) Compounds of Prefer ed 18 where
A i~ A-l:
Y is CH3, OC~3~ C2H5' C~2CH3' C2 5 3
~H20C2H5. OCF2H. OCH2CH20CH3. cyc1Op~opy1
C-CH or CH(OCH3)z and
X i8 CH3, OCH3~ Cl~ C2H5' CF2H ~ C~2cF3;
20) Compound6 of Preferred 19 where Q i6 Q-l;
21) Compound~ of preferred 19 where Q i~ Q-2~
22) Compound6 of Preferred 19 whe~e Q i~ Q-3;
23) Compounds of prefQrred 19 where ~ i~ Q-4;
24) Compound~ of Preferred 19 where Q i6 Q-5;
25) Compound~ of Preferred 19 where Q iR Q-6;
26) Compound6 of Preferred lg where Q i~ Q-7:
27) Compounds of Preferred 19 where Q iB Q-~:
28) Compound6 of Preferred 19 where Q i6 Q-9:
~9) Compound6 of Preferred 19 where Q i~ Q-10;
SpecificallY Preferred for rea60n6 of higheat
herbicidal efficacy and/or mo~t favorable ea~e of
6ynthesi6 are:
3-(1,3-dio~olan-2-yl)~ (4-methoxy-6-methyl-
1,3,5-triazin-2-yl)a~inocarbonyl]-2-thiophene-
~ulfonamide, m.p. 164-166C: and
0 N-~(4,6-dimethoxypyrimidin-2-yl)a~inocarbonyl]-
3-(1,3-dioxolan-2-yl)-2-thiophenesulfonamide,
m.p. 137-150C.
DETAIL~D DESCRIPTION_OF THE INV~NTION
Synthesi~
The compounds of Formula I can be prepared by one
or mo~e of the methods 6hown in Equa~ion~ 1-7.
A~ ~hown in Equation 1, compound~ of Formula I
(where ~ i6 O) can be prepared by treating 6ulfonamides
of Formula II with phenyl ester~ of N-heterocyclic-
carbamic acid6 of Formula III in the pre6ence of a

~2
Btrong organic base eOg. 1 o 8~diazabicyclo[5-4-0]-
und~ n~ (DBU).
Equa~ion 1
0 R - 0 R
Q52NH2 ' C6H5C-N-~ ~ QBo2NHc-N-A
II III I
w~erein Q. R and A are as prev~ou~ly defin~d. The
reac~ion of Equation 1 iB generally ~arried o~t in the
range of 0 to 50C .n an inert ~olvent e~g.
dioxane or acetonitrile, analogou6 to ~e~hod~ t~ught
in ~P-A 44.807. The re~uired carb~mates can be
prepared from the corre~ponding amine6, IIIa~ and
diphenyl carbonate or phenylchloroformate and a ba6e
e.g. sodium hydride as shown in Equation 2.
Equation 2.
" . R NaH 0 R
C6~5CCl ~ HNA ~ - C6H50C-NA
~ . IIIa III
- Compound6 of Formula I ~ay al~o be prepared a~
shown in ~guation 3 by ~reating ~ulfonamides o~
Formula II with the ~e~hyl e~ter of ~n N-het~ro-
~ycliccarba~ic acid of Formula IIIb ~ the presence o~
an equimolar qua~ti~y o~ tri~ethylaluminum.
Equati_n 3
0 R (CH3)3A
QS02NH2 ~ ~3~C-N-A
II IIIb
The reac~ion of Eq~ation 3 ~ best ca~ried out
at temperature~ between 25 and 83C i~ a ~olvent
e.g. methylene chloride or 1,2-dichloroethane for 12 to
95 hours under an i~ert atmosphere, a6 taugh~ i~

~L~S9~13
~3
- lEP-A ~,2~4, publ~he~ July 27, 1983. Th~ ~ethyl
5 c~rb~mat~6, IIIb. can b~ conY~ ly synthesize~ by
- tr~t~ent of the corro6pon~ hete~ocycl~c ~1noe~ o
~or~ula IIIa wieh ~i~ethyl c~rbonate or ~e~hyl
cS~lorofor~at~ ~n t~e pr~s~nce of ~ ba9te e.g. sodium
hy~r i~ .
lo Al~ernatively. ~o~pounas o~ E'or~ul~ I ean be
prepared by the r0actio~ of ~ ~ulfonylcarba~ate of
Formula IY ~ith an aminollete~ocycle of Formula $IIa as
s~own in ~quation ~. -
E~g~
o
QSo2~Hcoc6~s
loxan~
, ~V ,,
~ he reactio~ ; c~rr~ea out at 50 ~o 1t)0C ~n
solvent e.g, dioxane for 0.5 to 24 hours as taught .
~n l~P-A 4~, 807 . Tlle t~u~d ~a~bamat~6 o~ ~or~ul~ ~Y
a~e prepare~ by the re~ctio~ Qf e~e co~re6pondi~g
~ulfonami~e6 of ~or3~ul~ II w~h ~iphenylcarbonate or
p~enylchl~ofor~ate i~ the 2rese~ce of ~ e.g.
~o~ium hy~ride.
Co~poun~6 of ~or~ula I, ~here ~ , can be
~repa~e~ a~itiO~ o ~n a~prspr~a~e ~eterocycli~
a~i~e, IIIa. ~o a ~ulfo~yl i~o~io~y~ate of the
or~ula QS02NCS. T~i~ rea~on ~ be~t carri~a ou~
accor~g to ~e~ho~ ~aught i~ U.S. ~ate~ 1270~05.
~ ulfonyl ~ot~ioGyana~e6 af the for~ula
QS02NCS c~ ~e prepare~ ~ccor~g ~o t~e pro~e~ure
of ~. ~artke, Arch. ~~. 2~, 17~ (lg66).
Sulfon~ e6 o ~or~ula II u6~a ~ t~e ~rep-
~rat~o~ o~ compoun~ o~ ~or~ul~ I ~re u~@ful
~nt~r~edi~te6. T~ey ~a~ be pre~ar~ by ~ v~ri~ty of
~ethoa~ kn~wn 1~ t~e ~rt. Fo~ e~ple. ~on~a~ei~g a~

- approp~ataly 6ubstltute~ sulfonyl chlor~Q IIa w'lth
a~on~u~n hydroxi~e or ~Yamoni~ inere ~olvent e.g~
ether or tetrahydrofuran affords ~ulfonamides II as
~hown by l~quatlo~ 5~ ~n~ 5b.
S Equatio~ 5
~ther
a ) QS02Cl + 2NH3 ~ NH4Cl
IIa
b) IIa + 2NH4~0H ~ II ~ NH4Cl
The reaction of ~ulfonyl-chloride6, lIa, with
ammonia i8 best carried out ae -33 to 50C for 0.1 to
24 hour~. After removal of the ammonium chloride
by-prQduct by filtration or extra~tion with water, the
de6ired product can be i~olated by the evaporatio~ o~
the organic 601vent.
Ammonium hydroxide can be u6ed in place of
ammonia a6 in ~quation 5b. T~i~ reaction i6 widely
reported i~ tbe literature, c.f., ~ethoden Der
Orqanischen Chemie (Hoube~-~eyl), Vol. 9, ~h. 19,
edited by F. Mut~, Stuttgart, 1955.
Al~ernàtiYely, sul~ona~ides of Formula II can be
prepared by ehe reaction of a lithiu~ salt of a~
appropriately 6ub6tituted 6ulfinic acid, IIb, w~th
chlora~i~e as 6hown in ~quation 6.
Equation 6
QSo2Li + ClNH2 ~ II
Thi6 reaceion Gan be carried out usi~g the
condition6 referred to in ~he preceding reference.
Lithium ~alts of Formula IIb can al60 be
converted to ehe sul~ona~ide~ of Formula IIa by the
procedures taught in U.S. Paeent No. 4,441,9iO.
14

5~ 3
5ul~onyl c~loriae~ o~ ~ormula I~a can be
prepaE~d by ~he r~actio~ o lithiu~ ~al~s of
Pormula IIc with ~ulfuryl chloride at -50 ~o -20C i~
a~ iner~ ~olvent ~uc~ a6 tetrahydrouran or e~er a~
5 shown in ~quation 7.
~uation 7
a) QH ~ R'Li ~ QLi
IIc
10 b) QBr ~ ~'Li ~ IIc
c) IIc ~ S02C12 ~ IIa
Where R' is group e.g. butyl, phenyl, diiso-
propylamino Ol similar moiety co~mo~ly co~bine~ wi~h
lithium to form a lithiation agent. These agents and
their method of use are desceibed in N.5. Nara~imhan
and R.S. Mali. Svnthesi~, g57-~6 (1983) or i~ The
C~emistrv of O~qanolithiu~ ComPound6, Wakefield,
Pergamon Press, Oxford. 1974 or al60 H.W. Gschwend and
H.R. Rodriguez, Orq. ~eact. 26. 1 ~1978)~
Th~ sulfonyl chlorides, IIa, can be isolated by
extracting the inorganic by-product6 wit~ water
Pollowed by drying the or~anic layer over a dryi~g
agent e.g. magnesium sulfate, filtering the dried
solution and evaporation of the solvent.
Lithium salt6 of Formula IIb can be prepared by
co~tacting su1fur dioxide wit~ the lithiated
in~ermediate IIc using procedures de6cribed i~ the
above reference~ on the lithiated ~n~erm@diate6.
The for~ation o~ o~hoester~, aceeal~, cyclic
acetal~, thioacetals and their amino analogh ~here
Ql or Q2 a~e N-CH3 is widely reported in the
literature, c.f.: ~n~hetic Or~anic Che~ifitry, R~o
~agner and H.D. Zook. Ch. 8, ~ohn Wiley & ~ons. New
35 York, 1953; or Orqanic Synthe i6, V. ~igrdichian, Ch.
5, Reinhold, London, 1957.

9~:13
~6
~le ~ r~ 811y~ ng 8~:etyl BUb~e,Ut~
- t~iophene~ c~n b~ pr~par~ by ~ v~r~ty o Detho~ ~6
d~cr~ed, or ~x~mpl~ he Cbemi~try of
Heterocycl~c Compou~d~. ~41. 3, ~ by ~.D.
5 Ha~eou~b, ~.P. Hoc~ge6~ng ~n~ . Blick~p
Inter~c~ence, N.Y.. 1952. pyr~zole ~l~ehyd~ and
acetylpyrazoles can be ~r~p~r~d accor~ing to
procedu~e6 ae6~ribe~ ~n ~T~e C~mi~try of Heterocycl~c
Compoun~6", Vol. 22, odite~ by a.H. ~iley,
Inter~cience, N.Y.. 1967. Alae~yde6 ~n~ acetyl
~erivative6 o ~uran can be prspared ~ccoraing t~
~et~oa~ cite~ i~ UAdv~ncec ~n Het~rocycl~c Che~i6try~,
Vol. 7~ edited by ~.R. ~tritzky ana A. J. ~oulton,
and Vol. 30 edited by A.R. Xatcitz~y, Aeade~ic Pre6~.
N.Y., 1962 and 1982. Furth~r referenc~s to t~e .
literatu~e of heterocycli~ co~pound6 c~n be ~ound on
page~ 225-299 o~ Vol. 7 cited abov~. -
The hete~ocyclic a~ine6 of Fo~ula IIIa can beprepared by ~ethods known ~n tbe literature, or 6i~ple
~odification6 ther~of. by t~o6e ~k~lled in the art.
~or ~nstance, EP-A No. B9,224 (publi6hed Ju-ly ~7,
19B3) and W. Bra~er ~t ~1., J. A~. Che~. ~o~., 69.
3072 (1947) d~6cr~be6 ~etb~d6 or preparing
~inopy~ in~6 ~n~ tr~azl~e~ ~ubs~ t~ by ~c~t~l
a5 groups e.g. dialkyoxymethyl or 1,3-dioxolan-2-yl
~ong oth~r ~roup~. A180, ~or ~x~ple. Sout~ Afr~c~n
~atent ~pplicat~on No~. 82/50~S and 82/5671 ~6crlb0
~etbod6 for ~rep~r~ug a~nopyri~i~in~6 an~ tr~z~nQ~
~ubstitu~a ~y h~loal~yl o~ ~alo~lkylt~io ~roup~ e.g.
OCH2CH~F, OCH2CH3, SCF2H, or OCF2H, among other
group~O South Afric~n ~atent a~pl~ca~on ~3J7~34
5publ~6hed Octob~r 5, 1983) ~e6~ri~e6 ~e~bo~6 for ~he
~ynthe~i6 of ~yclopropylpyri~id~nes ~nd ~ria2ines
~Ub6titUtQ~ by ~uc~ groups R6 al~y}, halo~lk~l, i
alkoxy. haloalkoxy, ~lkyl~ino, dialkylamino or
~l~o~yalky~.
16

1;~59~i~3
The 5,6-dihydrofuroC2.3-d]pyrimidin-2-amines,
the cylcopen~atd]~yrimidin-2-amines tIIIa, A i~ A-2)
and the 6,7-dihydro-5H-pyrano[~.3-d]pyrimidin-2-amine~
(IIIa, A i6 A-3~ can be prepared as de6cri~ed in EP-
~
5 ~o. 15,6B3. The furo~2.3-d]pyrimidin-2-amine6 tIII, A
i~ A-4) are descLibed in EP-A No. 46,S77.
Compound~ of Formula IIIa, where A i6 A-5, are
de~cribed in EP-A-73,562. Compound6 of Formula IIIa,
where A is ~-6, are described in EP-~-~4,2~0.
Compound~ of Formula IIIa, where A i8 A-7, can be
prepared by methods taught in ~P-A-~125,864.
In addition, general method~ for preparing amino-
pyrimidine6 and triazine~ have been reviewed in the
following publications:
15 ~ "The Chemistry o Heterocyclic Compound~," a
seriex publi6hed by Inter6cience Publ., New York
and London;
"Pyrimidines", Vol. 16 of the 6ame serie~ by
D. J. Brown;
20 'Is-Triazines and Derivative6,ll Vol. 13 of the
same ~eries by ~. M. Smolin and L. Rapapor~;
F. C. Schaefer, U.S. Patent 3,154,547 and K. R.
Huffman and F. C. Schaefer, J. Orq. Chem., 28,
1812 (1963), which de6cribes ~he ~ynthesi~ o~
triazines.
Agri~ulturally 6ui~able 6alt6 0~ compounds o~
Formula I are also u~eful herbicide~ and can be pre-
pared in a number of way6 k~own in the ar~. For exam-
ple, metal ~alt6 can be made by contacting compound~
of Formula I with a 601ution of an alkali or alkaline
earth metal 6alt having a 6ufficiently ba~ic anion
(e.g., hydroxide, alkoxide or carbonate). Quaternary
amine salt6 can be made by ~imilar technique6.
Salts of compound~ of Fo~mula I can al~o be pre-
3S pared by excha~ge of one cation ~or another. Ca~ionicexchange can be effected by direct contact of an

~L~25~
aqueou6 solution o~ a ~alt of a compound of Formula I
; (e.g., alkali or qu~ternary amine salt) with a 801U-
tion containing the catio~ to be ~xchanged. This
method i6 mo~t ef~ective when the de~ired 6alt
containing the exchanged cation i6 in~oluble in water
and can be 6eparated by filtration.
Exchange may al~o be e~fected by pas6ing an
aqueous 601ution of a 6alt of a compound of Formula I
(e.g., an alkali metal or quaternary amine sal~)
through a column packed with a cation exchange re in
con~aining the cation to be exchanged for ~hat of ~he
original 6alt and the desired product i~ eluted from
the column. Thi~ method i~ particularly u~eful when
the desired ~alt i6 water-soluble.
Acid addition 6alt~, U8eful in this invention,
can be obtained by reacting a compound of Formula I
with a suitable acid, e.g., ~-toluenesulfonic acid,
trichloroacetic acid or the li~e.
The preparation of the compound6 of thi~
invention i8 further illu6trated ~y the following
6pecific examples. Unles~ otherwise indicated,
te~peratures are given in degree~ centi~rade.
Exam~le 1
3-(1,3-Dioxolan-2-vl)thiop~ene-2-sulfonyl chloride
To 23.4 g of 3-(1,3-dioxolan-2-yl)thiophene
(S. ~ronowitz, et al., Arkiv. Kemi., 20, 407 (196~)~
i~ 100 ml o~ anhydrou6 ~e~rahydrofuran ~a6 added
100 ml of 1.6 molar ~-butyllithiu~ in hexane, with ice
bath cooling. After stirring at room te~perature for
20 minutes the mixture wa~ cooled to -78 and sulfuryl
chloride (16.2 g) wa~ then added dropwi~e. Thi6
addition caused the suspended solid~ to fo~ a tarry
ma~s which broke up when the mixture wa~ allowed to
warm to room temperature. After ~tirring one and one
18

~s~
19
half hour6 at room temperature the mixture was cooled
to -10 and 10 ml of ethyl acetate was added drop-
wi6e. The reaction mixture was then poured into ice
water and extracted with ethyl ether. The ether
5 portion6 were combined, d~ied over magne~ium sulfate,
filtered and the ether removed in-vacuo to yield
19.6 g of an oil. Infrared ab60rption 6pectra of thi~
product ~howed paak~ at 1330 and 1180 cm
con~i6tent for the desired 6ulfonyl chlo~ide. Ma~g
6pectrum analy6is: calc. 254, found 253 (Mas6-lH) and
the pre6ence of a chlorine atom.
Example 2
3-(1~3-Dioxolan-2-Yl)thiophene-2-6ulfonamide
To 5 ml of li~uified ammonia gas di6solved in
50 ml of ~etrahydrofucan wa~ added dropwiRe with
6tirring and cooling 12.7 g of 3-(1,3-dioxolan-
2-yl)thiophene-2-6ulfonyl chloride. After ~tircing
o~ernight at ambient ~emperature, the tetrahydrofuran
wa~ removed in vacuo, water wa6 added to the re6idue
and the mixture wa6 extracted twice with 75 ml of
methylene chloride. After wa6hing the combined
methylene chlo~ide extrac~6 with water, dryi~g over
magne6ium 6ulfa~e, filtering of~ the drying agent and
evaporation of the methylene chloride, an oily æolid
residue wa6 obtained. This wa~ chromato~raphed
through silica gel u~ing 1:1 ethyl aeetate~hexane~ a6
eluant tRf 0.35). Evapora~ion of the 601vent ~ixture
yielded 2.2 g of th~ desired product, as a waxy
601id. Infrared ab60rption 6pectra ~howed peak6 at
3360, 3260, 1340 and 1140 cm 1, con~i6tent for a
primary sulfonamide. Ma~s ~pectrum analy~is: calc.
235, found 234 (Ma8s-lH).
19

59~3
2~
~xamPle 3
3-(1,3-Dioxolan-2-y~L-N-[(4-methoxv-6-meth~1-1,3,5
triazir~-2-yl)aminocarbonyll-2-thioPhene~-ulfonamide
To 0.47 g of 3-(1,3-dioxolan-2-yl~thiophene-
5 2-6ulfonamide in ZO ml of acetonitrile wa6 added
0.52 g of phenyl(4-methoxy-6-methyl-1,3,5-triazin-
2-yl)carbamate and 0.3 ml of 1,8-diazabicyclo[5.4.0]-
undec-7-ene (DBU). After ~tirring at ambient
temperature6 for two hours the ~olution wa~ diluted to
10 50 ml with water and the pH wa~ adju6ted to 3 by the
addition of hydrochloric acid. The resultant 601ution
wa6 extracted with methylene chloride and the
methylene chloride pha6e wa~ dried over magne6ium
~ulfate, filtered and evaporated. Trituration of the
re6idue with butyl chloride yielded 0.6 g of the
product, m.p. 164-166. Infrared ab60rption 6pectra
~howed peaks at 1700, 1500 and 1550 cm 1, consi~tent
for the de6ired structure.
NMR(cDcl3): ~ 2.56 ~8, CH3):
4.04 (B, OCH3);
,_0
6.43 (~, -C ~ );
4.95 ~t, ~CH2)z):
7.25 (d, thiophene3;
7.58 td, thiophene).
E~amPle 4
N- r 4~6-DimsthoxY~yri~idin-2-y~aminocarbon~11-3-
~1,3-dioxolan-2~yl2-?-thiophenesulfonamide
To 0.47 9 of 3-(1,3-dioxolan-2-yl)thiophene-
2-6ulfonamide in 20 ml of acetonitrile wa~ added 0.5 g
of phenyl (~,~-dimethoxypyrimidin-2-yl)carbamate and
0.3 ml of DBU. A~ter ~tirring for two hour6 a~
ambient temperature, 25 ml o water wa6 added to the
mixture and the 601ution wa~ acidified to pH 3 with
10% hydrochloric acid. ~he precipitated product wa~

3~3
21
removed by filtration, wa~hed with water and air dried
to yield 0.9 g of ~he ~ub3ect compound, m.p. 157-16~.
Infrared abeorption peaks at 1700, 1600, 1570 cm~~
were consis~ent for the de6ired structure.
5 N~R(C~C13) ~ 3.95 (~, CH20);
3.95 (~ C~30);
- 5.77 (~, pyrimidine);
6.44 (6, dioxolane);
7.25 (d. thiophene)~
7.57 (d, thiophene).
By u6ing the procedure6 described in the
foregoing equations and example~ or modification~
thereof, one s~illed in the art can prepare ~he
compounds shown in the following table~.
21

1~25~6:~3
22
TABL~ OF STRUCTURES
~1
2 so2N~lC-N~O
~ N--~
GENERAL STRU~TURE I
N~
P'12~ ~ ~
GENE~AL STRUCTURE I a
~a N~
E~so2NHC-N~~O
R12
GENERAL STRUCTURE I b
R~_S02NHC~ 0Z7
GENER.pL TRUCTURE I c

~59~ ~
2~
TABLE OF STRUCTURES CONTTNUED
k~ ~
S R12~02NHC-N~
GENERAL STRUCTURE I d
R12
GE~ER~L STRUCTURE I e
~SOzNHC-h-<~
~11
25GE~NERAL STRUCTUR~ I I
W ~
~ 40
// t~
~11
GENERAL STRUCTURE I Ia

24
TA~EE OF STRUCTURES CONTINU~D
~ a3
11 Y
GENERAL STRUCTURE IIb
so2~Hc~
Rll ~ 1
GENERAL STRUCTURE IIc
2~
~ SO~NH-C-N ~ O Z
~0~
GENERAL STRUCTURE III
0 ~C ~
GENERAL STRUCTURE III~
24

TABLE OF STRUCTUEIE5 C:ONTIINUED
~502NE~C~
GENE RAL STRUCTURE I I Ib
~2~
Gl~NERAL STRUCTURE IV
R~2 SO ?~ A
~ 2
~ ~1
GENERAL STRUCTURE IVa
-: a
Rl ~50227HCN-A
~, ELl;~
GE:NE:RAL STRUCTURE IVb

~25''3~3
26
T~ABLE OF _TRUCTUR~S CONTINU~D
Dl
~ S02NHC~
`N ~1
~11
G~RAL STRUCTURE V
~1 ~ SO2~HCN-A
~11
GENERAL STRUCTURE Va
ZO / 1 W
~02N~N-~
N~N
~11
GEN~RAL STR~CTURE Vb
W
N ~ SO~HCN-A
GENERAL STRUCTURE ~G
26

TABLE OF_STRUCTURES CONTINUED
~1 ~
502~CNA
GE~RAL STRUCTURE VI
[~ a
GENER~L STRUCTURE YIa
1:5
[~ -a
qENERAL STRUCTU~E VIb
Rl ~ E-SO2NHC-N ~ ~ Z
R N ~
QENERAL STRUCTURE VII
- 30 3
Rl~Rl
6 E SO2NHC N A
GENERAL STRUC~3@~ Vl1

3~:~3
28
TABL~ I
GE~AL STRUCTURe I
Rl R2 ~ W X Y Z m P._C
1,3-dioxolan-2-yl H H O CH3 CH3 CH
5 1,3-dioxolan-2-yl H H O CH3 OCH3 CH
1,3-dloxolan-2-yl H H O OCH3 w.~.3 CH
1,3-dioxolan-2-yl H H CH3 CH3 N
1,3-dioxolan-2-yl H H O CH3 OCH3
1,3-dioxolan-2-yl H H O OCH3 OCH3
10 1,3-dioxolan-2-yl H H O Cl OCH3 CH
1,3-dioxolan-2-yl H H O CH2CH3 ~HCH3
1,3-dioxolan-2-yl H H O OCF2H CH3 CH
1,3-dioxolan-2-yl H H O CF2H OCH3 CH
1,3-dioxolan-2-yl H H CF2H OCH3 N
1,3-dioxo~an-2-yl H N O OCH2CH2F CH3 N
1,3-dioxolan-2-yl H H O OCH2CHF2 CH3 N
1,3-dioxolan-2-yl H H O OCH2CF3 CH3 N
1,3-dioxolan-2-yl H H O CF3 CH3 CH
1,3-dioxolan-2-yl H H CF3 OCH3 N
1,3-dioxolan-2-yl H H CH3 NHCH3
1,3-dioxolan-2-yl H H O OCH3 ~tCH3)2 M
1,3-dioxolan-2-yl H H O OCH3 U(CH3)0CH3
1,3-dioxolan-2-yl H H O OCH3 CH20CH3
1,3-dloxolan-2-yl H H O CH3 CH20CH3 CH
1,3-dioxolan-2-yl H H O CN3 SC~3
1,3-dioxolan-2-yl H H O CH3 OGH2CH~CH2
1,3-dioxolan-2-yl H H CH3 OCH C-CH
1,3-dioxolan-2-yl H N O OCH3 CH20CH2CH3
1,3-dioxolan-2-yl H H O CH3 CH20CH2CH3
1,3-dioxolan-2-yl H H O CH3 2 2 3
1,3-dioxolan-2-yl H H O CH3 CH2 ~ 3
- 1,3-dioxola~-2-yl H H CH3 CH2SCH3
1,3-dioxolan-2-yl H H O CH3 CH2SCH3 CH
1,3-dioxolan-2-yl H H O CH3 CH(OCH3)2 CH
1,3-dioxolan-2-yl H H CH3 i~C3H7 CH

3L~59~:~L3
29
TABL~ I CO~TIWU~D
Rl R2 ~ W ~ Y Z ID p. C
__ _ _ _ _
1,3-dioxolan-2-yl H H O CH3 CH(9CH3)2 N
1,3-~ioxolan-2-yl H H O OCH3 1,3-dioxolan- CH
2-yl
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxolan-2 N
2-yl
1,3-dioxolan-2-yl H H O OCH3 4-methyl-1,3- N
dioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 4-methyl-1,3- CH
dioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 4-ethyl-1,3- CH
~ioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxan-2-yl N
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxan-2-yl CH
1,3-dioxolan-2-yl H H O OCH3 cyelopropyl CH
1,3-dioxolan-2-yl H H O OCF2H OCF2H CH
15 1,3-dioxolan-2-yl H H O ~r OCF2H CH
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl N
1,3-dioxolan-2-yl H H O F CH3 CH
1,3-dioxolan-2-yl H H O F OCH3 CH
1,3-dioxolan-2-yl H H O Br OCH3 CH
ZO 1,3-dioxolan-2-yl H H O B~ CH3 CH
1,3-dioxolan-2-yl H H O I OCH3 CH
1,3-dioxolan-~-yl H H O OCH3 cyoloprQpyl CH
1,3-dioxolan-2-yl H H o OCH2CH3 cyelopropYl N
1,3-~loxolan-2-yl H H O OCH2CH~F cyelopropyl N
1,3-~ioxolan-2-yl H H O OCH3 cyelopropyl N
1,3-dioxolan-2-yl H H O OCH3 CH(SCH3~2 N
1,3-dioxolan-2-yl H H O OCH3 CH~SCH3)2 CH
1,3-dioxolan-2-yl H H O OCH3 1,3-dithlolan- CH
2-yl
1,3-dioxolan-2-yl H H O OCH3 1 t 3-dithiolan-
2-yl
1,3-diox~lan-2-yl H H O OCH 1,3-oxathiolan- N
3 2-yl
1,3-dioxolan-2-yl H CH3 O OCH3 CH3 CH
1,3-dioxolan-2-yl H CH3 O OCH3 OCH3 CH
1 3-dioxolan-2-yl H CH3 O C~l3 C~13 CH
1,3-dioxolan-2-yl H CH3 O CH3 CH3 N
~9

~;2596~3
T~BLe I CO~TI~UED
R R2 ~ W X Y Z m P. C
1,3-dioxolan-2-yl H CH3 0 CH3 OCH3
1,3-~ioxolan-2-yl H CH3 0 OCH3 OCH3
1,3-dioxolan-2-yl H CH3 0 Cl OCH3 CH
1 3-dioxolan-2-yl H H S CH3 OCH3 CH
1,3-dioxolan-2-yl H H S CH3 CH3 CH
1,3-dioxolan-2-yl H H S OCH3 3
1,3-dioxolan-2-yl H H S OCH3 OCH3
1,3-dithiolan-2-yl H H O OCH3 CH3 CH
1,3-dithiolan-2-yl H H O CH3 CH3 CH
1,3-dithiolan-2-yl H H O Cl OCH3 CH
1,3-dithiolan-2-yl H H O OCH3 OCH3 CH
1,3-dithiolan-2-yl H H O OCH3 OCH3 N
1,3-dithiolan-2-yl H H O OCH3 CH3 N
1,3-dithiolan-2-yl H H 2 3 NHCH3 N
1,3-dithiolan-2-yl H H OCH2CH2F ~CH3 N
-CH(OCH3)2 H H O CH3 CH3 CH
-CH(OCH3)2 H H O CH3 CH3 N
-CH(OCH3)2 H H O CH3 OCH3 ~ 147-165
-CH(OCH3)2 H H O CH3 OCH3 CH
-CH(OCH3~2 H H O OCH3 OCH3 CH 156-158
-CH(OCH3)2 H H O OCH3 OCH3 ~ 135-139
-CH(OCH3)2 H H O Cl OCH3 CH 151-154
-C(CH3)(0CH3)2 H H O CH3 CH3 CH
-C(CH3)(CCH3)2 H H O CH3 ~ 3
-C~CH3)(0CH3)2 H H O CH3 OCH3 N 120-126
-C(CH3~(0CH3)2 H H O CH3 OCH3 CH lbl-144
-C(CH3)(0CH3)2 H H O OCH3 OCH3 CH 148-152
( 3~( 3 2 H H 0 OCH3 OCH N
-C(CH3)(0CH3)2 H H O Cl OCH3 CH
-CH(OC2H5)2 H H O CH3 CH3 CH
-CH(OC2H5)2 H H O CH3 3
-CH(OC2H5)2 H H O CH3 OCH~ ~
-CH(OC2H5)2 H H O CH3 OCH3 CH

1~5~ 3
31
TABL~ I CO~TINU~D
R2 R W X Y Z m ~, '9C
-CH(OC2HS~2 H H O OCH3 OCH3 CH
-CH(OC2H5)2 H H O OCH3 OCH3
-CH(SCH3)2 H H O CH3 CH3 CH
--CH(SCH3)2 H H O CH3 CH3 N
-CH(SCH3)2 H H o CH3 OCH3 N
-CH(SCH3)2 H H O OCH3 oc~3 CH
-CH(SCH3)2 H H O OCH3 OC~3 N
2-methyl-1,3- H H O CH3 CH3 CH
dloxolan-2-yl
2-methyl-1,3- H H o CH3 3
dioxolan-2-yl
2-methyl-1 3- H H O C~3 OCH3 N
dioxolan-2-yl
2-mathyl-1,3- H H ~ O CH OCH CH
dioxolan-2-yl 3 3
2-methyl-1,3- H H O OCH3 OCH3 CH
dioxolan-2-yl
2-methyl-1,3- H H O OCH3 OCH3
dioxolan-2-yl
20 2-methyl-1,3- H H O Cl OCH3 CH
dioxolan-2-yl
2-methyl-1,3- H H O Br OCH3 CH
dioxolan-2-yl
4-methyl-1,3- H H 2 5 ~HCH3
dioxolan-2-yl
4-methyl-1,3- H H O CH3 CH3 CH
dioxolan-2-yl
4-methyl-1,3- H H o CH3 3
dioxolan-2-yl
4-methyl-1, 3- H H O CH3 OCH3 N
dioxolan-2-yl
4-methyl-1,3- H H O CH OCH CH
dioxolan-2-yl 3 3
4-methyl-1, 3- H H O OCH3 OCH3 CH
dioxolan-2-yl
4-methyl-19 3- H H O OCH3 ~CH3
dioxolan-2-yl
5 4-methyl-l~3- H H O Cl OCH3 CH
dioxolan-2-yl

~9~13
32
TABLE I CO~TI~U~D
R R2 R ~ ~ Y Z m p. C
_. _ _ _
4-methyl-1,3- N H O Br OCH3 CH
~ioxolan-2-yl
1,3-oxathiolan-2-yl H H O OC2H5 ~HCH3
1,3-oxathiolan-2-yl H H O CH3 CH3 CH
1,3-oxathiolan-2-yl H H O C~3 3
1,3-oxathiolan-2-yl H ~ O CH3 OCH3 N
1,3-oxathiolan-2-yl H H O CH3 ~CH3 CH
1,3-oxathiolan-2-yl H H O OCH3 OCH3
1,3-oxathiolan-2-yl H ~ O OCH3 OCH3
1,3-oxathiolan-2-yl H H O Cl OCH3 CH
1,3-ox~thiolan-2-yl H H O OC2H5 MHC~3 N
2-methyl-1,3- H H O CH3 c~3 CH
15 dithiolan-2-yl
2-methyl-1,3- U H O CH3 3
dithiolan-2-yl
2-methyl-1,3- H H O CH3 OCH3 N
dithiolan-2-yl
2-methyl-1 3- H N O CH3 OCH3 CH
20 dithiolan-2-yl
2-methyl-1,3- H H O OCH3 OCH3 CH
dithiolan-2-yl
hexahydro-1,3-dimethyl- H U O OCH3 OCH3
pyrimidin-2-yl
hexahydro-1,3-dimethyl- H H O CH3 CH3 CH
pyrimidin-2-yl
hexahydro-1,3-dimathyl- H H O CH3 CH3 N
pyrimidin-2-yl
hexahydro~l 3-dimethyl- H H O CH3 OCH3 N
pyrimi~in-2-yl
hexahydro-1,3-dimethyl- H H O CH3 OCH3 CH
pyrimidin-2-yl
hexahydro-1,3-dimethyl- H U O OCH3 OCH3 CH
pyeimidin-2-yl
hexahydro-1,3-dimethyl- H H O C~3 OCH3 N
pyrimidin-2-yl
4 5-dimethyl-1 3- H H O CH3 CH3 CH
dioxolan-2-yl
32

~59ti~3
33
TABL~ I CO~rI~U~D
Rl R2 R W X Y Z m p. ~C
4,5-timethyl-1,3- H H CH3 CH3 N
dioxolan-2-yl
4,5-dimethyl-1,3- H H CH3 OCH3
dioxolan-2-yl
4,5-dlmethyl-1,3- H H O CH3 OCH CH
dioxolan-2-yl 3
4,5-dimethyl-1,3- H H OCH3 OCH3 CH
dioxolan-2-yl
4-ethyl-1,3- H H CH3 CH3 CH
dioxolan-2-yl
4-ethyl-1,3- H H CH3 CH3 N
dioxolan-2-yl
4-ethyl-1,3- H H CH3 OCH3 h
dioxolan-2-yl
4-ethyl-1,3- H H CH3 OC~3 CH
dioxolan-2-yl
4-ethyl-1,3- H H OCH3 OCH3 CH
dioxolan-2-yl
1,3-dimethyl-2- H H O OCH3 OCH N
imidazolinyl 3
1,3-timethyl-2- H H CH3 CH3 CH
imi~azolinyl
1,3-dimethyl-2- H H O CH3 3
imidazolinyl
1,3-dimethyl-2- H H CH3 OCH3
imidazolinyl
1,3-~imethyl-2- H H CH3 OCH3 CH
imidazolinyl
1,3-dimethyl-2- H H OCH3 OCH3 GH
imidazolinyl
1,3-dioxolan-2-yl 5-CH3 H CH3 CH3 CH
1,3-tioxolan-2-yl 5-CH3 H OC~3 CH3 CH
1,3-dioxolan-2-yl 5-CH3 H OG~3 OCH3 CH
1,3-dioxolan-2-yl 4-CH3 H OCH3 OCH3
1,3-dioxolan-2-yl 4-CH3 H OCH3 C~3 N
1,3-dioxolan-2-yl 4-CH3 H CH3 CH3 N

~5~ L3
3~
TABL~ I CO~$I~U~D
1 R~ R ~ ~ Y
-C(OCH3)3 H H OC~3 OCH3 CH
-C(OCH3)3 H H CH3 OCH3 CH
5 -C(OCH3)3 H H CH3 CH3 CH
-C(OCH3)3 H H o C1 OCH3 CH
-C(OCH3)3 H H O Br OCH3 CH
-C(OCH3)3 H H CH3 H CH
10 -C(OCH3)3 H H OCH3 H CH
-C(OCH3)3 H H OCH3 CH20C2H5 CH
-C(OCH3)3 H H O OCF2H O~H3 CH
-C(OCH3)3 H H OCH3 CH(OCH3)2 CH
-C(OCH3)3 H H CH3 C2H5 CH
-C(OCH3)3 H H CH3 CH20CH3 CH
-C(OCH3)3 H H OCH3 CH20CH3 CH
-C(OCH3)3 H H OCH3 C2H5 CH
-C(OCH3)3 H H O Cl C2H5 CH
~C(OCH3~3 H H O OCH2CH3 ~HCH3
-C(OCH3)3 H H O OCF2H CH3 CH
20 -C(OCH3)3 H H CF2~ OCH3 CH
-C(OCH3)3 H H CF2H OCN3
-C(OCH3)3 H H OCH3 cyclo-
propyl
-C(OCH3)3 H H O OCF2H OCF2H CH
25 -C(OCH3)3 H H CH3 OCH3 X
-C(OCH3)3 H H OCH3 OCH3
-C(OCH3)3 H H O CH3 3
2 5 3 2 H H OC~3 OCH3 CH
2-methoxy-1,3- H H O OCH3 OCH3 CH
dioxol~n-2-yl

~5~3
TABL~ I CO~TI~U~D
Rl R2 R W X Y Z m~ C
( 2 5)3 OCH3 OCH3 CH
-C(OC2H5)3 H H CH3 OC~3 CH
5 -C(OC2H5)3 H H CH3 CH3 CH
-C(OC2H5)3 H H O Cl OCH3 CH
-C(OC2H5)3 H H O Br OCH3 CH
( 2 5 3 H CH3 H CH
-C(OC2H5)3 H H OCH3 H CH
10-C(OC2H5)3 H H OCH3 CH20C2H5 CH
-C(OC2H5)3 H H O OCF2H OCH3 CH
-C(OC2H5)3 ~ ~ OCH3 CH(OCH3)~ CH
-C(OC2H5)3 H H CH3 C2H5 CH
-C(OC2H5)3 H H CH3 CH20CH3 CH
15-C(OC2H5)3 H H OCH3 C~20CH3 CH
-C(OC2H5)3 H H OCH3 C2H5 CH
-C(OC2H533 H H O Cl C2H5 CH
-C(OC2H5)3 H H O OCH2CH3 ~HCH3
-C(OC2H5)3 H H O OCF2H CH3 CH
20-C(OC2H5)3 H H ~F2H OC~3 CH
-C(OC2h5)3 H H CF2H OCH3
-C(OC2H5)3 H H O OCH3 c~clo-
C(OC2 5)3 H H O OCF2H OCF2H CH
25-C(OC2H5)3 H Y CH3 OCH3
-C(OC2H5)3 H H OC~3 OCH3
( 2 5 3 H H O CH3 3
-c(oCH3)~0cH2Hs)2 OCH 3 oc~3 CH
2-ethoxy-1,3- H H O OCH 3 oc~3 CH
dioxolan-2-yl

~59~3
36
TABLE I CONTlNUED
Rl R2 R W X Y Z m.P. C
-~(9CH2CH2CH3)3 H H O OC~ OCH3 CH
~C(OCH2CH2CH3)~ ~ H O CH3 OCH3 CH
-C~OCH2CH2CH3)3 H H O CH3 CH3 SH
-C(OC~2CH2cH3)3 H H O Cl OCH3 C
-C(OCH2CH2CH3)3 H H O CH3 3
-C(OCH2CH2CH3)3 H H O OCH3 OCH3 N
-C(C2H5~(0CH3)2 H H O OCH3 O~H3 CH
~C(C2H5)(0CH3)2 H H O CH3 OCH3 CH
-C(C2H5)(0CH3)2 H H O CH3 ~H3 CH
-C(C2H5)(0CH3)2 H H O CH3 oc~3 N
-C(C~H5)(0CH3)2 H H O OC~ OCH3 N
-C(n-C3~ )(05H3)2 H H O OCH3 OCH3 CH
2-ethyl-1,3- H H O OCH3 OCH3 C~
dioxolan-2-yl
2-ethyl-1,3- H H O CH3 OCH3 C~l
diox lan-2-yl
20 2-ethy~ 3- H H O CH3 OCH3 N
~ioxolan-2-yl
2-propyl-1,~- H H O OCH3 ,~CH3 CH
dioxolan-2-yl
2-propyl-1,3- H H O CH3 ~CH3 CH
dioxolan-2-yl
25 2_p~opyl-1,3~ H H O C~ O~H3 N
dloxolan-2-yl
1,3-dioxolan-2-yl H H O CCH3 C~CH CH
1,3-dloxolan-2-yl H H O OC~ CF3 CH
1~3-dioxolan-2yl H H O OCH~ SCF~H CH
30 1,3-dioxolan-2-yl ~ H O ~H~F O~H3 CH
1,3-dioxolan-2-yl H ~ O OCH3 H C~
1,3-dioxolan-2-yl H H O CH3 0~2H5 CH
C(OCH3)3 H H O F O~H3 CH
C(OCH3)3 H H O I OCH3 CH
35 C(DCH3)3 H H O OCH3 C~H CH
36

~2~ 3
TABL~ Ia
G~U~RAL STRUCTV~C Ia
Rl R12 R W X Y Z m p. C
1,3-dioxolan-2-yl H H O CH3 CH3 CH
5 1,3-dioxolan-2-yl H H O CH3 OCH3 CH
1,3-~ioxolan-2-yl H H OCH3 OCH3 CH
1,3-dioxolan-2-yl H H O CH3 3
1,3-dioxolan-2-yl H H O CH3 OC~3
1,3-dioxolan-2-yl H H O OCH3 OCH3 N
10 1,3-dioxolan-2-yl H H O Cl OCH3 CH
1,3-dioxolan-2-yl H H O CH2CH3 ~HCH3
1,3-dioxolan-2-yl H H O OCF2H c~3 CH
1,3-dioxolan-2-yl H H O CP2H O~H3 CH
1,3-dioxolan-2-yl H H O CF2H OCH3
I5 1,3-dioxolan-2-yl H H O OCH2CH2F CH3 N
1,3-dioxolan-2-yl H H O OCH2CHF2 CH3 N
1,3-dioxolan-2-yl H H O C~2cF3 CH3
1,3-dioxolan-2-yl H H CF3 CH3 CH
1,3-dioxolan-2-yl H H O CF3 OCH3
1,3-dioxolan-2-yl H ~ CH3 WHCH3 N
1,3-dioxolan-2-yl H H O OCN3 N(CH3)2
1,3-dioxolan-2-yl H H OCH3 ~(CH3)0CH3
1,3-dioxolan-2.yl H H O OCH3 CH20CH3
1,3-dioxolan-2-yl H H CH3 CH20CH3 CH
1,3-dioxolan-2-yl H H O CH3 SCH3 N
1,3-dioxolan-2-yl H H O CH3 OCH2CH=CH2
1,3-dioxolan-2-yl H ~ O CH3 OCH C-CH
1,3-dioxolan-2-yl H H OCH3 CH20CH2CH3
1,3-dioxolan-2-yl H H O CH3 CH20C2H5
1,3-dioxolan-2-yl H H CH3 2 2 3
1,3-~ioxolan-2-yl H H O CH3 2 2 3
1,3-dioxolan-2-yl H H O CH3 CH2SCH3 N
1,3-dioxolan-2-yl H H O CH3 CH2SCH3 CH
1,3-dioxolan-2-yl H H O CH3 CH(OCH3)2 CH
1,3-dioxolan-2-yl H ~ o CH3 3 7 CH

38
TA~L~ Ia CO~TI~U~D
Rl R12 R W X Y Z ~ e _~
1,3-dioxolan--2-yl H H O CH3 CH(OCH~)2 N
: 1,3~dioxolan-2-yl H H O OCH3 1,3-dioxolan-2-yl CH
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 4-methyl~1,3- N
dioxolan-2 yl
1,3-dioxolan-2-yl H H O OCH3 4-methyl-1,3- CH
dioxol&n-2-yl
1,3-dioxolan-2-yl H H O OCH3 4-ethyl-1,3- C~
dioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxan-2-yl
1,3-dioxolan-2-yl H H O OCH3 1,3-aioxan-2-yl CH
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl CH
1,3-dioxolan-2-yl H H O OCF2H OCF2H CH
1,3-dioxolan-2-yl H H O ~r OCF2H CH
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl N
1,3-dioxolan-2-yl H H O F CH3 CH
1,3-dioxolan-2-yl H H O Y OCH3 CH
1,3-dioxolan-2-yl H H O Br OCH3 CH
20 1,3-dioxolan-2-yl H H O Br ~H3 C~
1,3-~io~olan-2-yl H H O I OCH3 C~
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl CH
1,3-dioxolan-2-yl H H O OCH2CH3 cyclopropyl
1,3-~ioxolan-2-yl H H O OCH2CH2F cyclDproP
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl
1,3-dioxolan-2-yl H H O OCH3 CH(SCH3)2
1,3-dioxolan-2-yl H H O QC~3 CH(SCH3)2 CH
1,3-dioxolan-2-yl H H O OCH3 1,3-dithiolan-2-yl CH
1,3-dioxolan-2-yl H H O OCH3 1,3-dithiolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 1,3-oxathiolan-2-yl ~
1,3-dioxolan-2-yl H CH3 0 OCH3 CN3 CH
1,3-~loxolan-2-yl H CH3 0 OCH3 OCH3 CH
1,3-dioxolan-2-yl H CH3 0 CH3 CH3 CH
1~3-dioxolan-2-yl H CH3 0 CH3 C 3
38

~Sg~
A~L~ Ia CO~TI~U~D
Rl R12 R W X Y Z ~ p. C
1,3-dloxolan-2-yl H CH~ O CH3 OCH3 N
1,3-dioxolan-2-yl H CH3 O OCH3 OCH3
5 1,3-dioxolan-2-yl H 3 OCH3 CH
1,3-dioxolan-2-yl H H S CH3 OCH3 CH
1,3-dioxolan-2-yl H H S CH3 CH3 CH
1,3-dioxolan-2-yl H H S O~H3 3
l,3-~ioxolan-2-yl H H S OCH3 CCH3 N
lO 1,3-dithiolan-2-yl H H O OCH3 CH3 CH
1,3-dithiolan-2-yl H H O CH3 CH3 CH
1,3-~ithiolan-2-yl H H O Cl OCH3 CH
1,3-~ithiolan-2-yl H H O W H3 OC~3 CH
1,3-dithiolan-2-yl H H O OCH3 OCH3 N
1,3-~ithiolan-2-yl H H O OCH3 CH3 N
1,3-dithiolan-2 yl H H 2 3 NHCH3 N
1,3-dithiolan-2-yl H H Q OCH2CH2F ~HC 3 N
-CH(OCX3)2 H H O CH3 c~3 CH
-CH(OCH3)2 H H O CH3 3
20 -CH(OCH3)2 H H O CH3 OCH3
-CH(OCH3)2 H H CH3 OCH3 CH
-CH(OCH3)2 H H O OCH3 OCH3 CH
-CH(OCH3)2 H H O OCH3 OC~3
-CH(OCH3)2 H H O Cl OCH3 CM
-C(CH3)(0CH3)2 H H O CH3 CH3 CH
-C(CH3)(0CH3)2 H H o CH3 3
-C(CH3)(0CH3)2 H H O CH3 OCH3
-C(CH3)(0CH3)2 H H O CH3 OCH3 CH
-C(CH3)(0CH3)2 H H O OCH3 OCH3 CH
-C(CH3)(0CH3)2 H H O OCH3 OCH3 N
-C(CH3)(0CH3)2 H H O Cl OCH3 CH
-CH(OC2H5)2 ~ H O CH3 CH3 CH
-CH(OC2H5)2 H H O CH3 3
-CH(OC2H5)2 H H O CH3 OCH3 N
-CH(OC2H5~2 H H O CH3 OCH3 CH

~ 2 t~ 3
TABL~ Ia COUTI~VED
Rl Rl2 R W ~ Y Z m P. C
-CH(C2H5)2 ~ H O OCH3 OCH3 CH
-CH(OC2H5)2 H H O C~3 OCH3 N
5 -CH(SCH3)2 H H O CH3 CH3 CH
-CH(SCH3)2 H N O CH3 CH3 N
-CH(SCH3)2 H N O CH3 OCH3 N
-CH(SCH3)2 H H O OCH3 05H3 CH
-CH(SCH3)2 H H O OCN3 OCH3 N
2-metbyl-1,3- H H O CH3 CH3 CH
~ioxolan-2-yl
2-methyl-1,3- H H O CH3 3
~ioxolan-2-yl
2-methyl-1,3- H H O CH3 OCH3 N
dioxolan-2-yl
2-methyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
2-methyl,-1,3- H H O OCH3 OCH3 CH
dioxolan-2-yl
2-methyl-1,3- H H O OCH3 OCH3 N
dioxolan-2-yl
20 2-methyl-1,3- H H O Cl OCH3 CH
dioxolan-2-yl
2-meth~1-1,3- H H O ~r OCH3 CH
dioxolan-2-yl
4-methyl-1,3- , h ~ O OC2H5 ~HCH3 N
dioxolan-2-yl
4-methyl--1,3- H N O GH3 CH3 CH
dioxolan-2-yl
4-methyl-1 3~ H H O CH3 CH3 N
dioxolan-2-yl
4-methyl-1,3- H H o CH3 OC~3
dioxolan-2-yl
4-mathyl-1 3- ~ ~ 0 CH3 OCN3 CH
dioxolan-2-yl
4-methyl-1,3- H H o C~3 OCH3 CH
dioxolan-2-yl
4-methyl-1,3- ~ H O OCH3 OCH3 N
dioxolan-2-yl

~2~59~3
41
TABLE Ia CO~TI~UED
_ ~12 R W X Y Z m~e~_~
4-methyl-1,3- H H O Cl OCH3 CH
dioxolan-2-yl
5 4-methyl-1,3- H H O Br OCH3 CH
dioxolan-2-yl
1,3-oxathiolan-2-yl 2 S 3 N
1,3-oxathiolan-2-yl H H O CH3 3
1,3-oxathiolan-2-yl H H O CH3 CH3 N
1,3-oxathiolan-2-yl H H O CH3 OCH3
1,3-oxathiolan-2-yl H H O CH3 OCH3 CH
1,3-oxathiolan-2-yl H H O OCH3 OCH3 CH
1,3-oxathiolan-2-yl H H O OCH3 OCH3 N
1,3-oxathiolan-2-yl H H O Cl OCH3 CH
1,3-oxathlolan-2-yl H H O OC2H5 ~HCH3
2-methyl-1,3- H H O CH3 CH3 CH
dithiolan-2-yl
2-methyl-1,3- H H O CH3 CH3 N
dithiolan-2-yl
2-methyl-1,3- H H O CH3 OCH3 N
dithiolan-2-yl
2-methyl-1,3- H H O CH3 OCH3 CH
dithiolan-2-yl
2-methyl-1,3- H H O OCH3 OCH3 CH
dithiolsn-2-yl
hexahydr~-1,3-dimethyl- H 3 3
25 py~imiflin-2-yl
hexahydro-1 3-dimethyl- H H O C~3 CH3 CH
pyrimidin-2-yl
hexahydro-1~3-dimethyl- H H O C~3 3
pyrimidin-2-yl
hexahy~ro-1,3-dimethyl- H H O CH3 OCH3 N
30 pyrimidin-2-yl
hexahydro-1,3-dimethyl- H H O CH3 OCH3 CH
pyri~idin-2-yl
hexahydro-1,3-dimethyl- H 3 3 CH
pyrimidin-2-yl
hex~hydro-1,3-dimethyl- H 3 3 N
35 pyrimidin-2-yl
41

~lL;Z5~ 3
42
TABL~ I~ CO~TI~UE~
Rl R12 ~ W X Y Z m ~ ~C
4,5-dimethyl-1,3- H H CH3 CH3 CH
dioxolan-2-yl
4,5-dimethyl-1,3- H H O C~3 3
dioxolan-2-yl
4,5-dim~thyl-1,3- H H CH3 OCH3
~iox~1an-2-yl
4,5-dimethyl-1,3- H H CH3 O~H3 CH
dioxolan-2-yl
4,5-~im~thyl-1,3- H H OCH3 OCH3 CH
dioxolan-2-yl
4-ethyl-1,3- H H CH3 CH3 CH
dioxolan-2-yl
4-ethyl-1,3- H H o CH3 3
~ioxolan-2-yl
~5 4-ethyl-1,3- H H CH3 OCH3 N
dioxolan-2-yl
4-ethyl-1,3- H H O CH OCH3 CH .
dioxolan-2-yl 3
4-ethyl-1,3- H H O OCH OCH3 CH
dioxolan-2-yl 3
1,3-dimethyl-2- H H OCH3 OCH3
imidazolinyl
1,3-dimethyl-2- H ~ CH3 CH3 CH
imidazolinyl
1,3-dimethyl-2- H H O C~3 3
imi~azolinyl
1,3-di~ethyl-2- H H CH3 OC~3 N
imidazolinyl
1,3-dimethyl-2- H H 3 OCH3 CH
imidazolinyl
1,3-dimethyl-2- H H OCH3 OCH3 CH
imida201inyl
1,3-dioxolan-2-yl 3 CH3 CH3 CH
1,3-dioxolan-2-yl 3 OC~3 CH3 CH
1,3-~ioxolan-2-Y1 3 OCH3 OCH3 CH
1,3-dioxolan-2-yl 3 OCH3 OCH3 N
l~3-~ioxolan-2-yl 3 OCH3 3
1,3-dioxolan-2-yl 3 CH3 3
42
I

43
TABLE Ia CO~TI~UED
Rl R12 R W a~ Y Z m ~. C
-C(OCH3)3 H H OC~3 OCH3 CH
-C(OCH3)3 H H CH3 OC~3 CH
-C(OCH3)3 H H CH3 CH3 CH
-C(OCH3)3 H H O Cl OCH3 CH
-C(OCH3)3 H H O Br OCH3 CH
-C~OCH3)3 H H O CH3 ~ CH
-CtOCH3)3 H H OCH3 H CH
-C(OCH3)3 H H OCH3 CH20C2H~ CH
-C~OCH3)3 H H O OCF~H OCH3 CH
-C(OCH3)3 H H OCH3 CH(OCH3)~ CH
-C(OCH3)3 H H CH3 C2H5 CH
-C(OCH3)3 H H CH3 CH20CH3 CH
-C(OCH3)3 H H O OCH3 CH20CH3 CH
-C(OCH3)3 H H OCH3 C2~5 CH
-C(OCH3)3 H H O Cl C2H5 CH
-C(OCH3)3 H H O OCH2CH3 NHCH3
-C~OCH3)3 H H O OCF2~ c~3 CH
-C(OCH3)3 H H CF2~ OCH3 CH
-C(OCH3)3 H H ~F2H OCH3
-C(OCH3)3 H ~ ~ oc~3 cyclo-
propyl
-C(OCH3)3 H H o OCF~H OCF2H CH
25 -C(OCH3)3 H H CH3 OCH3
~C(OCH3~3 H H OCH3 OCH3
-C(OCH3)3 H H o CH3 3
43

9~
44
TABLE Ia CO~TI~UFD
Rl R12 R W ~ Y Z tJI p. S
( 2 S 3 H H OCH3 OCH3 CH
-C(OC2H5)3 H H CH3 OCH3 CH
5 -C(OC2H5)3 H H CH3 CH3 CH
-C(OC2H5)3 H H O C1 OCH3 CH
2 5 3 H H o Br OCH3 CH
-C[OC2H5)3 H H CH3 H CH
-C1C2H5)3 H H OC~3 H GH
-C(OC2H5)3 H H OCH3 CH20C2H5 CH
-C(OC2H5)3 H H O OCF2H OCH3 CH
-C(OC2H5)3 H H OCH3 CH(OCH3)2 CH
1 2 5)3 H CH3 C2HS CH
-C(OC2H5)3 H H CH3 CH20CH3 CH
15-C(OC2H5)3 H H OCH3 CH20CH3 . CH
( 2 5)3 H H OCH3 C2H5 CH
-C(OC2H5)3 H H O C1 C2H5 CH
-C(OC2H5)3 H H O OCH2CH3 NHCH3 M
-C(OC2H5)3 H H O OCY2H CH3 CH
20-C(OC2H5)3 H H eF2~ OC~3 CH
-C(OC2H5)3 H H CF2H OCH3
-C(OC2H5)3 H H OCH3 cyclo-
propyl
2 5 3 H H O OCP2H 2
25-C(OC2H5)3 H H CH3 OCH3
-C(OC2H5)3 H H OCH3 OCH3
2 5 3 H O CH3 3

~259~;~3
Rl R12 R W X Y Z m.P. C
s -C(OCH2CH2CH~)3 H H O DCH3 OCH~ CH
-C(OCH~CH2CH3)3 H H O CH3 OCH3 CH
CH CH CH H H O CH3 C~3 CH
-C(O ~ ~ 3~3
-C(OCH2CH2CH3)3 ~ H O Cl OCH3 CH
~C(OCH2CH2c~3)3 H H O CH3 OCH3 ~ N
-C(OCH2CH2CH3~3 H H O OCH3 CCH3 N
-C(C2H5)(0CH3)2 H H O OCH3 QCH3 OH
-C(C2H5)(0CH3)2 H H O CH3 OCH3 CH
-ctC2Hs)(~cH3)2 H H O CH3 CH3 CH
-C(C2H5)(0CH3)2 H O CH3 GCH3 N
-C(C2H5)(0CH3)2 H H O OCH3 OCH3 N
-C~n-C3H7)(0CH3)2 H H O OCH3 OC ~ CH
2-ethyl-i,3- H H 0 OCH3 OCH3 CH
dioxolan-2-yl
2-ethyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
2_ethyl-1,3~ H H O CH3 OCH3 N
dioxolan-2-yl
2-propyl-1,3- H H O OCH3 OC~ CH
dioxolan-2-yl
2-propyl-1,3- H H O ~ Q~H3 CH
dioxolan-2-yl
2~ 2_propyl-1.3~ H H D ~ ~3 N
dioxolan-2-yl
1,3-dioxolan-2-yl C2H5 H O OCH3 0~3 CH
1,3-dioxolan-2-yl Cl H O OCH3 OC~ CH
3~
~5

~L~S~ 3
46
TABLE Ib
GE~eRAL 3TRUCTURE Ib
Rl R12 R W ~ Y ~ m C
1,3-dioxolan-2-yl N H O CH3 CH3 CH
1,3-dioxolan-2-yl H H O CH3 OCH3 GH
1,3-dioxolan-2-yl H H OCH3 OCH3 C~
1,3-~ioxolan-2-yl H H O CH3 3
1,3-dloxolan-2-yl H H O CH3 ~CH3 N
1,3-dioxolan-2-yl H H O OCH3 OCH3
10 1,3-dioxolan-2-yl H H O Cl OCH3 CH
1,3-dioxolan-2-yl H H O CH2CH3 ~HCH3 N
1,3-dioxolan-2-yl H H O OCF2H CK3 CH
1,3-dioxolan-2-yl H H O CF2H OCH3 CH
1,3-dioxolan-2-yl H H O CF2H OCH3 N
1,3-dioxolan-2-yl H H O OCH2CH2F CH3 N
1,3-dioxolan-2-yl ~ H O OCH2CHF2 CH3 N
1,3-dioxolan-2-yl H 2 3 3 N
1,3-dioxolan-2-yl H H O CF3 CH3 CH
1,3-dioxolan-2-yl H H O CF3 OCH3
1,3-dioxolan-2-yl H H O CH3 3
1,3-dioxolan-2-yl H H O OCH3 3 2
1,3-dioxolan-2-yl H H 9 OCH3 ~(CH3)0CH3
1,3-dioxolan-2-yl H H O OCH3 CH20CH3
1,3-dioxolan-2-yl H H CH3 CH20CH3 CH
1,3-dioxolan-2-yl H H C~3 SCH3
1,3-dioxolan-2-yl H H CH3 OCH2CH=CH2 N
1/3-dioxolan-2-yl H H CH3 OCH C-CH
1,3-dioxolan-2-yl H H O OCH3 CH20CH~CH3
1,3-dioxolan-2-yl H H CH3 CH~OC2H5 N
1,3-~ioxolan-2-yl H H O CH3 2 2 3
1,3-dioxolan-2-yl H H O CH3 2 2 3
1,3-dioxolan-2-yl H H CH3 CH2$CH3 N
1,3-dioxolan-2-yl H H O CH3 CH2SCH3 CH
1,3-dioxolan-2-yl H H CH3 CH(OCH3)2 CH
1,3-dioxolan-2-yl H H O CH3 3 7 CH
4~

~259~i~3
~7
~L~
R 12 W X Y Z m ~. C- - -
1,3-dioxolan-2-yl H H O CH3 CH(OCH3)2
1,3-~loxolan-2-yl H H O OCH3 1,3-~ioxolan-2-yl CH
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 4-methyl-1,3-
dioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 4-methyl-1,3- CH
~ioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 4-ethyl-1,3- CH
dioxolan-2-yl
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxol-2-yl
1,3-dioxolsn-2-yl H H O OCH3 1,3-dioxol-2-yl CH
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl CH
1,3-dioxolan-2-yl H H O OCF2H OCF2H CH
1,3-dioxolan-2-yl H H O Br OCF2H CH
15 1,3-dioxolan-2-yl H H O OCH3 cyclopropyl
1,3-dioxolan-2-yl H H O F CH3 CH
1,3-dioxolan-2-yl H H O F OC~3 CH
1,3-dioxolan-2-yl H H O Br OCH3 C~
1,3-dioxolan-2-yl H H O Br CH3 CH
20 1,3-dioxolan-2-yl H H O I OCH3 CH
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl CH
1,3-dioxolan-2-yl H H 2 3 cyclopropyl
1,3-dioxolan-2-yl H H o OCH2CH2F cyclopropyl
1,3-dioxolan-2-yl H H O OCN3 cycloprop~l
1,3-dioxolan-2-yl H H O OCH3 CH(SCH3~2
1,3-dioxolan-2-yl H H O OCH3 CH(SCH3~2 CH
1,3-dioxolan-2-yl H ff O OCH3 1,3-~ithiolan-2-yl CH
1,3-dioxolan-2-yl H H O OCH3 1,3-dithiolan-2-yl
1,3-~ioxolan-Z-yl H H O OCH3 1,3-oxathiolan-2-yl
1,3-di3xolan-2-yl H CH3 0 OCH3 CH3 CH
1,3-dioxolan-2-yl H CH3 0 OCH3 OCH3 CH
1,3-dioxolan-2-yl H CH3 0 CH3 c~3 CH
1,3-dioxolan-2-yl H CH3 0 CH3 3
1,3-~ioxolan-2-yl H CH3 0 CH3 OCh3
1,3-dioxolan-2-yl H CH3 0 OCH3 oc~3 N
47

9~3
48
TABL~ Ib CO~TILU~D
Rl R12 R W ~ Y Z m p. C
l,3-dioxolan-2-yl H CH3 O Cl OCH3 CH
1,3-dioxolan-2-yl H H 5 CH3 OCH3 CH
5 1,3-d~oxolan-2-yl H H S CH3 CH3 CH
l,3-dioxolan-2-yl H H S OCH3 3
1,3-dioxolan-2-yl H H S OCH3 OCH3
1,3-dithiolan-2-yl H H O OCH3 CH3 CH
1,3-dithiolan-2-yl H H O CH3 c~3 CH
10 1,3-~ithiolan-2-yl H H O Cl OCH3 CH
1,3-dithiolan-2-yl H H O OCH3 OCH3 CH
1,3-~ithiolan-2-yl H H O OCH3 OCH3
1,3-dithiolan-2-yl H H O OCH3 CH3 N
1,3-dithiolan-2-yl H H 2 3 ~HCH3 N
1,3-dithiolan-2-yl H H 2 2 3
-CH(OCH3)2 H H O CH3 c~3 CH
-CH(OCH3)2 H H O CH3 CH3 N
-CH(OCH3)2 H H O CH3 OCH3 N
-CH(OCH3)2 H H O CH3 OCH3 C~
20 -CH(OCH3)2 H H O OCH3 oc~3 CH
-CH(OCH3)2 H H o OCH3 OCH3
-CH(OCH3)2 H H O Cl OCH3 CH
-5(CH3~(0CH3)2 H H O CH3 CH3 CH
-C(CH3)(0CH3)2 H H o CH3 3
2 -C r CH3)(0CH3)2 H H O CH3 oc~3 N
-C(CH3)(0CH3)2 H H O CH3 OCH3 CH
-C(CH3)(0CH3)2 H H O OCH3 OCH3 CH
-C~CH3)(0CH3)2 H H O OCH3 OC~3
-C~CH3~(0CH3)2 H H O Gl OCH3 CH
30 -CH(OC~H~2 H H O CH3 c~3 CH
-CH(OC2H5)2 H H o CH3 3
-CH(OC2H5)2 H H O CH3 OCH3
-CH(OC2H5)2 H H O CN3 O~H3 CH
-CH~OC2H5)2 H H O OCH3 OCH3 CH
-CH(OC2H5)2 H H O OCH3 OCH3 N
48

~S~ .3
49
TA~LE Ib CO~TI~U~D
Rl R12 R ~ ~ Y Z p C
-CH(SCH3)2 H H CH3 CH3 CH
CHtSCH3)2 H H O CH3 3
5 -CH(SCH3)2 H H CH3 OCH3 N
-CH(SCH3)2 H H OCH3 OCH3 CH
-CH(SCH3)2 H 3 3 N
2-methyl-1,3- H H O CH3 CH3 CH
dioxolan-2-yl
lO 2-methyl-1,3- H H CH3 CH3 N
dioxolan-2-yl
2-methyl-1,3- H H O CH3 OCH3
dioxolan-2-~1
2-methyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
2-methyl-1,3- H H O OCH3 OCH3 CH
dioxolan-2-~1
2-methyl-1,3- H H O OCH3 OCH3 N
dioxolan-2-yl
2-methyl-1,3- H H O Cl OCH3 CH
dioxolan-2-yl
20 2-methyl-1,3- H H O Br OCH CH
dioxolan-2-yl 3
4-methyl-1,3- H H O OC2H5 ~HCH3
dioxol~n-2-yl
4-methyl-1,3- H H O CH3 CH3 CH
~ioxolan-2-yl
4-methyl-1,3- H H CH3 CH3 N
~ioxolan-2-yl
4-methyl-1,3- H H O CH3 OC~3
d~oxolan-2-yl
4-methyl-1,3- H H O CH3 OCH3 GH
dioxolan-2-yl
4-methyl-1,3- 3 3
dioxolan-2-yl
4-methyl-1,3- H H OCH3 O~H3 N
dioxolan-2-yl
4-methyl-1,3- H H O Cl OCH3 5H
dioxolan-2-yl
35 4-methyl-1,3- H H O Br OCH3 CH
dioxolan-2-yl
49

~259~j~l3
so
TAa~ Ib CO~TI~U~D
R~ 2 R W X Y Z p. ~C
1,3-oxathlolan-2-yl H H O C2H5 ~HC~l3
1,3-oxathiolan-2-yl H H O CH~CH3 C~
1,3-oxathiolan-2-yl H H O CH3 3
1,3-oxathiolan-2-yl H H O CH3OCH3
1,3-oxathiolan-2-yl H H O CH3 OCH3 CH
1,3-oxathiolan-2-yl 3 3
1,3-oxathiolan-2-yl 3 3
10 1~3-oxathiolan-2-yl H H O Cl 3
1,3-oxathiolan-2-yl H H O C2HS ~HCH3 N
2-methyl-1,3- H H O CH3 3
dithiolan-2-yl
2-methyl-1,3- H H O CH3 3
15 dithiolan-2-yl
2-methyl-1,3- H H O CH3OCH3
dithiolan-2-yl
2-methyl-1,3- H H O CH3OC~3 CH
dithiolan-2-yl
2-methyl-1,3- H ~ O OCH3 OCH3 CH
dithiolan-2-yl
hexahydr~-1,3-dimethyl- H 3 3
pyrimidin-2-yl
hexahy~ro-1,3-dimethyl- H H O CH3 CH3 CH
pyrlm~din-2-yl
hexahydro-1,3-~imethyl- H H O CH3 3
pyrimi~in-2-yl
hexahydro-1,3-dimethyl- H H CH3 OCH3 N
pyrimidin-2-yl
hexahydro-1,3-~imethyl- H H O CH3 OCH3 C~
pyrimidin-2-yl
hexahydro-1,3-dimethyl- H H O OCH3 OCH3 CH
30 pyrimidin-2-yl
hexahydro-1,3-timsthyl- H 3 3
pyrim~din-2-yl
4,5-dimethyl-1,3- H H O CH3 CH3 CH
dioxolan-2-yl
4,5-dimethyl-1,3- H H CH3 CH3 N
35 dioxolan-2-yl

~S9Ç~j~3
51
TABLE_Ib CO~TI~UaD
Xl R12 R W X Y Z m
4,5-dimethyl-1,3- H H CH3 OCH3 N
dioxolan-2-yl
4,5-dim~thyl-1,3- H H CH3 OCH3 CH
dioxolan-2-yl
4,5-dimethyl-1,3- H H ~CH3 OCH3 CH
dioxolan-2-yl
4-ethyl-1, 3- H H CH3 CH3 CH
dioxolan-2-yl
4-ethyl-1,3- H H CH3 CH3 N
dioxolan-2-yl
4-ethyl-1, 3- H H C~3 OCH3
dioxolan-2-yl
4-ethyl-1,3- H H CH3 OC~3 CH
dioxolan-2-yl
4-ethyl-1,3- H H O OC~3 OCH3 . CH
dioxolan-2-yl
1,3-dimethyl-2- H H OCH3 OCH3 N
imidazollnyl
1,3-dimethyl-2- H H CH3 CH3 CH
imidazolinyl
1,3-dimethyl-2- H ~ C~3 CH3 N
imidazollnyl
1,3-dimathyl-2- H ~ CH3 OCH3
imidazolinyl
1,3-~l~ethyl-2- H H C~3 OCH3 CH
imidazolinyl
z5 1,3-dimethyl-2- H H OCH3 OC~3 CH
lmidazolinyl
1,3-~ioxolan-2-yl 3 CH3 CH3 C~
1,3-dioxolan-2-yl 3 OCH3 CH3 CH
1~3-dloxolan-2-yl 3 OC~3 OCH3 CH
1,3-dioxolan-2-yl 3 OCH3 O~H3
1,3-dioxolan-2-yl 3 OCH3 CH3 N
1,3 dioxolan-2-yl 3 C~3 C~3

~L7~5~3~
52
T~BL~ Ib CO~TI~U~D
Rl Rl2 R W ~ Y Z m p. C
-C(OCH3)3 H H OC~3 OCH3 CH
-C(OCH3)3 H H C~13 OCH3 CH
5 -C(OCH3)3 H H CH3 CH3 CH
-C(OCH3)3 H H O Cl OCH3 CH
-C(OCH3)3 H H O Br OCH3 CH
-C(OCH3)3 H H CH3 H CH
~C(OCH3)3 H H OCH3 H CH
-C(OCH3)3 H H OCH3 CH20C2H5 CH
-C(OCH3)3 H H O CF2H oc~3 CH
-C(OCH3)3 H H OCH3 CH(OCH3)2 CH
-C(OCH3)3 H H C~i3 C2H5 CH
-C(OCH3)3 H H CH3 CH20CH3 CH
-C(OCH3)3 H H OCH3 C~120CH3 CH
-C(OCH3)3 H H OCH3 C2H5 CH
-C(OCH3)3 H H O Cl C2H5 CH
-C(OCH3)3 H H O OCH2CH3 NHC~3
-C(OCH3)3 H H O OCF2H CH3 CH
20 -C(OCH3)3 H H CF2H OCH3 CH
-C(OCH3)3 H H CF2H OCH3
-C(OCH3)3 H H OCH3 cyclo-
propy~
-C(OCH3)3 H H O OCF2H OCF2H CH
25 -C(OCH3)3 H H CH3 OCH3
-C(OCH3)3 H H OCH3 OCH3
-C(OCH3)3 H H 0 CH3 3
52

1259~i~ 3
53
TABL~ Ib CO~TI~UBD
Rl R12 R ~ ~ Y Z m P. C
-C(OC2H5)3 H H OCH3 OCH3 CH
-C(c2H5~3 H H CH3 OCH3 CH
C(~C2H5)3 H H CH3 CH3 CH
-C(OC2H5)3 H H O Cl OCH3 CH
-C(OC2H5)3 H H O Br OCH3 CH
~ 2 5)3 H CH3 H CH
-C(c2H5~3 H H O OCH3 H CH
2 5 3 H H OCH3 CH20C~H5 CH
2 5 3 H H O OCF2H OCH3 CH
-C(OC2H5)3 H H OCH3 CH(OCH3)2 CH
-C(OC2H5)3 H H CH3 C2H5 CH
-C(OC2H5)3 H H CH3 CH20CH3 CH
( 2 5)3 H H OCH3 CH20CH3 CH
-C(OC2H5)3 H H OCH3 C2H5 CH
-C(OC2H5)3 H H O Cl C2H5 CH
-C(OC2H5)3 H H O OCH2CH3 ~HCH3
-C(OC2H5)3 H H O OCF2H CH3 CH
-C(OC2H5)3 H H CF2H OC~3 CH
2 5 3 H H CF2H OCH3
-C(OC2H5)3 H H OC~3 cyclo-
propyl
C(C2H5)3 H H O OCF2H CF2i~ CH
25-C(~c2H5)3 H H CH3 OCH3
-C~c2H5)3 H H ~H3 OCH3
-C(OC2H5)3 H H O CH3 3
53

L3
~4
TABLE Ib CON~INUED
R R12 R W X Y Z m.P. ~C
5 ~C(OCH2CH2CH3)3 H H O OC ~ OCH3 CH
-C(OCH2C~2~H3)3 ~ H O CH3 OC~ CH
-C(OCH2CH2~H3)3 H H O CH3 CH3 CH
-~(OCH2CH2CH3)3 H H O Cl OC
-C(OC~2CH2c~3~3 H H O CH3 OC~3
-C(~CH2CH2CH3)3 H H O OCH3 O~H3 N
-C~C2H5)(0CH3)2 ~ H O OC~ ~H3 OH
-C(c2H5)(0cH3)2 H H O CH3 nCH3
-C(C2H5)(0CH3)2 H H O C ~ CH3 CH
-C(C2H5)(0CH3)2 H H O C~ OC ~ N
-C(C2H5)(CH3)2 H H O nCH3 OCH3 N
C(n C3H7)( 3)2 H O OCH3 OCH3 CH
2-ethyl-1,3- H H O OCH3 OCH3
dioxolan-2-yl .
2-ethyl-1,3- H H O C~ OCH3 CH
dioxolan-2-yl
20 2-ethyl-1,3- H H C C~ OCH3 N
dioxolsn-2-yl
2-propyl-1,3- H H O ~ OCH3 CH
dioxolan-2-yl
2-propyl-1,3- H H O ~ U H3 CH
dloxolan-2-yl
25 2-proPyl-1.3~ H H O C~ ~eH7 N
dioxolan~2-yl
S~

~2~ 3
~A~LE Ic
OE ~E~AL STRUCTUR~ Ic
Rl ~12 R ~ ~ Y Z m.p. C
1,3-dioxolan-2-yl H H O CH3 CH3 CH
5 1,3 dioxolan-2-yl H H OCH3 CH3 CH
1,3-dioxolan-2-yl H H OCH3 OCH3 CH
1,3-dioxol~n-2-yl H H O Cl OCH3 C~
1,3-dioxolan-2-yl H H O OCH3 OCH3 N
1,3-dioxolan-2-yl H H O CH3 OCH3
1,3-dioxolan-2-yl H H O OCF2H OCH3 CH
1,3-dioxolan-2-yl H H WH2CH2F ~HCH3
1,3-dioxolan-2-yl H H O OCH2CH2F OC2H5 N
1,3-dioxolan-2-yl H H O OCH2CHF2 OCH3
1,3-dioxolan-2-yl H ff O OCH2CF3 ~HCH3 N
1,3-dioxolan-2-yl H H 05~2CF3 N(C~3)2 N
1,3-dioxolan-2-yl H H O OCH2CF3 OCH3 N
1,3-dloxolan-2-yl H H O CF3 OCH3 CH
1,3-dioxolan-2-yl H H O I OCH3 CH
1,3-dioxolan 2-yl H H O Br OCH3 CH
20 1,3-dioxolan-2-yl H H O F OCH3 CH
1,3-dioxolan-2-yl H H CH3 2 5
1,3-dioxolan-2-yl H H CH3 CH20CH3 CH
1,3-dioxolan-2-yl H H O CH3 CH~SCH3 CH
1,3-dioxolan-2-yl ~ H O OCF2H OC~2H CH
1,3-dioxolan-2-yl H H O OCH3 ~HCH3 CH
1,3-dioxolan-2-yl H H O OCH3 3 3 N
1,3-dioxolan-2-yl H H O OCH3 C2H5
1,3-dioxolan-2-yl H H O CH3 OCH2CH20CH3 CH
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl
30 1~3-dioxolan-2-yl H H OCH3 SCF H CH
1,3-dioxolan-2-yl H H OCH3 ~'H(OCH3)2 CH
1,3-dioxolan-2-yl H H 0 OCH3 1,3-dioxolan-2-yl CH
1,3-~ioxolan-2-yl H H CH3 OCH C - CH
1,3-dioxolan-2 yl H H O CH3 OCH2CH=CH2 CH

59~3
56
T~BLE Ic CO~T1oU2D
Rl R12 P~ W X Y Z 1~ p. C
1,3-dio~olan-2-yl H H O OCH3 CH20C2H5
1,3-dioxolan-2-yl 4-CH3 H O OCH3 CH3 M
1,3-dioxolan-2-yl 4-C2H5 H O OCH3 CH3 CH
1,3-dioxolan-2-yl 4-C1 H OCH3 CH3 CH
1,3-dioxolan-2-yl H CH3 0 CH3 CH3 CH
1,3-dioxolan-2-yl H HS CH3 CH3 CH
1,3-d~thiolan-2-yl H HO CH3 CH3 CH
1,3-dithiolan-2-yl H HO OCH3 CH3 CH
1,3-dithiolan-2-yl H H 3 3 CH
1,3-dithiolan-2-yl H HO Cl OCH3 CH
1,3-dlthiolan-2-yl H . 3 3
1,3-dithiolan-2-yl H 3 3
CH~OCH3)2 H HO CH3 CH3 CH
CH(OCH3)2 H HQ OCH3 CH3 CH
CH(OCH3)2 H H3 3 CH
CH(OCH3)2 H HO Cl OCH3 CH
20 CH(OCH3)2 H HO OCH3 ocH3
CH~OCH3)2 H ~3 3
2 5 2 H HO CH3 CH3 CH
( 2 5 2 H HO OCH3 CH3 CH
CH(C2~5)2 H HO OCH3 OCH3 CH
CH(C2H5)2 H HO Cl OCH3 CH
( 2 5 2 H HO OCH3 OCH3
2 5 2 H H3 3
CH(SCH3)2 H HO CH3 ~H3 CH
CH(SCH3) 2 H HO OCH3 CH3 CH
30 CH(SCH3)2 H H3 3 CH
CH(SCH3)2 H HO Cl OCH3 CH
CH(SCH3)2 H HO OCH3 OCH3
CH(SCH3)2 H H3 3 M
C(CH3)(0CH3~2 H HO CH3 OCH3 CH
56

~s~
57
- ~L~
1 R12 R W ~ Y Z m p C
C(CH3)(0CH3)2 H H CH3 OCH3
5 C(cH3)(scH3)2 H H CH3 OCH3 CH
C(CH3)(SCH3)2 H H C~3 OC~3
2-methyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
2-methyl-1,3- H H O CH3 OCH3 M
~ioxolan-2-yl
4-metbyl-1,3- H H O CH3 OCH3 CH
~ioxolan-2-~1
4-methyl-1,3- ~ H O CH3 OCH3
dioxolan-2-yl
1,3-oxathiolan-2-yl H H O CH3 ~CH3 CH
15 1,3-oxathiolan-2-yl H H O CH3 OCH3
2-methyl-1,3- H H O CH3 oc~3 CH
dithiolsn-2-yl
2-methyl-1,3- H H O CH3 OCH3
dithiolan-2-yl
hexahydro-1,3-dimethyl- H ~ O CH3 OCH3 CH
pyrimid~n-2-yl
hexahydro-1,3-dimethyl- H H 0 CH3 OCH3
pyrimidin-2-yl
4,5-~imethyl-1,3~ H ~ O CH3 OCH3 CH
dioxolan-2-yl
4,5-dimethyl-1,3- H H V CH3 OCH3
dioxolan-2-yl
4-ethyl-1,3- H H O C~3 OCH3 CH
dioxolan-2-yl
4-~thyl-1,3- H H C~3 C~3
dioxolan-2-yl
1,3-dimethyl-2- H H O CH3 oc~3 CH
imidazolidinyl
1,3-dim~thyl--2- H H O CH3 OCH~
imidazolidinyl

~.2S9~3
58
~ABL~ Ic CO~TI~UED
Rl R12 R W ~ Y Z m D. ~C
-C(OCH3)3 H H 3 3 CH
5 -C(OCH3)3 H H CH3 OCH3 CH
-C~OCH3)3 H H CX3 CH3 CH
-C(OCH3)3 H H O Cl OCH3 C~l
-C(OCH3)3 H H C~3 OCH3
-C(OCH3)3 H H OCH3 QCH3
10-C(OC2H5)3 H H 3 3 CH
-C(OC2H5)3 H H 3 r 3 CH
( 2 5)3 H H CH3 ~H3 CH
2 5)3 H H O Cl OCH3 CH
( 2 5 3 H H CH3 OCH3
15 -C(OC2H5)3 H H O OCH OCN
( 2 2 3 3 H H 3 3 CH
-C(OCH2C~2CH3)3 H H CH3 OCH3 CH
( 2 2 3 3 H H CH3 CH3 CH
-C(OCH2CH2CH3)3 H H O Cl O~H3 CH
2 2 3 3 H H CH3 OCH3
2 2 3 3 H H OC~3 C~3
58

~IL2S~ L3
~9
TABL13 Id
GEUERAL STRUCTURE Id
12 Z ln P. ~C
_ _ __ _ _ --
1,3-dioxolan-2-yl H H O CH3 CH3 CH
5 1,3-dioxolan-2-yl H H O OCH3 CH3 CH
1,3-~ioxolan-2-yl H H O OCH3 OCH3 CH
1,3-dioxolan-2-yl H H O Cl OCH3 C~
1,3-dioxolan-2-yl H H O OCH3 OCH3 N
1,3-dioxolan-2-yl H H O CH3 OCH3
10 1,3-dioxolan-2-yl H H O OCF~H OCH3 CH
1,3-dioxolan-2-yl H H O CH2cH2Y ~HCH3
1,3-dioxolan-2-yl H H O OCH2CH2F OC2H5
1,3-dioxolan-2-yl H H O OCH2CHF2 OCH3
I,3-dioxolan-2-yl H H O OCH2CF3 NHCH3 N
1,3-dioxolan-2-yl H H CH2cF3 ~(CH3)2 N
1,3-dioxolan 2-yl H H O OCH2CF3 OCH3 N
1,3-dioxolan-2-yl H H O CF3 OCH3 CH
1,3-dioxolan-2-yl H H O I OCH3 CH
1,3-dioxolan-2-yl H H O Br OCH3 CH
20 1~3-~ioxolan-2-yl H H o F . OCH3 CH
1,3-dioxolan-2-yl H H O CH3 C2H5 N
1,3-dioxolan-2-yl H H O CH3 CH20CH3 C~
1,3-dioxolan-2-.yl H H O CH3 CH2SCH3 CH
1,3-dioxolan-2-yl H H O OCF2H OCF2H CH
~5 1,3-~ioxolan-2-yl H H O OCH3 3
1,3-dioxolan-2-yl H H O OCH3 ~OCH3)CH3 N
1,3-dioxolan-2-yl H H O OCH3 C2H5
1,3-dioxolan-2-yl H H O CH3 OCH2CH20CH3 CH
1,3-dioxolan-2-yl H H O OCH3 cyclopropyl
1~3-dioxolan-2-yl H H O OCH3 SCF2H CH
1,3-dioxolan-2-yl H H O OCH3 CH(OCH3~2 CH
1,3-~ioxolan-2-yl H H O OCH3 1,3-dioxolan-2-yl CH
1,3-dioxolan-2-yl H H O CH3 OCH C-CH
1,3-dioxolan-2-yl H H O CH3 OCH2CH-CH2 CH
59

1~9~
TABL~ Id CO~TI~V~D
Rl R12 R ~ ~ Y Z m e~_~
1,3-dioxolan-2-yl H H O OCH3 CH20C2H5 N
1,3-dioxolan-2-yl CH3 H OCH3 CH3 N
1,3-dioxolan-2-yl C2H5 H OCH3 CH3 CH
1,3-dioxol~n-2-yl Cl H OCH3 CH3 CH
1,3-dioxolan-2-yl H CH3 0 CH3 ~ 3 CH
1,3-dioxolan-2-yl H H S CH3 CH3 CH
lO 1,3-dithiolan-2-yl H H CH3 CH3 CH
1,3-dithiolan-2-yl H H OCH3 C~3 CH
1,3-dithiolan-2-yl H H O OCH3OCH3 CH
1,3-dithiolan-2-yl H H O Cl OCH3 CH
1,3-dithiolan-2-yl H H O OCH3 OCH3
1,3-dithiolan-2-yl H H O OCH3 CH
CH(OCH3)2 H H CH3 CH3 CH
CH(OCH3)2 H H O OCH3 3
CH(OCH3)2 H H OCH3 OCH3 CH
CH(OCH3)2 H H O Cl OCH3 CH
20 CH~OCH3)2 H H OCH3 QCH3 N
CH(OCH3)2 H H O OCH3 3
CH~OC2H5)2 H H CH3 CH3 CH
( 2 5 2 H H OCH3 CH3 CH
( 2 5 2 H H OCH3 OCH3 CH
25 CH(c2H5)2 H H O Cl OCH3 CH
2 5 2 H H OCH3 O~H3
CH(~C2H5)2 H H O OCH3 3
CH(SCH3~2 H H CH3 CH3 CH
CH(SCH3)2 H H OCH3 ~H3 Cff
30 CH(SCH3)2 H H ~CH3 OC~3 CH
CH(SCH3)2 H H O Cl OCH3 CH
CH(SCH3)2 H H OCH3 OCH3
CH(SCH3~2 H H O OCH3 3
C(CH3)(0CH3)2 . H CH3 OCH3 GH
C(CH3)(0CH3)2 H H CH3 3 1 CH

61
TABL~ I~ CONTI~U~D
~ '
R12 R W ~ Y Z m p. C
( 3)( 3 2 H H CH3 OCH3
C(CH3)(SCH3)2 H H CH3 OCH3 CH
C(CH3)(SCH3)2 H H CH3 OCH3
2-methyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
2-methyl-1,3- ~ H O CH3 OC~3
dioxolan-2-yl
4-methyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
4-methyl-1,3- H H O CH3 OCH3
dioxolan-2-yl
1,3-oxathiolan-2-yl ~ H O CH3 OCH3 CH
15 1,3-oxathiolan-2-yl H H O CH OCH3
2-methyl-1,3- H H O CH3 OCH3 CH
dithiolan-2-yl
2-methyl-1,3- H H O CH3 ~CH3
dithiolan-2-yl
hexahydro-l 3-dimethyl- H H O CH3 OCH3 CH
20 pyrlmidin-2-yl
hexahydro-1,3-dimethyl- H H O CH3 OCH3
pyrimidin-2-~1
4,5-~imethyl-1,3- H H O CH3 OCH3 CH
dioxol&n-2-yl
4,5-dimethyl-1,3- H H O CH3 ~CH3
25 dioxolan-2-yl
4-ethyl-1,3- ~ H O CH3 OCH3 CH
dioxolan-2-yl
4-ethyl-1,3- H H O CH3 OCH3
~ioxolan-2-yl
1 3-~imethyl-2- H H O CH3 OCH3 CH
30 imidazolidinyl
1,3-dimethyl-2- H ~ O CH3 OCH3
imidazoliainyl

~L~SC36~3
6~
TABLE It CO~TI~URD
Rl R12 R W X Y Z m P. C
-C(OCH3)3 H H 3 3 CH
5 -C(OCH3)3 H H CH3 OCH3 CH
~C(OCH3)3 H H O CH3 3
-C(OCH3)3 H H O Cl OCH3 CH
-C(OCH3)3 H H CH3 OCH3
-C(OCH3)3 H H OCH3 OCH3
10-C(OC2H5)3 H H 3 3 CH
-C(OC2H5)3 H H CH3 OC~3 CH
2 5 3 H H CH3 CH3 CH
2 5 3 H H O Cl OCH3 CH
-C(OC2H5)3 H H CH3 OCH3
15-C(c2H5)3 H H O OCH3OCH3
-C(OCH2CH2c~3)3 H H 3 3 CH
-C(OCH2CH2CH3)3 H H C~3 OCH3 CH
-C(OCH2CH2CH3)3 H H CH3 CH3 CH
-C(OCH2CH2CH3)3 H H O Gl OCH3 CH
2 2 3 3 H H CH3 OCH3
-C~OC~2CH2CH3)3 H H 3 3

63
TABL~ Ie
G8N~RAL ~TRUCTU~æ Ie
m.p.
Rl ~12 R W X Y C
1,3-dioxolan-2-yl H H O CH3 CH3 GH
1,3-d~oxolan-2-yl H H O OCH3 CH3 CH
1,3-dioxolan-2-yl H H O OCH3 OCH3 CH
1,3-dioxolan-2-yl H H O C1 OCH3 CH
1,3-dioxolan-2-yl H H O OCH3 OCH3 N
1,3-dioxolan-2-yl H H O CH3 OCH3 N
1,3-dioxolan-2-yl H H O OCY2H OC~3 CH
1,3-dioxolsn-2--yl H H OCH2CH2F ~HCH3
1,3-dioxolan-2-yl H H O OCH2CH2F OC2H5 N
1,3-dioxolan-2-yl H ~ O OCH2CHP2 OCH3
1,3-dioxolan-2-yl ~ H O OCH2CF3 ~HCH3
1,3-dioxol~n-2-yl H H O OCH2CF3 ~(C~332 N
1,3-diox~lan-2-yl H H O OCH2CF3 OCH3
1,3-dioxolsn-2-yl H K O CF3 OCH3 C~
1,3-dioxolan-2-yl H H O I OCH3 CH
1,3-~ioxolan-2-yl H H O Br OCH3 CH
2Q 1,3-~ioxolan-2-yl H H O F OCH3 CH
1,3-~ioxolan-2-yl H H O CH3 2 5
. 1,3-dioxolan-2-yl H H O CH3 CH20CH3 CH
1,3-dioxolan-2-yl H H O CH3 CH2SCH3 CH
1,3-dioxolan-2-yl H H O OCF2H OCF2H CH
1,3-dio~olan-2-yl H H O OCH3 ~HCH3 CH
1,3-~ioxolan-2-yl H H O OCH3 ( 3) 3
1,3-dioxolan-2-yl H ~ o OCH3 C2H5 N
1,3-dioxolan-2-yl H H O CH3 OCH2CH20CH3 CH
1,3-dioxolan-2-yl H H o OCH3 cyclopropyl
1,3-dioxolan-2-yl H H O OCH3 SC~2H CH
1,3-~ioxolan-2-yl H H O OCH3 CH(OCH3)2 CH
1,3-dioxolan-2-yl H H O OCH3 1,3-dioxolan-2-yl CH
1,3-dioxolsn-2-yl H H O CH3 OCH C-CH
1,3-dioxolan-2-yl H H O CH3 OCH2CH=CH2 CH
63

'3~i~3
6~
TABL~ I~ COUTI~U~D
Rl R12 ~ W ~ Y Z m p. C
1,3-dioxolan-2-yl H H OCH3 CH20C2~l5
1,3-dioxolan-2-yl CH3 H O OCH3 3
,3-~ioxolan-2-Yl C2H5 ~ o OCH3 CH3 CH
1,3-~iox~lan-2-yl Cl H O OCH3 CH3 CH
: 1,3-dioxolan-2-yl H CH3 CH3 CH3 CH
1,3-dioxolan-2-yl H H S CH3 CH3 CH
1~3-dithiolan-2-yl H H O CH3 CH3 CH
1,3-dithiolan-2-yl H H OCH3 CH3 CH
1,3-dithiolan-2-yl H H OCH3 OC~3 CH
1,3-dithiolan-2-yl H H O Cl OCH3 CH
l,3-dithiolan-2-yl H H O OCH3 OCH3
1 3-dlthiolan-2-yl H H OCH3 CH3 ~
CH(OCH3~2 H H CH3 CH3 CH
CHtOCH3)2 H H OCH3 CH3 CH
CH(OCH3)2 H H OCH3 OCH3 CH
CHtOCH3)2 H H O Cl OCH3 CH
CH(OCH3)2 H H OCH3 OCH3
CH(OCH3)2 H H O OCH3 3
CH(C2H5)2 H H CH3 CH3 CH
2 5 2 H H OCH3 C~3 CH
CH(C2H5)2 H H OCH3 OCH3 C~
2 5 2 H O Cl OCH3 CH
CH(e2H5)2 H H OCH3 OCH3
( 2 5)2 H O OCH3 3
CH(SCH3)2 H H CH3 CH~ CH
CH(SCH3)2 H H OCH3 CH3 CH
CH(SCH332 H H OCH3 OCH3 CH
CH~SCH3)2 H H O Cl OCH3 CH
CH(SCH3)2 H H OC~3 C~3
CH(SCH3)2 H H O OCH3 3
C(CH3)(0CH3)2 H H CH3 OCH3 CH
S4
.

~9~i~3
~BLS Ia CO~TI~V~D
R12 R W X Y Z m p. C
C(CH3)(0CH3)2 H H CH3 OCH3
C(CH3)(SCH3)2 H H CH3 O~H3 CH
C(CH3)(SCH3)2 H H CH3 OC~3
2-methyl-1,3- H H O CH3 OCH3 CH
dioxola~-2-yl
2-methyl-1,3 H H O CH3 OCH3
dioxolan-2-yl
4-methyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
4-methyl-1,3- H H O CH3 OCH3 U
dioxolan-2-yl
1,3-oxathiolan-2-yl H H CH3 OCH3 CH
1,3-oxathiolan-2-yl H H O CH3 OCH3
2-methyl-1,3- H H O CH3 OCH3 CH
dithiolan-2-yl
2-methyl-1,3- H H O CH3 OCH3
dithiolan-2-yl
hexahydro-1,3-dimetbyl- H H O CH3 OCH3 CH
20 pyrlmidln-2-yl
hexahydro-1,3-dimethyl- H H O CH3 OCH3
pyri~idin-2-yl
4,5-dimethyl-1,3- H H O CH3 OCH3
dioxolan-2-yl
4,5-dlmethyl-1,3- H H O CH3 OCH3
25 ~ioxolan-2-yl
4-ethyl-1,3- H H O CH3 OCH3 CH
dioxolan-2-yl
4-ethyl-1,3- H H O CH3 OCH3
dioxolan-2-yl
1,3-dimethyl-2- H H CH3 OCH3 CH
30 imidazolidinyl
1,3-dimethyl-2- H H O CH3 OC~3
imidazolidinyl

~259~3
T~BLE I~ COllTI~U~D
Rl R12 ~ ~ X Y Z m
--C ( OCH3 ) 3 H H OC~3 OCH3 CH
~C(OCH3)3 H H C~3 OCH3 CH
-C(OCH3)3 H H CH3 C~3 CH
-C(OCH3)3 H H O Cl OCH3 CH
-C(OCH3)3 H H CH3 OCH3
-C(OCH3)3 3 3
10 -C(OC2H5)3 H H OCH3 OC~3 CH
( 2 5 ) 3 H H CH3 ~CH3 CH
-C(OC2H5)3 H H CH3 CH3 CH
-C(OC2H5)3 H H O Cl OCH3 CH
-C(OCZH5)3 H H O CH3 OCH3
15 -C(OC2H5~3 3 3
-C~OCH2CH2CH3)3 H H OC~3 OCH3 CH
-C(OCH2CH2CH3)3 H H C~3 OCH3 CH
-C ( OCH2CH2CH3 ) 3 H H CH3 CH3 CH
-C(OCH2CH2CH3)3 H H O Cl OCH3 CH
20 -C(OCH2CH2C~3~3 H H CH3 OCH3 D
-C ( OCH2CH2GH3 ) 3 3 3
~5

6~3
67
TABLE II
Gene~al Structur~ II
Rl 11 W X Y Z m.p. C
1,3-dloxolan-2-yl CH3 H O CH3 CH3 CH
1,3-dioxolan-2-yl CH3 H O CH3 OCH3 CH
1,3-dioxolan-2-yl CH3 H O OCH3 OCH3 CH
1,3-dioxolan-2-yl CH3 H O Cl OCH3 CH
1,3-dioxolan-2-yl CH3 H O CH3 OCH3 M
1,3-dioxolan-2-yl CH3 H O OCH3 OCH3
1~3-dioxolan-2-yl C~3 H OCH~c}l2F ~HCH3
1,3-dioxolan-2-yl C~3 H O OCH2CF3 ~HCH3
1,3-dioxolan-2-yl CH3 H O OCH3 CH20CH3 CH
1,3-dioxolan-~-yl CH3 H O OCH3 cyclo- CH
propyl
1,3-dioxolan-2-yl C3H7 H O OCH3 ~ CH3 CH
1 3-diox~lan-2-yl CH3 H S CH3 CH3 CH
1,3-dioxolan-2-yl CH3 CH3 O CH3 CH3 CH
CH(OCH3)2 3 O OCH3 CH3 CH
CH(OCH3)2 3 O OCH3 CH3 N
CH(OCH3)2 3 O CH3 CH3 CH
CH(OCH3)2 3 O Cl OCH3 CH
1,3-dlthiolan-2-yl CH3 H O OCH3 CH3 CH
1,3-dithiolan-2-yl CH3 H O OCH3 3
1,3-dithiolan-2-yl CH3 H O CH3 GH3 CH
1,3-dithiolan-2-yl CH3 H O Cl OCH3 CH
67

~L~5~ iL3
68
T~BLE II CO~TI~U~D
1 Rll ~ W X Y Z m ~. C
-C(OCH3)3 CH3 H OCH3 OCH3 CH
-C(OCH3)3 3 CH3 OCH3 CH
5-C(OCH3)3 3 3 3 CH
-C(OCH3)3 3 Cl OCH3 CH
-C(OCH3)3 3 CH3 OCH3
-C(OCH3~3 3 OCH3 OCH3
-C(c2H5)3 3 OCH3 OCH3 CH
10-~(C2H5)3 3 CH3 OCH3 CH
2 5 3 3 3 3 ~H
-~(C2H5)3 3 Cl OCH3 CH
-C(c2H5)3 3 CH3 OCH3
-C(OC2H5)3 CH3 H O O~H3 OCH3
68

9~3
~9
TA~LE lI~
General Structura IIa
1 Rll R W X Y Z m p. C
1,3-dioxolan-2-yl 3 O CH3 CN3 CH
1~3-~ioxolan-2-yl 3 O CH3 OCH3 CH
1,3-dioxolan-~-yl 3 O OCN3 OCH3 CH
1,3-~ioxolan-2-yl 3 O Cl OCH3 CH
1,3-dioxolan-2-yl CH3 H O CH3 3
1,3-dioxolan-2-yl 3 O OCH3 OCH3
1~3-dioxolan-2-yl 3 O OCH2CH2F ~HC 3
1,3-dioxolan-2-yl 3 2 3 NHCH3
1,3-dioxolan-2-yl 3 O OCH3 CH20CH3 CH
1,3-~ioxolan-2-yl 3 O OCH3 cyclo- CH
1~3-~ioxolan-2-yl C3H7 H O OCN3 CH3 CH
1,3-dioxolan-2-yl 3 S CH3 CH3 CH
1,3-dioxolan-2-yl CH3 CH3 O CH3 CH3 CH
CHtOCH3)2 3 O OCH3 CH3 CH
CH(OCH3)2 3 O OCH3 CH3 M
CH~OCH3)2 3 O CH3 c~3 CH
CH(ocH3)2 3 0 Cl OCH3 CH
1,3-~ithiolsn-2-yl CH3 H O OCH3 CH3 CH
1,3-dith~olan-2-yl CH3 H O OCH3 CH3
1 3-dithiolan-2 yl CH3 H O CH3 CH3 CH
1,3-dithlolan-2-yl CH3 H O Cl OCH3 CH
69

TABLE IIa COUTINUED
Rl Rll R W X Y Z m p. C
-C~OCH3)3 3 0 OCH3 OCH3 CH
-C(OCH3)3 3 0 G~3 oc~3 CH
5-C(OCH3)3 3 0 CH3 CH3 CH
-C(OCH3)3 3 0 Cl OCH3 CH
-C(OCH3)3 3 0 CH3 OCH3
-C(OCH3)3 3 0 OCH3 OCH3
-C(c2H5)3 3 0 OCH3 OCH3 CH
10( 2 5~3 3 0 CH3 oc~3 CH
-C(c2H5)3 3 0 CH3 CH3 CH
-C(c2H5)3 3 0 Cl OCH3 CH
-C(c2H5)3 3 0 CH3 OCH3
-C(c2H5)3 3 0 OCH3 OC~3
: 25

~;~59~3
71
TABL~ IIb
General Structure IIb
Rl Rll R W X Y Z m P. C
l,3-dioxolan-2-yl 3 o CH3 3
1,3-dioxolan-2-yl 3 O CH3 OCH3 C~
l,3-dioxolan-2-yl 3 O OCH3 OCH3 CH
l,3-dioxolan-~-yl 3 O Cl OCH3 CH
; l,3-dioxolan-2-yl 3 O CH3 OCH3
1,3-dioxolan-2-yl 3 O OCH3 OCH3
1~3-dio~olan-2-yl 3 2 2 3
1,3-dioxolan-2-yl 3 2 3 ~HCH3
1,3-dioxolan-2-yl 3 O OCH3 CH20CH3 CH
1,3-dioxolan-2-yl CH H O OCH3 cyclo- CH
3 propyl
l,3-dioxolan-2-yl C3H7 H O OCH3 CH3 CH
l,3-dioxolan-2-yl 3 S CH3 CH3 CH
l,3-dioxolan-2-yl CH3 C~3 O CH3 Cl~3 CH
CH(OCH3)2 3 O OCH3 CH3 CH
CH(OCH3)2 3 O OCH3 CH3 U
CH(OCH3)2 3 O CH3 CH3 CH
CH(OCH3)2 3 O .Cl OCH3 CH
l,3-dithlolsn-2-yl CH3 H O OCH3 CH3 ~ CH
1,3-dithiolan-2-yl CH3 H O OCH3 CH3
1,3-dithlolan-2-yl CH3 H O CH3 CH3 CH
1,3-dithiolan-2-yl CH3 H O Cl ~CH3 CH

~ 2~96~L3
72
TABL~ lIb CO~TINU~D
. .
Rl Rll R W X Y ~ m,p. -C
-C(OCH3)3 3 0 OCH3 OCH3 CH
-C(OCH3)3 3 0 CH3 OCH3 CH
-C(OCH3)3 3 0 CH3 CH3 CH
. -C(OCH3)3 3 0 Cl OCH3 CH
-C(OCH3)3 3 0 CH3 OCH3
-C(OCH3)3 3 0 OCH3 OCH3 U
-C(c2H5)3 3 0 OCH3 OCH3 GH
-C(c2HS)3 3 0 CH3 OCH3 CH
-C(c2H5)3 3 0 CH3 CH3 CH
-C(c2N5)3 3 0 Cl OGH3 CH
-C(c2H5)3 3 0 CH3 OCH3
-C(c2H5)3 3 0 OCH3 OCH3 N
72

~S9~ 3
General Structure IIc
Rl Rll R W X Y Z m p. C
1,3-dioxolan-2-yl 3 O CH3 CH3 .C~
1,3-dioxolan-2-yl 3 O CH3 oc~3 CH
1,3-dioxolan-2-yl 3 O OCH3 OCH3 CH
1,3-dioxolan-2-yl 3 O Cl OCH3 CH
1,3-dioxolan-2-yl 3 O CH3 OCH3
1,3-dioxolan~2-yl 3 O OCH3 OC~3
1 3-dioxol8n-2-yl 3 2 2 3
1,3~dioxolan-2-yl 3 CH2CF3 ~HCH3
1,3-dioxolan-2-yl 3 O OCH3 CH20CH3 CH
1,3-dioxolan-2-yl CH H O OCH3 cyclo- CH
3 propyl
l~3-dioxolan-2-yl C3H7 H O OCH3 CH3 CH
1,3-dioxolan-2-yl 3 S CH3 c~3 CH
l,3-dioxolan-2-yl CH3 CH3 O ~H3 CH3 CH
CH(OCH3)2 CH3 H O OCH3 CH3 CH
CH(OCH3)2 CH3 H O OCH3 CH3 N
CH(OCH3)2 3 O CH3 CH3 CH
CH(OCH3)2 CH3 ~ O Cl OCH3 CH
1,3-dithiolsn-2-yl 3 O W ~3 CH3 CH
1,3-dithiolan-2-yl 3 o OCH3 3
1,3-~ithiolan-2-yl 3 O CH3 CH3 CH
1,3-dithiolan-2-yl 3 O Cl OCH3 CH
73

~S~ 3
74
TABI.E IIc CO~I~ D
Rl Rll R W X Y Z le p. C
-C ( OCH3 ) 3 3 0 OCH3 OC~3 CH
-C ( OCH3 ) 3 3 0 CH3 OCH3 CH
-C(OCH333 3 0 C113 CH3 CH
-C ( OC~13 ) 3 3 0 Cl OCH3 CH
-C(OCH3)3 3 0 CH3 OCH3 li
-C ( OCH3 ) 3 3 0 OCH3 QC~3
-C(C2H5)3 3 0 OCH3 OC}13 CH
10 -C(C2H5)3 3 0 CH3 OCH3 Cll
-C ( C2HS ) 3 3 0 CH3 CH3 CH
-C(c2N5)3 3 0 Cl OCH3 CH
2 5 ) 33 0 CH3 OCH3 ta
-C(OC~H5)3 3 0 OCI{3 OCH3 la

~2S9~;~3
~s
T~BL~ III
Genersl Struct~r~
Q W X Y Z m D. ~C
__ _ _ __ ._
1,3-~ioxolan-2-yl H O CH3 c~3 CH
5 1,3~dioxolan-2-yl H O CH3 OCH3 CH
1,3-~ioxolan-2-yl H O OCH3 ~CH3 CH
1,3-dioxolan-2-yl H O Cl OCH3 CH
1,3-dioxolan-2-yl H O CH3 OCH3
1,3-dioxolan-2-yl H O OCH3 OCH3
1,3-dioxolan-2-yl H OCH2CH2F NHCH3
1,3-dioxolan-2-yl H O OCH2CF3 NHCH3
1,3-dioxolan-2-yl H O OCH3 CH20CH3 CH
1,3-dioxolan-2-yl H O OCH3 cyclo- CH
propyl
1~3-dioxolan-2-yl H O OCH3 CH3 CH
1,3-dioxolan-2-yl H S CH3 CH3 CH
1,3-dioxolan-2-yl CH3 O CH3 CH3 CH
CH(OCH3)2 H O OCH3 CH3 CH
CH(OCH3)2 H O OGH3 3
20 CH(OCH3)2 H O CH3 CH3 CH
CH(OCH3)2 H O Cl OCU3 CH
1,3-dithiolan-2-yl H o OCH3 CH3 CH
1,3-dithiolan-2-yl H O OCH3 3
1,3-dithiolan-2-yl H O CH3 CH3 CH
25 1,3-dithiolan-2-yl H O Cl OCH3 CH

~5~ 3
76
TABL13 III C Ul~I21U8D
R W 3~ Y Z ~ p. ~C
-C(OCH3)3 H OCH3 OCH3 Cll
-C ( OCH3 ) 3 }I CH3 OCH3 CH
5-C ( OCH3 ~ 3 11 C~3 C113 I::H
--C ( OCH3 ) 3 H O Cl OCH3 GH
-C ( OCH3 ) 3 H C~3 OCH3 ~1
-C ( OCH3 ) 3 H OCH3 OC113 11
2 5 ) 3 H OCH3 OCH3 CHI
10-C(OC2H5)3 H CH3 OCH3 Cll
2 5 3 H C~13 CH3 CH
~C(OC2~15)3 H O Cl ~CH3 CH
-C ( C2H5 ) 3 H CH3 OC}13
-C ( C21{5 ) 3 H OCH3 OCH3 Y
76

~;~5~3
77
~BL~ IIIa
General Structur~ IIIa
Rl ~ W ~ Y Z m p. C
1,3-d~oxolan-2-yl H O CH3 CH3 CH
5 1,3-~ioxolan-2-yl H O CH3 OCH3 CH
1,3-~ioxolan-2-yl H O OCH3 OCH3 CH
1,3-dioxolan-2-yl H O C1 OCH3 CH
1,3-dioxolan-2-yl H O CH3 OCH3
1,3-dioxolan-2-yl H O OCH3 OC~3
1 3-dioxolan-2-yl H OCH2CH2F ~HCH3
1,3-dioxolan-2-yl H O OCH2CF3 ~HCH3
1,3-~ioxolan-2-yl H O OCH3 CH20CH3 CH
1,3-dioxolan-2-yl H O OCH3 cyclo- CH
propyl
1,3-dioxolan-2-yl H O OCH3 CH3 CH
1,3-dioxolan-2-yl H S CH3 CH3 CH
1 3-dioxolan-2-yl CH3 O CH3 CH3 CH
CHtOCH3)2 H O OCH3 CH3 CH
CH~OCH3)2 H O OCH3 3
20 CH~OCH3)2 H O CH3 c~3 CH
CH(OCH3)2 H O Cl OCH3 CH
1,3-dithiolan-2-yl H O OCH3 CH3 CH
1~3-dithiolan-2-yl H O OCH3 ~ CH3
1,3-dithiolan-~-yl H O CH3 CH3 CH
25 1,3-~lthiolan-2-yl H O Cl OCH3 GH

3~i~L3
78
TA~LE IIIa CO~TI~VED
Rl R W ~ Y Z ~ ~_C
-C(OCH3)3 H O OCH3 OCH3 CH
-C(OCH3)3 H O CH3 OCH3 CH
5 -C(OCH3)3 H O CH3 CH3 CH
-C(OCH3)3 H O Cl OCH3 CH
-C(OCH3)3 H O CH3 OCH3
-C(OCH3~3 H O OCH3 OCH3
-C(OC2H5)3 H O OCH3 OCH3 CH
10-C(OC2H5)3 H O CH3 oc~3 CH
-C(OC2H5)3 H O CH3 CH3 CH
-C(OC2H5)3 H O Cl OCH3 CH
2 S 3 0 CH3 OCH3
-~(OC2H5)3 H O OCH3 OC~3

36~3
79
TABLE IIIb
General Structure IIIb
Rl R W X Y Z ~ ~. C
1,3-dioxolan-2-yl H O CH3 CH3 CH
5 1,3-dioxolan-2-yl H O CH3 OCH3 CH
1,3-dioxolan-2-yl H O OCH3 OCH3 CH
1,3-dioxolan-2-yl H O Cl OCH3 CH
1,3-dioxolan-2-yl H O CH3 OCH3
1,3-dioxolan-2-yl H O OCH3 OCH3 U
1,3-dioxolan-2-yl H O OCM2CH2F oHCH3
1,3-dioxolan-2-yl H O OCH2CF3 ~HCH3
1,3-dioxolan-2-yl H O OCH3 CH20CH3 CH
1,3-dioxolan-2-yl H O OCH3 cyclo- CH
propyl
1,3-dloxolan-2-yl H O OCH3 CH3 CH
1,3-dioxolan-2-yl H S CH3 CH3 CH
1,3-dioxolan-2-yl CH3 O CH3 CH3 CH
CH(OCH3)2 H O OCH3 CH3 CH
CH(OCH3)2 H O OCH3 3
20 CH(OCH3)2 H O CH3 CH3 CH
CH(OCH3)2 H O Cl OCH3 CH
1,3-dithiolan-2-yl H O OCH3 3 CH
1,3-dithiolan-2-yl H O OCH3 CH3
1,3-dithiolan-2-yl H O CH3 CH3 CH
25 1,3-dithiolan-2-yl H O Cl OCH3 CH
79

~i25~3
~o
TABLE lIIb C013TINU13D
R W 2~ Y Z
-C ( OCH3 ) 3 H O OCH3 OCh3 C11
-C ( OCH3 ) 3 H O CN3 ' OCH3 CH
-C ( OC}13 ) 3 H O CH3 CH3 CH
-C(OCH3)3 H O Cl OC}~3 Cli
-C(OCH3)3 H O CH3 OCH3 Id
-C ( OCH3 ~ 3 H O OCH3 OCH3 U
-C ( C2H5 ) 3 H O OCH3 OCH3 CH
10 -C(OC2H5)3 H O CH3 OCH3 CH
2 5 ~ 3 H O CH3 c~3 CH
2 5 3 H O Cl OCH3 CH
2 5 3 H O C113 OCH3
2 5 3 H O OCH3 OCH3

~59~i~3
81
TABL~ IV
General 5tructure IV
Rl R2 R W Wl A ~ Yl Yz m ~. C
1,3-dioxolan-2-yl H H O S A 2 5H3 0
5 1,3-dioxolan-2-yl H H O S A-2 OCH3 0
1,3-dioxolan-2-yl H H O S A-2 OCF2H o
1,3-dioxolan-.-yl H H O S A-2 CH3 CH~ -
1,3-dioxolan-2-yl H H O S A-2 OCH3 CH~ -
1,3-dioxolan-2-yl H H O S A-2 OC2H5 CH2
1,3-dioxolan-~-yl H H O O ~-2 CH3 0
1,3-dioxolan-2-yl H H O O A-2 OCH3 0
1,3-dioxolan-2-yl H H O O A-2 OCH3 2
1,3-dith~olan-2-yl H H O S ~-2 CH3 0
1,3-dithiolan-2-yl H H O S A-2 OCH3 CH2
1,3-dith~olan-2-yl H H O O A-2 C~3 0
1,3-dithiolan 2-yl H H O O ~-2 OCH3 CH2
CH(OCH3)2 H H O S A-2 CH3 0
CH(OCH3)2 H H O O A-2 CH3 0
1,3-dioxolan-2-yl H H O S A-3 CH3
1,3-dioxolan-2-yl H H o S A-3 OCH3
1,3-dioxolan-2-yl H H O O A-3 OCF2H
1,3-dioxolan-2-yl H H O S A-4 OCH3 - . CH3
1,3-dioxolan-2-yl H H o S A-4 CH3 - 3
1,3-dioxolan-2 yl H H O S A-4 OC2H5
1,3-dioxolan-2-yl H H O o ~-4 CH3 ~C~3
1,3-~ioxolan-2-yl H H O O A-4 OCF2H ~ CH3
1,3-dithiolan-2-~1 H H O S A-3 CH3
1 3-dithiolan-2-yl H H O S A-4 C~3 ~c~3
CH(OCH3)2 H H O S A-3 OCH3
CH(OCH3)2 H H O S ~-4 OCH3 ~CH3
81

9~3
82
TABLE IY COUTI~U~
Rl R2 R W 1 A Xl Yl Y2 m.p. C
C(OCH3)3 H H O S A-2 CH3 O
C(OCH3)3 ~ H O S A-2 OCH3 O
C~OCH3)3 H H o S A-2 OCF2H O
C(OCH3)3 H H O S A-2 CH3 CH2
C(OCH3)3 H H o S A-2 OCH3 2
C(OCH3)3 H H O S A-~ OC2H5 CH2
C(OCH3)3 H H O O A-3 CH3
10 C(OCH3)3 H H O O A-3 OCH3
C(OCH3)3 H H O o A-3 OCF2H
C(OCH3)3 H H o o ~-4 OCH3 ~ CH3
C(OCH3)3 H H O O A-4 C~13 ~ c~3
C(OCH3)3 H H O O A-4 OC2H5 - H
15 C(OCH3)3 H H . O o A-4 OCF~H ~ CH3
C~OCH3)3 H H O o A-2 CH3 O
2 5 3 H H O O A-2 CH O
( 2 5 3 H H O S A-2 CH3 O
ZO
~2 Y3
C(OCH3)3 H H O S ~-5 CH3 OCH3
C(OCH3)3 H H O S A-5 CH3 C2H5
C(OCH3)3 H H O S A-5 CH3 SCH3
25C(OCH3)3 H H O S A-5 CH3 SC~5
C(OCH3)3 H H O S A-5 CH3 CH3
C(OCH3)3 H H O S ~-5 CH3 C2H5
C(OCH3)3 H H O S ~-5 CH3 OCF~H
C(OCH3)3 H H O S A-5 CH3 SCF2H
30C(OCH3)3 H W O S A-5 C~H5 OCH3
C(OCH3)3 H H O S A-5 CH2CF3 ~3
C~OCH3)3 H H O O A-5 CH3 OCW3
82

~l~S9~3
~3
TABLE IV COUTINUED
Rl R2 R W Wl A ~1 Yl Y2 ~-
1,3-dioxolan- H H o S A-5 CH3 OC~3
2-yl
1,3-~ioxolan- H H o s A-5 CH3 OC2H5
2-yl
1,3-~ioxolan- H H O S A-5 CH3 SCH3
2-yl
1,3-dioxolan- H H O S A-5 CH3 SC2~5
2-yl
1,3-dioxolan- H H o S A-5 CH3 2
2-yl
1,3-~ioxolan- H H O S A-5 CH3 SCF2~ -
2-yl
CH(OCH3)2 H H O S A-5 CH3 OC~3
CH(OCH3)2 H H o S A-5 CH3 C2H5
CH(OCH3)2 H H O S A-5 CH3 SCH3
CH(OCH3)2 H H O S A-5 CH3 SC2X5
CH(OCH3)2 H H O s A-5 CH3 OCF2H
CH(OCH3)2 H H O S ~-5 CH3 SCF2H
CH(OCH3)2 H H o o A-5 CH3 OCH3
X3
C(OCH3)3 H H O S A-6 CH3
C(OCH3)3 H H o S A-6 OCH3
25 1,3-dioxolan- N H o S ~-6 CH3
1,3-dioxolan- H H O S A-6 OCH3
2-yl
CH ( OCH3)2 H H O S A-6 CH3
CH(OCH3)2 H H O S A-6 OCH3
30 CH(OCH3)2 ~ H O O A-6 CH3
4 Y4 Z
CH(OCH3)2 H H O S A-7 CH3 CH3 CH
CH(OCH3)2 H H O S A-7 OCH3 OCH3 C~
1,3-dio~olan- H ~ O S A-7 CH3 CH3 CH
35 2-yl
1,3-dioxolan- H H o S A-7 OCH3 OCH3 CH
2_yl 83

3L~5~1L3
84
TABL~ Iy CO~TI~U~D .
_ R2 R W Wl A 1 1 Y2 m p. ~C
C(OCH3)3 H H O S A-7 CH3 CH3 CH
CtOCH3)3 H H O S ~-7 CH3 3
5 C(OCH3)3 H H O S A-7 OCH3 CH3 CH
C(OCH3)3 H H O S A-7 OCH3 3
C(OCH3)3 H H O S A-7 OCH3OCH3
C(OCH3)3 H H O æ A-7 Cl CH3 CH
C(OCH3)3 H H O S A-7 OCH3 Cl CH
C(OCH3)3 H H O S A-7 OC2H5 CH3 CH
C(OCH3)3 H H O S A-7 CH2CH3 CH3
C(OCH3)3 H H 2 3 3 CH
C~OCH3)3 H H O S A-7 OC2H5 2 5
C(OCH3)3 H H O O A-7 CH3 CH3 CH
84

~2S~3
TA8L~ IVa
Genaral Structur~ IYa
Rl Rl~ R W Wl A ~l Yl Y2 m p. C
l,3-dioxolan-2-yl H H O S A-2 CH3 0
1,3-dioxolan-2-yl H H O S A-2 OCH3 0
1,3-dioxolan-2-yl H H O S A-2 OCF2H O
1,3-dioxol~n-2-yl H H O S A-2 CH3 C~2
1,3-~ioxolan-2-yl H H O S A-2 OCH3 CH2
1,3-dioxolan-2-yl H H O S A 2 2 5 2
1,3-dioxola~-2-yl H H O O A-2 CH3 0
1,3-dioxolan-2-yl H H O O A-2 OCN3 0
1,3-dioxolan-2-yl H H O O A-2 OCH3 CH2
1,3-dithiolan-2-yl H H O S A-2 CH3 0
1,3-dithiolan-2-yl H H O S A-2 OCH3 CH
1,3-dithiolan-2-yl H H O O A-2 CH3 0
1,3-dithiolan-2-yl H H O O A-2 OCH3 CH
CH(OCH3)2 H H 0 S ~-2 CH3 0
CH(OCH3)2 ~ H O O A-2 CH3 0
1,3-dioxolan-2-yl H H O S A-3 CH3
1,3-dioxolan-2-yl H H O S A-3 OCH3
1,3-dioxolan-2-yl H H O O A-3 OCF2H -
1,3-dioxolan-2-yl H H O S A-4 OCH3 ~ CH3
- 1,3-~ioxolan-2-yl H H O S A-4 ~H3 - 3
1,3-dioxolan-2-yl H H O S A-4 OC2H5 - H
l 3-~ioxolan-2-yl H H o O ~-4 C~3 ~ CH3
1,3-dioxolan-2-yl H H O O A-4 OCF2H ~ C~3
l,3-dithiolan-2-yl H H O S A-3 CH3
1,3-~ithiolan-2-yl H H O S A-4 CH3 ~ C~3
CH(OCH3)2 ~ H O S A-3 OCH3
CH(OCH3)2 H H O S A-4 OCH3 ~ CH3

~L~5~ 3
~6
TABLE IVa CO~TlNUED
Rl R12 ~ W Wl A _1 Yl Y2 m P. C
C(OCH3)3 H H O S A-2 CH3 0
C(OCH3)3 H H O S A-2 OCH3 0
5 C(OCH3)3 H H O S A-2 OCF2H 0
C(OCH3)3 H H O S A-2 CH3 CH2
C(OCH )3 H H O S A-2 OCH3 CH2
C(OCH3)3 H H O S A-2 OC2H5 CH2
C(OCH3)3 H H O O A-3 CH3
} C(OCH3)3 H H O O A-3 OCH3
C(OCH3)3 H H O O A-3 OCF2H
C(OCH3)3 H H O O A-4 OCH3 ~ CH3
C(OCH3)3 H H O O A-4 CH3 ~ CH3
C(OCH3) H H O O ~-4 OC2H5 - H
15 C(OCH~)3 H H O O A-4 OCF2H ~ CH3
C(OCH3) H H O O A-2 CH3 0
C(C2H5)3 H H O O ~-2 CH3 0
2 5 3 H W O S A-2 CH3 0
X2 3
C(OCH ) H H O S A-5 CH3 OCH3
3 3 H H O S A-5 CH3 C2H5
C(OCH3) H H O S A-5 CH3 SCH3
C(OCH3)3 H H O S ~-5 CH3 5C2H5
C(OCH3) H H O S A-5 CH3 CH3
C(OCH3)3 H H O S A-5 CH3 C2~5
C(OCH3)3 H H S A-5 CH3 OCF2H
C(OCH3)3 H H O S A-5 CH3 SCF2H
30 C~OCH3)3 H H O S A-5 C H OCH3
C~OCH3) H H O S A-5 CH2CF3 OCH~
C(OCH3)3 H H O O A-5 CH3 OC~3
86

~5~3~3
87
TABL~ IVa CO~TINU~D
Rl R12 P~ W Wl ~ Xl Yl Y2 m p. C
1,3-~ioxolan- H H O S A-5 CH3 OC~3
2-yl
1,3-dio~olan- H H O S A-5 CH3 OC2H5
2-yl
1,3-~ioxolan- H H O S ~-5 CH3 SCH3
2-yl
1,3-dioxolan- H H O S A-~ CH3 2 5
2-yl
1~3-dioxolan- H H O S A-5 C~3 OCF2H
2-yl
1,3-~ioxolan- H H O S A-5 CH3 2
2-yl
CH(OCH3)2 H H O S A-5 CH3 OCM3
CH(OCH3)2 H H O S A-5 CH3 C2H5
CH(OCH3)2 H H O S A-5 CH3 SCH3
CH(OCH3)2 H H O S A-5 CH3 SC2H5
CH(OCH3)2 H H O S A-5 CH3 OCF2H
CH(OCH3)2 H H O S A-5 CH3 SCF2H
CH(OCH3)2 H H O O A-5 CH3 OCH3
~3
- C(OCH3)3 H H O S ~-6 CH3
C(OCH3)3 H H O S A-6 OCH3
5 1,3-dioxolan- H ~ O S A-6 C~3
2 2-yl
1,3-dioxolan- H H O S ~-6 OCH3
2-yl
CH~OCH3)2 H H O S A-6 CH3
CH(OCH3)2 H H O S ~-6 OCH3
30 CH(OCH3)2 H H O O A-6 CH
4 Y4
CH(OCH3)2 H H O S A-7 CH3 CH3 CH
CH(OCH3)2 H H O S A-7 OCH3 OCH3 CH
1,3-dioxolan- H H O S A-7 CH3 CH3 CH
2-yl
1,3-dioxolan- H H O S h-7 OCH3 05H3 OH
2-Yl a7

~;~5~3
88
TABL~ IVa CO~TI~UBD
1 R2 R Wl A Xl Yl Y2 m D. C
C(OCH3)3 H H O S A-7 CH3 3
C(OCH3)3 H H O S A-7 CH3 3
5 C(OCH3)3 H H O S A-7 OCH3 3
C(OCH3)3 H H O S A-7 OCH3 3
C(OCH3)3 H H O S A-7 OCH3 OCH
C(OCH3)3 H H O S A-7 Cl 3
C(OCH3)3 H H O S ~-7 OCH3 Cl CH
C(OCH3)3 H H O S A-7 OC2H5 CH3 CH
C(OCH3)3 H H O S A-7 CH~OCH3 CH3
C(OCH3)3 H 2 3 3
C(OCH3)3 H W O S A-7 OC2H5 C2~5u
C(OCH3)3 H H O O A-7 CH3 3

~sg~3
~9
T~BL~ IVb
G~neral Structure IVb
Rl R12 R W Wl A Xl Yl Y2 m p. C
1,3-dioxolan-2-yl H H O S A-2 C~3 0
1,3-dioxolan-2-yl H H O S A-2 OCH3 0
1,3-dioxolan-2-yl H H O S A-2 OCF2H O
1,3-dioxolan-2-yl H H O S A-2 CH3 CH2
1,3-dioxolan-2-yl H H O S A-2 OCH3 CH2
1,3-dioxolan-2-yl H H O S A-2 OC2HS C~2
1,3-dioxolan-2-yl H ~ o O A-2 CH3 0
1,3-dioxolan-2-yl H H O O A-2 OCH3 0
1,3-dioxolan-2-yl H H O O A-2 OCH3 CH~ -
1,3-dithiolan-2-yl H H O S ~-2 CH3 0
1,3-dithiolan-2-yl H H O S A-2 OCH3 CH
1,3-dithiolan-2-yl H H O O A-2 CH3 0
1,3-dithlolan-2-yl H H O O A-2 OCH3 C~ -
CH(OCH3)2 H H O S A 2 CH3 0
CH(OCH3~2 H H o o A-2 CH3 0
1,3-dioxolan-2-yl H H O S A-3 CH3
1,3-dioxolan-2-yl H H O S A-3 OCH3
1,3-~ioxolan-2-yl H H O O A-3 OCF2H -
1,3-dioxolan-2-yl H H O S A-4 O~H3 ~ c~3
1 3-~ioxolan-2-yl H H O S A-4 CH3 ~ CH3
1,3-dioxolan-2-yl H H O S A-4 OC2H5 - H
1 3-dioxolan-2-yl H U O O A-4 CH3 ~ CH3
1,3-~ioxolan-Z-yl H H O O A-4 OCF2H ~ CH3
1,3-dithlolan-2-yl H H O S A-3 CH3
1 3-~ithiolan-2-yl H H O S A-4 CH3 ~ CH3
CH(OCH3~2 H U O S A-3 OCH3
CH(OCH3)2 H H O S A-4 OCH3 ~ CH3
89

~2~96~3
TABL8 IVb COMTINVED
1 12 ~ 1 1 2
C~OCH3)3 H H O S A-2 CH3 0
C(OCH3)3 H H O S ~-2 OCH3 0
5 C(OCH3)3 H H O S A-2 OCP2H O
C(OCH3~3 H H O S A-2 CH3 CH2
C~OCH3)3 H H O S A-2 OCH3 CH2
C(OCH3)3 H H O S A-2 OC2H5 CH2
C(OCH3)3 H H O O A-3 CH3 - -
10 C(OCH3)3 H H O O A-3 OCH3
C(OCH3)3 H H O O A-3 OCF2H - -
C(OCH3)3 H H O O A-4 OCH3 - 3
C(OCH3)3 H H O O A-4 CH3 - CH3
C(OCH3)3 H H O O A-4 OC2H5 - H
C(OCH3)3 H H O O A-4 OCF2H - CH3
C(OCH3)3 H H O O A-2 CH3 0
( 2 5 3 H H O O A-2 CH3 0
( 2 5 3 H H O S A-2 CH3 0
X2 Y3
C(OCH3)3 H H O S A-5 CH3 OCH3
: C(OCH3)3 H H O S A-5 CH3 C2H5
C(OCH3~3 H H O S A-5 CH3 SCH3
C~OCH3)3 H H O S R-5 CH3 S~2H5
C(OCH3)3 H H O S A-5 CH3 C~3
C(OCH3)3 H H O S A-5 CH3 C2H5
C(OCH3)3 H H O S A-5 CH3 OCF~H
C(OCH3)3 H H O S A-5 CH3 SCF2H
C(OCH3)3 H H O S A-5 .C~H5 OCH3
C~OCH3)3 H H O S A-5 CH2CF3 OCH3
C(OCH3)3 H H O O A-5 CH3 OCH3

~1
~ABL~ IVb COUTI~UeD
Rl R12 R W Wl A Xl l Y2 ~ P- C
2 - 3
1,3-dioxolan- H H 4 S A-5 CH3 OC~3
2-yl
1,3-diox~lan- H H o S A-5 CH3 OC2H5
2-yl
1,3-dioxolan- H H O S A-5 CH3 SCH3
2-yl
1,3-dioxolan- H H O S A-5 CH3 SC2H5
2-yl
1,3-dioxolan- H H O S A-5 CH3 OCF2H
2-yl
1,3-dioxolan- H H O S A-5 CH3 2
2-yl
CH~OCH3)2 H H O S A-5 CH3 OCH3
CH(OCH3)2 . H H O S A-5 CH3 C2H5
CH(OCH3)2 H H O S A-5 CH3 SCH3
CH~OCH3)2 H H O S A-5 CH3 SC2H5
CH(OCH3)2 H H O S A-5 CH3 CF2H
CH(OCH3)2 H H O S A-5 CH3 SCF2H
zo CH(OCH3)2 H H O O A-5 CH3 OCH3
C(OCH3)3 H H O S A-6 CH3
C(OCH3)3 H H O S A-6 OCH3
25 1,3-~ioxolan- ~ H O S A-~ CH3
2-yl
1,3-dioxolan- H H O S A-6 OCH3
2-yl
CH(OCH3)2 H H O S A-6 Cff3
CH(OCH3)~ ~ H O S ~-6 OCH3
30 CH(OCH3)2 H H O O A-6 CH
4 Y4 Z
CH(OCH3)2 H H O S A-7 CH3 CH3 CH
CH~OCH3)2 H H O S A-7 OCH3 OCH3 CH
1,3-dioxolan- H H O S A-7 CH3 CH3 CH
35 2-yl
1,3-dioxolan- H H O S A-7 OCH3 OCH3 CH
91

~;~5~
TABL~ IVb COUTIUU~D
Rl R2 ~ W Wl A XlYl Y2 m P. ~C
C(OCH3)3 H H O S A- 7 CH3 3
C~OCH3~3 ~ H O S A-7 CH3 3
5 C(OCH3~3 H H O S A-7 OCH3 3
C(OCH3)3 H H O S ~-7 OCH3 3
C~OCH3)3 ~ H O S A-7 OCH3 OCH
C(OCH3)3 H H O S A-7 Cl 3
C(OCH3)3 H H O S A-7 OCH3 Cl CH
C(OCH3)3 H H O S A-7 OC2H5CH3 CH
C(OCH3)3 H H o S A-7 CH20CH3 C~3
C(OCH3)3 H H O S ~-7 CH20CH3 OCH3 CH
C(OCH3~3 H H 0 2 5 2 5
C(OCH3)3 H H O O A-7 CH3 3

~:5~ L3
~3
TABLe V
~eneral Structur~ V
Rl 11 A Xl 1 ~2 m P. C
1,3-dioxolan-2-yl CH3 H o A-2 3
1,3-dioxolan-2-yl CH3 H O A-2 OCF2H O
1,3-dioxolan-Z-yl CH3 H O A-2 OCH3 0
1,3-dioxolan-2-yl CH3 H O A-2 CH3 CH2
1,3-dioxolan-2-yl CH3 H O A-2 OCH3 CH2
1,3-dioxolan-2-yl CH3 H O A-2 0C2~5 CH2
1~3-dithiolan-2-yl CH3 H ~-2 C~3 0
1,3-dithiolan-2-yl CH3 H O A-2 OCH3 CH2
1,3-~ioxolan-2-yl CH3 H O A-3 3
1,3-dioxolsn-2-yl CH3 H O A-3 OCH3
1,3-dioxolan-2-yl CH3 H O A-4 CH3 ~ CH3
1,3-dioxolan-2-yl CH3 H A-4 OCH3
1,3 dioxolan-2-yl CH3 H O A-4 OCF2H ~ C~13
93

~5~3~:3
94
TABL~ V CO~ UED
Rl R~ 2 R W 1~l Xl Y2 Y m P. C
C(OCH3)3 3 H O A-2 CH3 0
C(OCH3)3CH3 H H O A-3 CH3 - -
C ( OCH3 ~ 3 3 H O A-4 CH3 ~ CH3
g2 Y2
C ( OCH3 ) 3 3 H O A-5 CH3 ~ OCH3
1, 3-dioxolan- 3 H O A-5 CH3 SCH3
10 2-yl
C(CH3) (CH3)2 3 H O A-6 CH3
C ~ OCH3 ) 3 3 H O Pa-6 OC113
~4 Y4. Z
1, 3-dioxolan- 3 H O A-.7 CH 3
2-yl
C(OCH3)3 3 H O A-7 OCH3 OCH3 CH
ZS
94

~25~ L3
TABL~ V~
General StruCtUrQ Ya
Rl Rll R W A Xl Yl Y2 m.p. C
1,3-dioxolan-2-yl CH3 H O A-2 3
1,3-d~oxolan-2-yl CH3 H O A-2 OCF~ O
1,3-dioxolan-2-yl CH3 H O A-2 OCH3 0
1,3-dioxolan-2-yl CH3 H O A-2 CH3 CH2
1,3-dioxolan-2-yl CH3 H O A-2 OCH3 CH2
l,3-dioxolan-2-yl CH3 H O A-2 2 5 2
1~3-dithiolan-2-yl CH3 H O A-2 CH3 0
1,3-dithiolan-2-yl CH3 H O A-2 OCH3 CH2
1,3-dioxolan-2-yl CH3 H O A-3 3
1,3-dioxolan-2-yl CH3 H O A-3 OCH3
1,3-dioxolan-2-yl CH3 H O A-4 C~3 ~ c~l3
1,3-Aioxolan-2-yl CH3 H O A-4 OCH3 - H
1,3-dioxolan-2-yl CH3 H O A-4 OCF2H ~ CH3

~5~ 3
96
TA~LE Va CO~TI~UeD
Rl 11 W A 1 1 Y2 m P. ~C
C(OCH3)3 3 A-2 CH3 0
C(OCH3)3 3 A-3 CH3 - -
5 C(OCH3)3 3 A-4 CH3 ~ CH3
~2 Y2
C(OCH3)3 3 A-5 CN3 OCH3
1, 3-dioxolan- 3 A-5 CH3 SC~3
2-yl
~3
C(CN3) (0CH3)2 3 ~-6 CH3
C ( OCH3 ) 3 3 A-6 OCH3
:~4 Y4 .
1, 3-dioxolan- 3 A-7 ~H3 3
2-yl
C(C~3)3 3 3 3

96~3
97
TABL~ Vb
Gensral Structure Vb
Rl Rll R W A Xl Yl Y2 m ~. C
1,3-~ioxolan-2-yl CH3 H o ~-2 3
1,3-dioxolan-2-yl CH3 H O A-2 2
1,3-dioxolan-2-y} CH3 H O A-2 OCH3 O
1,3-dioxolan-2-yl CH3 H O A-2 CH3 CH2
1,3-~ioxolan-2-yl CH3 H O A-2 OCH3 CH2
1,3-dioxolan-2-yl CH3 H O A-2 C2H5 CH2
1,3-dithlolan-2-yl CH~ H O A-2 CH3 O
1,3-dithiolan-2-yl CH3 H O A-2 OCH3 CH2
1,3-dioxolan-2-yl CH3 H O A-3 CH3 - -
1,3-dioxola~-2-yl CH3 H O A-3 OCH3
1,3-dioxolan-2-yl CH3 H O A-4 CH3 ~ CH3
1,3-dioxolan-2-yl CH3 H O A-4 OCH3 - H
1,3-dioxolan-2-yl CH3 H O A-4 2 C~3
C(OCH3)3 3 A-2 CH3 O
C(OCH3)3 CH3 H O A-3 3
c~OCH3)3 3 A-4 CH3 ~ CH3
X2 Y3
C(CH3~3 3 . A-5 CH3 OG~3
1,3-dioxolan- 3 A-5 CH3 SCH3
2-y~
~3
C(CH~)(OcH3)23 A-6 CH3
C(OCH3)3 CH3 H O A-6 OCH3
~4 Y4
1,3-dioxolan- 3 A-7 CH3 3
2-yl
C(OCH3)3 3 3 3
~5
97

~5''3~3
9~
TABLE Vc
General Structur~ Vc
Rl Rll R W A Xl Yl Y2 m p. C
1, 3-dioxolan-2-yl C113 H O A-2 3
1,3-dioxolan-2-yl CH3 H O A-2 2
1, 3-dioxolan-2-yl CH3 H O A-2 OCH3 0
1, 3-dioxolan-2-yl CH3 H O A-2 CH3 CH2
1 ,3-dioxolan-2-yl CH3 H O A-2 OCH3 CH2
1, 3-dioxolan-2-yl CH3 H O A-2 2 5 2
1, 3-dithiolan-2-yl CH3 H O A-2 3
1,3-dithiolan-2-yl CH3 H O A-2 OCH3 CX2
1, 3-dioxolan-2-yl CH3 H O A-3 3
1, 3-dioxolan-2-yl CH3 H O A-3 OCH3
1, 3-dioxolan-2-yl CH3 H O A-4 CH3 ~ CH3
1,3-dioxolan-2-yl Cl{3 H O A-4 3
1, 3-dioxolan-2-yl CH3 H O A-4 2 3
C t OCH3 ) 3 3 A-2 CH3 0
C ( OCH3 ) 3 3 A-3 CH3
C ( OCH3 ) 3 3 A-4 CH3 ~CH3
X~ Y3
C ( OCH3 ) 3 3 A-5 CH3 OCH3
1, 3-dioxolan-CH3 H O A-5 CH3 SCH3
~-yl
X3
c(CH3) (CH3)23 A-6 CH3
C(OCH3)3 CH3 H O A-6 OCH3
3 0 g4 Y4 Z
1, 3-dioxolan- 3 A-7 CH3 3
2-yl
C ( OCH3 ) 3 3 A 7 3 3
~8

3l~5~3~j~L3
99
~ABLE YI
rzne-~l 5t~u~t~ n Vl
Rl R W A Xl Yl Y2 m.p. ~C
5 1,3-dioxolan~2-yl H O A-2 CH3 O
1,3-d~oxolan 2~yl H O A-2 DCF2H 0
1,3-d~oxolan-2 yl H O A-2 OCH3 O
1,3-dioxolan-2-yl H O A-2 CH CH2
1,3-dioxolan-2-yl H O A-2 OCH3 CH2
lo 1,3-dioxolQn-2-yl ~ A 2 OC2~5 CH2
1,3-d~thiolan-2-yl H O A-2 CH3 0
1,3-d~thiolan-2-yl H O A-2 OCH3 G~2
1,3-dioxolan-2-yl H D A-3 CH3 - -
1,3-dioxolan-2-yl H O A-3 OCH3 -7
1,3-dioxolan-2^yl H O A-4 CH3 - 3
1,3-dioxolan~2-yl H O A-4 OC~ - H
1,3-dioxolan-2-yl H O A-4 OCF2H ~ CH3
C(OCH3)3 CH3 O A-2 CH ~ 3
G(OCH3)3 C~3 O ~-3 CH3
C(OCH3)3 CH3 O A-4 ~H3 - CH~
C(QCH3)3 ~H~ O ~-S CH3 OC~
1,3-d~oxolan- CH3 O A-5 ~ ~ SCH3
2-yl
C(CH3)(0CH3)2 CH3 O A-6 ~
C(OCH3~ 3 O A 6 D~H _ 3
~ Y4 Z
1,3~dloxolan- CH3 O A-7 ~H ~3 CH~
2-yl
~ 3)3 CH3 O A-7 OCH OCH3 CH 3

~;~5~ L3
10~
~ABLE VIa
Genersl Struoture VIa
1 R W A Xl Yl Y2 m.p. C
1,3-dioxolan-2-yl H O R-2 CH3 0
1,3-dioxolan-2-yl H O A-2 OCF2H O -
1,3-d~oxolan-2-yl H O A-2 OCH3 0
1,3-dioxolan 2-yl H O A-2 CH3 CH2
1,3-d-oxolan-2-yl K O A-2 OCH~ CH2
1,3-dioxolan-2-yl H n A-2 OC2H5 CH2
1,3-dithlolan-2-yl H O A-2 CH3 0
1,3-d~th1olan-2-yl H O A-2 OCH3 CH2
1,3-dioxolan-2-yl H O ~-3 CH3 - -
1,3-dioxolan-2-yl H O A-3 OCH3
1,3-dloxolan-2-yl H O A-4 CH3 ~ ~H3
1 ,3-dioxolan-2-yl H O A-4 OCH S - H
1,3-dioxolan-2-yl H O A^4 OCF2H ~ CH3
C(OCH~)3 CH O A-2 C ~ O
C(OCH3)3 CH O Q-3 CH3
~(OCH3)3 CH O A-4 CH3 ~ CH3
~ Y3
C(CCH3)3 CH3 0 A-5 CH3 OCH3
1,3~dioxolan- CH~ O A-5 OH3 SCH3
Z5 2-yl
-
C(~H3)(0CH3)2 CH O A-6 C ~ - -
C(OCH3)3 CH~ O A-6 OCH3
X4 Y4
1,3 dioxolan- CH3 D A-7 ~H3 CH~ OH
2-yl
~(OCH3)3 ~H3 0 A-7 OCH3 O~H3 GH
1~0

~L~5~3
lnl
General Structure VIb
Rl R W A Xl Yl Y2 m.~. ~C
5 1,3-dioxolan-2-yl H O ~-2 CH3 D - :
1,3-diqxolan-2-yl H O ~-2 OCF2H O
1~3-dioxolan-2-yl H O A-2 QCH3 0
1,3-dioxolan-2-yl H O ~2 CH3 ~H2
1,3-dioxolan-2-yl H O A-2 OCH3 CH2
1,3-dioxolan-2-yl H O A-2 OC2H5 GH2
1,3 dithiolan-2-yl H O A-2 CH~ O
1,3-dith~olan-2-yl H O A-2 CCH~ CH2
1,3-dioxol~n-2-yl H O A-3 CH3 - -
1,3-dloxolan-2-yl H C A-3 OCH3
a 5 1,3-dioxolan-2-yl H O A-4 CH3 ~ ~H3
1,3-dioxolan-2-yl H O A~4 OCH3
1,3-dioxolan-2-yl H O A-~ OCF2H ~ CH3
C(OCH3)3 CH~ O A-2 CH3 0
C(OCH3)3 CH3 0 A-3 CH3 ~ -
C(OCH3)3 CH3 o ~-4 ~H3 CH3
X2 y
= 3
~(OCH3)3 CH3 0 A-~ ~H3 UCH3
1,3-dioxolan-CH3 0 A-~ CH3 SCH3
25 2-yl
C~CH3)(0CH332CH3 0 A-~ ~H3 - -
C(OCH3)3 CH3 0 A-6 OC ~ - -
~4 Y4 Z
1,3-d~oxolan-CH3 ~ ~-7 CH3 ~H3 CH
2-yl
~(CCH3~3 CH3 0 A-7 OCH3 OCH3 CH
101

~2S96~3
102
TAaL~ VII
General Structure VII
1 R Rl~ E W X Y Z m ~. C
C(OCH3)3 H H ~ CH3 CH3 CH
5 C(OCH3)3 H H ~ CH3 OCH3 CH
C(OCH3)3 H H ~ OCH3 OCH3 CH
C(OCH3)3 H H - O Cl OCH3 CH
C(OCH3)3 H H - O Br oc~3 CH
C(OCH3)3 H H _ O CH3 ~ CH
lO C(OCH3)3 H H ~ OCH3 H CH
C(OCH3)3 H H ~ OCH3 CH20C2M5 C~
C(OCH3)3 H H - O OCF2H OCH3 CH
C(OCH3)3 H H ~ OC~3 CH(OCH3)2 CH
C(OCH3)3 H H ~ CH3 C2H5 C~
C(OCH3)3 H H ~ CH3 CH20CH3 CH
C(OCH3)3 H H ~ OCH3 CH20CH3 CH
C(OCH3)3 H H ~ OCH3 C2H5 CH
C(OCH3)3 H H - O C2H5 OCH3 CH
C(OCH3)3 H H - O OCF2H OCF2H CH
20 C(OCH3)3 H H ~ CH2F ~CH3 CH
C(OCH3)3 H H - O CH2Cl OCH3 CH
C(OCH3)3 H H - O CF OCH3 CH
C(OCH3)3 H H - O Cl C2H5 CH
C(OCH3)3 H H - O OCH2CH2F OC~3 CH
: 25 C(OCH3)3 H H - O CH2cF3 OCH3 CH
C(OCH3)3 H H ~ CH3 OCH3
C(CH3)3 ~ ~ ~ OCH3 OCH3
C(OCH3)3 H H - O CH3 3
C(OCH3)3 H H - O OCH3 cyclo-
C(OCH3)3 H H - O C2H5 ~HCH3
C(OCH3)3 H H - O CH2cF3 OCH3
C(OCH3)3 H H - O OCH2CH2F CH3
C(OCH3)3 H H - O CH2cH2~ OCH3
102

103
TABLE VII COUTI~UED
Rl R R14 E W X Y 2 m P. C
CSOCH3)3 H H - S OCH3 OCH3 CH
C(OCH3)3 H 3-F - o OCH3 OCH3 CH
5 C(OCH3)3 H 5-Cl - O OCH3 OCH3 CH
C(OCH3)3 H 5-CH3 - o OCH3 oc~3 CH
C(OCH3~3 2 5 O OCH3 OCH3 CH
CtOCH3)3 H 6-OCH3 - O OCH3 OCH3 CH
C(OCH3)3 H 6-OC2H5 - O OCH3 OCH3 CH
10C(OCH3)3 H 6-SCH3 - O OCH3 OCH3 CH
C(OCH3)3 H 6-SC2X5 - O OCH3 OCH3 CH
C(OCH3)3 H 5-Br - O OCH3 QCH3 CH
C(OCH3)3 H H CH2 O OCH3 OCH3 CH
( 2 5 3 H H CH2 O CH3 CH3 CH
lSC(0C2H5)3 H H CH2 O CH3 OCH3 CH
( 2 5 3 H H CH2 O OCH3 OCH3 CH
( 2 5 3 H H CH2 0 Cl QCH3 CH
( 2 5 3 H H CH2 0 CH3 OCH3 N
2 S 3 H H CH2 O OCH3 OCH3
ZC(OCH2CH2¢H3)3 H H CH2 O OCH3 OCH3 CH
C(OCH2CH2CH3)3 H H CH2 CH3 OCH3 CH
C(OCH2C~2cH3)3 .~ H CH2 O CH3 CH3 CH
C(OCH2CH~CH3)3 H CN2 O Cl OCH3 CH
C( 2 2 3 3 CH2 O CH3 OC~3
25C(OCH2CH2CH3~3 H H CH2 0 0CH3 OCH3
C(OCH3)3 CH3 H CH2 0 OCH3 OCH3 CH
C(OCH3)3 H H CH2 O C~2cHF2 CH3
C(OCH3~3 H H CH2 O CH3 3 7
103

~L~59~
1~4
TABL~ VII C0UTINU~D
14 Z ~ P. C
~ _ _ _ _ _ _
C(OCH3)3 H H - O OCH3 ~(OCH3~CH3
C(OCH3)3 H H ~ CH3 ~(CH~)3
5 C(OCH3)3 H H _ O OC~3 CF3 CH
C~OCH3)3 H H ~ CH3 ~CH3
C(OCH3)3 H H ~ CH3 OCH2CH-CH2
C(OCH3~3 H H ~ CH3 OcH2cH~cH
C(OCH3)3 H H ~ CH3 CH2SCH3
lO C(OCH3)3 H H - O OCH3 SCF2H CH
C(OCH3)3 H H - O OCH3 1,3-dioxolan-2-yl CH
C(OCH3) H H - O OCH3 4-methyl-1,3-
3 dioxolan~2-yl
C(OCN ) H H - O OCH3 4-ethyl-1,3- CH
3 3 dioxolan-2-yl
C(OCH3)3 H H - O OCH3 1,3-~ithiolan-2-yl C~
C(OCH3)3 H H - O OCH3 1~3-oxathlolan-2-yl ~
C(OCH3)(OC2H5)2 H H _ 0 OC~3 OCH3 CH
C(OC2H5)(OCH3)2 H H _ O OCH3 OCH3 CH
2-~ethoxy-1,3- H H - 3 3 CH
~ dioxolan-2-Yl
2-ethoxy-1,3- H H 3 3 CH
dioxolan-2-yl
,
104

105
T~BL~ VIla
General Structure VIIa
al 14 E W A 1 1 Y2 ~ P- C
C(OCH3)3H H - O A-2 3
C(OCH3)3 H H - O A-2 OCH3 0
C(OCH3)3 H H - O ~-2 OCH3 CH2
C(OCH3)3 H H - O A-2 ~CF2H
( 2 5 3 A-2 C~3 0
C(C2H5)3 H H - O A-2 OCH3 0
C( 2 2 3)3 3
( 2 2 3)3 3
C(OCH3)3 H H - O ~-3 3
C(OCH3~3 H H - O A-3 OC~13
C(OCH3)3 H H - O A-4 CH3 - CH3
C(OCH3)3 H H - O ~-4 OCH3 - CH3
C(OCH3)3 H H - O ~-4 OCH3 - H
2 3
20C(OCH3~3 H H - O A-5 CH3 OCH3
C(OCH3)3 H H - O A-5 CH SCH3
C(OCH3)3 H H - ~-5 CH3 .CH3
. ~3
25 C(OCH3)3 H H - O ~-6 C~3
C(OCH3)3 H H - O ~-6 OCH
4 Y4 Z
C(OCH3)3 ~ ~ - ~-7 CH3 CH3 CH
30C(OCH3)3 H H - O A-7 OC~3 OCH3 CH
C(OCH3)3 ~ ~ - ~-7 ~C~3 OCH3 U
105

~5~ 3
106
Formulations
Useful formulation6 of the compound6 of
Formula I can be prepared in conventional ways. They
include du~ts, granules, pellet6, solutions.
su6pensions, emulsion~, wet~able powder6, emulsifiable
concentrate6 and the like. Many of the~e may be
applied directly. Speayable formulations can be
extended in suitable media and u~ed a~ ~pray volumes
of from a ~ew liter6 to 6everal hundred lite~s per
hectare. High strength compo6itions are primarily
u~ed as intermediates for further ~ormulation. The
formulations, broadly, contain about 1~ to 99% by
weight of active ingredient(s) and at lea~t one of ~a)
about 0.1~ to 20% ~urfactant(s) and (b) about 5% to
99~ ~olid or liquid diluent(6~. More ~pecifically,
t~ey will contain the~e ingredients in the following
approximate proportions:
Weight Percent*
Active
Inqredient Diluent(6) Surfactant(s)
Wettable Powder~20-90 0-74 1-10
Oil Suspen~ion6,5-50 40-95 0-15
Emulsion6, Solutions.
(including Emulsifiable
Concentrates)
Aqueous Suspension 10-50 40-84 1-20
Dust~ 1-25 70-99 0-5
Granules and Pellets 1-95 5-99 0-15
High Strength 90-99 0-10 0-2
30 Composition~
* Active ;ngredient plu~ at leas~ one of a Surfactant
or a Diluen~ equals 100 weight percent.
106

~S~
107
Lower or higher lev~l8 0~ aceiY~ in9r~die~t can,
of course. be prasene depanai~g o~ th~ inte~d~d u~
and ~e p~y6~al propertle~ o~ t~e compou~d. High2r
ratios of 6ur ac~ant ~o ac~ve ~ngred~Qnt are ~ome-
5 times desirable, and ar~-achieved by incorporation
into the for~ulation or by t~nk mixi~g.
Typical solid diluent6 are de~cribed ~n ~atkins,
et al., ~Handbook of In6ec~i~ide DUfit ~iluent~ and
Carrier6~, 2nd ~d., Dorland BooksO Caldwell, New
lo Jer6ey. ~he more absorptive diluent~ are pr~ferred
for wettable powders and t~e denser ones for du6ts.
Typical liquid diluents and ~olve~t~ are desceibed i~
Marsden, "Solvents~Guide," 2nd Ed.. I~ter6cience, New
Yor~, 1950. Solubility under O.lt i~ prefer-red ~or
suspension concentrates: solueion concentrates ar~
~reerably 6table agai~st pha~e separa~io~ at 0C-.
- ll~cCutcheQn ' 6 Deter.gent~ and Emul~ifiers Annual"~, ~C
Publi~hin~ Corp., Ridgewood, New Jer~ey, a6 well a~
Sisely and ~ood, ~Encyclopedia of Sur~ace Active --
Agents", Che~ical Publi~hing Co., Inc., New York,
- 1964, li~t surfactants and recommended use~0 All
formulation6 can con~ain minor amount6 of addieives to
r~duce foami~g, caking, corrosio~, ~icrobiological
growth, etc. Pre~era~ly, i~gredient~ ~hould b~
25 approved by the appropriate governmental body for the
use intended.
Ths ~ethods of ~aking ~uc~ co~positions are well
knswn. Solutaon6 are prepared by simply mi~ing the
in~redient~. Fine ~olid compo~ition6 are made by
blending and, usually, ~indin~ a~ in a ham~er or
fluid energy mill. Suspension~ are prepared by wet
milling (~ee, for example, Littler. U.S~ Pa~ent
3,060,084). Granule6 and pellet6 may be made by
~praying the active material upo~ preor~ed granular
carriers oc by agglomeration ~echniques.
107

12~36~3
10~
In the following example~, all par~s are by
weight unless otherwise i~dicated~
Example 5
Wettable Powder
3-(1,3-dioxolan-2-yl)-N-t(4-methoxy-6-methyl-
1,3,5 triazin-2-yl)aminocarbo~yl]-2-thiophene-
sulfonamide 80%
60dium alkylnaphthalene ulfona~e 2%
sodium lignin~ulfonate 2%
synthetic amorphou6 silica 3%
kaolînite 13%
The ingredient6 are blended, ha~mer-milled until
all the 601id6 are essentially under 50 microns, re-
blended, and packaged.
Example 6
~ettable Powder
N-~(4,6-dimethoxypyeimidin-2-yl)aminocarbonyl]-3-
(1,3-dioxolan-~-yl)-2-thiophene6ulfonamide 50%
sodium alkylnaphthalene6ulfonate 2%
low vi6c06ity methyl cellulo6e2%
diatomaceous earth 36%
The ingredients are blended, coar6ely hammer-
milled and th~n air-milled to produce particles es6en-
tially all below 10 micron in diameter. The product
is reblended before packaging.
- ~xample 7
High Strength Concentrate
3-(1,3-dioxolan-2-yl)-N-t(4-methoxy-6-methyl-
1,3,5-triazin-2-yl)aminocarbo~yl]-2-thiophene-
~ulfonamide 99%
~ilica aerogel 0.5%
synthetic amor~hou6 6ilica 0.5%
The ingredient6 are blended and ground in a hammer-
mill to produce a material es6entially all pa6sing a
U.S.S. No. 50 ~creen (0.3 mm opening). The concentra~e
may be foemulated further if nece~ary.
1~

36~L~
10~
Exam~le 8
Wet~able Powder
3-(1,3-dioxolan-2-yl)-N-~4-methoxy-6-methyl-
1,3,5-~riazi~-2-yl~aminocarbonyl~-2-thiophene-
sulfonamide 20%
60di.um alkylnaphthalenesulfona~e ~%
~odium ligninaulfonate 4%
low vi~coaity methyl celluloae 3%
at~apulgite ~9%
The ingredient6 aee thoroughly blended. After
grinding in a hammer-mill to produce particles esse~-
tially all below 100 micron6, the material i6 ee-
blended and ~ifted through a U.S.S. No. 50 6ieve (0.3
mm opening) and packaged.
15 . '
Oil Sua~en~ion
N-[(4,6-dimetho~ypyrimidin-2-yl)aminocarbonyl]-3-
(1,3-dioxolan-2-yl)-2-thiophenesulfonamide 25%
polyoxyethylene sorbitol hexaoleate 5%
zo highly aliphatic hydrocarbon oil 70%
The ingredientR are ground together in a sand
mill until the ~olid particle~ have been reduced to
under about 5 microns. The re6ulting thic~ ~u~pen~ion
may be applie.d directly, bu~ preferably after being
extended with oil~ or emul~ified in water.
~xa~Ple 10
Oil Suspension
3-(1,3-dioxolan-2-yl)-N- r ( 4-methoxy-6-methyl-
1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-
8ulf onamida 35%
blend o~ polyalcohol carboxylic 6S
ester~ and oil aoluble petrolaum
6ulfonate6
xylene 59S
The ingredien~ are combined and ground together
in a sand mill to produce particles e~aentially all
109

~25t~
110
below 5 micron~. The product can be u6ed directly,
extended with oil6, or emul~ified in water.
Example 11
Aqueou~ su~Pension
5 3~ 3-dioxolan-2-yl)-N-[(4-methoxy-6-meehyl-
1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-
~ulfonamide 40%
polyacLylic acid thickener 0.3%
dodecylphenol polyethylene
glycol ether 0,5%
di60dium ~ho6phate 1%
mono60dium pho6phate o.~%
polyvinyl alcohol 1.0%
water 56.7%
The ingredients are blended and ground together
in a sand mill to ~roduce particle~ e~entially all
under 5 microns in ~ize.
Example 12
Solution
3-(1,3-dioxolan-2-yl)-N-t(4-methoxy-6-methyl-
1,3,5-triazin-2-yl)aminocarbonyl~-2-~hiophene-
6ulfonamide 30%
dimethylformamide 70~
The ingredient6 are combined and ~tirred t-o produce
a solution, w~ich can be u~ed for low volume application~.
ExaM~l e 13
Du~3t
wettable powder of Example 6 10~
Pyrophyllite tpowder) 90%
The wettable powder and the pyrophyllite diluen~
are thoroughly blended and then packaged. The product
i8 ~uitable for u6e a a du~t.
3 !~i
110

1~ rj9~3
111
examPle 14
Low Strenath Granul~
3-(1,3-dioxolan-2-yl~-N-~(4-methoxy-6-methyl-
1,3,~-triazin-2-yl)aminocarbonyl]-2-thiophene-
sulfonamide 0.1
attapulgite granuleR 99.
(U.5.S. 20-40 me~h)
The active ingredient is di~601ved in the 601-
vene and the ~olution i~ sprayed u~on dedusted gran-
ule~ in a double cone blender. After spraying of thesolution ha~ been completed, the material is warr~ed to
evaporate the solven~. The material i~ allowed to
cool and then pa~kaged.
ExamPle 15
15 Granule
Wettable Powd~r of Example 6 5%
attapulgite granules 95
(U.S.S. 20-40 mesh: 0.84-0.42 mm)
A 61urry of wettable powder containing 25%
~olid~ i sprayed on the ~urface of attapulgi~e
granules in a double-cone ble~der. The qEanules are
dried and packaged.
~ xample_16
Granule
N-t(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-
(1,3-dioxolan-2-yl)-2-thiophene~ulfona~ide ~o%
wetting agent 1%
crude lignin~ul~onate ~alt (con~aining 10%
5-20% of the natural sugae6~
attapulgite clay 9%
The ingredient~ are blended and milled to pas~
through a 100 mesh ~creen. This material i8 ~hen
added to a fluid bed g~a~ulator, the air ~low i~
~dju~ted to gently 1uidi2e the material, and a
fine spray of water i~ sprayed onto the fluidized
111

5~ 3
112
material. The fluidization and spraying are continued
until granule6 of the desi~ed size range ar~ ma~s.
The 6praying ;~ stopped, bu~ ~luidizatio~ ~5
continued, optionally with heat, until the water
content i8 reduced to the desired level, generally
les~ than 1~. The material i6 then di6charged,
screened to the desired 6ize range, generally 14-lOo
me6h (1410-149 micron~)~ and packaged for use.
ExamPle 17
Extruded Pellet
3-(1,3-dioxolan-2-yl)-N-[(~-methoxy-6-methyl-
1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-
sulfonamide 2S%
anhydrou6 60dium sulfate 10%
crude calcium ligninsulfonat~ 5
60dium alkylnaphthalene~ulPonate 1
calcium/magnesiu~ bentonite 59~
The ingredientfi are blended, hammer-~illed and
then moistened with about 12% water. The mixture is
extruded as cylinder6 about 3 mm diameter which are
cut to produce pellet6 about 3 mm long. These may be
used directly after drying, or ths dried pellet~ may
be c~u6hed to pa~ a U.S.S. No. 20 ~ieve (0.84 mm
opening~). The qranules held on a U.S.S. No. 40 sieve
(0.42 mm opening6) may be packaged for u~e and the
fine~ recycled.
11

~25~
113
Utility
Test reRult~ indicate that the compound of the
pre6ent invention are active herbicidas. They have
utility for broad-~pec~rum prs- and/or po~t-emergence
5 weed control in area where co~plete control of all
vegetation i~ de~ired, such a~ around fuel 6torage
tank~, ammunition depot~, industrial ~orage areas,
parking lot~, drive-in theaters, around billboards,
highway and railroad structure~. Alterna~i~ely, ~he
6ubject compound~ are ufieful to modify plant growth.
The rate6 sf application for the compound6 of
the invention are determined by a number of factors,
including their u~e a~ plane g~owth modifier6 or a~
herbicides, the crop specieg involved, the type6 of
weeds to be controlled, weather and climate,
formulations 6elected, mode of application, amount of
foliage present, etc. In general term6, the 6ubject
compound6 ~hould be applied at level of around 0.01
to 5.0 kg/ha, the lower rate~ being ~ugge6ted for use
on lighter 60ils and/~r those having a low organic
matter content, for plant growth modification or for
6ituation~ where only 6hort-term per6i6tence is
required.
The compounds of the invention may be u6ed i~
combination with any other commercial herbicide:
example6 of which are those of th~ triazine, triazole,
uracil, urea, amide, diphenylether, carbamate and
bipyridylium type~.
The herbicidal propertie6 of the subject co~-
pound~ were discovered i~ a number of greenhousete~t~. The test procedure~ and re~ults follow.
113

6~;3
114
CO~Pt)UNDS
~O ~NHCoNH4(~
CH3
Coml2ound 1
/~0~ OCH
~S02NHCONH~
N
OCEI3
Compound 2
CH3
20C (OCH3 ) 2 OCH
~S02NHCONH~
OCH3
25ComPound 3
CE~3
~¢, C t OCH3 ) 2 OCH
3O~S~ So2NHCoNH4(~
CH3
Compound
llg

6~
115
COMPOUNDS CO~T I NUED
CH3
C ( OCH3 ) 2 OCH3
NHcoNH~
CH3
ComE~ound 5
CH ( OCH3 ) 2 ,OCH3
NHcoNH~)
N~
~CH3
ComPound 6
-
CH ( OCH3 ) 2 O~H3
20~so2NHcoNH~
OCH3
Compound 7
25~5H(CH3 ) 2 OCH3
~ so2~Hc:~NE~ N
c~3
Com~Qund 8
115

116
COMPOUND5 CONTINUED
CEI ( OCH3 ) 2 QCH3
5~so2NHcoNE~
Cl
Compol~nd 9
lS
116

117
Test A
Seeds of cr2bgrass (Diqitaria Bp. ~, barn-
yardgras~ (Echinochloa cruR~alli), wild oat~ (AYena
~atua), si~klepod (Cassia ob~usifolia), morningglory
(Ipomoea ~pp.), cocklebur ( anthium pensylvan~cum),
sorghum, co~n. soybean, 6ugar beet. cotton, rice,
wheat and eurple nut~edge (CYperus rotundus) ~uber6
were planted and treated pre-emergence with the test
chemicals dis~olved in a non-phytotoxic ~olvent. At
the same time, these crop and weed 6pecies were
treated with a 60il/foliage application. At the time
of treatment, the plant~ ranged in height from 2 to
18 cm. Treated plant6 and control~ were ~aintained in
a greenhouse for six~een days, after which all 6pecie~
were compared to control~ and ~isually rated for
re6pon~e to treatment. The rating6, ~ummarized in
Table A, are based on a numerical scale ~xtending from
O - no injury, to 10 = co~plete kill. The accompany-
ing de~criptive symbols have the ~ollowing meaning~:
C , chloro~i6 or necrosis;
B = burn
D = defoliation
E = emer.gence inhibition;
G = growth retardation; and
H = formative effects.
U = unusual pigmentation
= axillary stimulation
S = albini6m
6Y = ab~ci6ed buds or flowers.
117

118
Tabl~ A
ComPound 1 ComE~ound 2
Rate kg/ha O . 05 o . 05
POST -~MERGENCE
C o c k 1 e bur 9C 1 OC
Sicklepod 2C, 5G 7G
Nut edge 3C, 8G 5CC, 9G
Sa r nya 1~ d g r a 8 s SC, 9 H 5C, 9G
S o r qhum 9G 5C, 9G
Co t t on lOC 9C
PRE-EMERGENOE
Morningglory 9G 4C, 9
Cocklebur 8H 9H
2 0 Sa ~ ny a ~ d gr a s s 2 C, 5G 17 H~ G
Whld Oats 6C5G9G 4C 9G
2 5 R 1 c e SC, 9R 6C, 9H
Cotton 2CC 9~ 9G
118

~Z5~3~3
119
Table A Continued
Compound 3 Compound 4
5 Rate kgfha 0.05 0.05
POST-EMERGENCE
Morningglory lOC lOC
Cocklebur 4C,9H 9C
Velvetleaf 9C 9C
Nutsedge 9C 8C
10 Crabgrass 7H 7G
Barnyardgrass 9C 9C
Cheatgra66 lOC 6C,9G
Wild Oat6 2C,SG 2G
Wheat 2~ 2G
Corn 7U,9C lOC
Soybean 9C 9C
15 Rice 9C gC
Sorghum 5C.9H 2U,8~ -
Sugar beet 9C 9C
Cotton 9C 9C
PRE-EMæRCENCE
Morningglory 9C 9G
Cocklebur 7H 8H
20 Velvetleaf lOC 9C
Nutsedge lOE lOE
Crabgras6 2C,7G 4C,9G
Barnyardgra6~ 9H 9~
Chea~gras~ . 4C.9H 3G,9H
Wild Oats 8G 8G
~heat 2C,8H 8G
Corn 9~ 4C,9
Soybean 8H 9H
Rice 10~ lOE
Sorghum 9H 3C,9H
Sugar bee~ 5C.9G 5C,9G
Cotton 9G 9G
119

~ ~ 5
120
Table A Continued
ComPound 5 ComPound 6
5 Rate kg/ha 0.05 0.05
POST-EMERGENCE
Morningglory lOC lOC
Cocklebur 9H 9C
Velvetleaf 2C~7G 9C
Nut6edge 4G 9C
10 Crabgras6 2G 2C,6G
Barnyardgra~s 9C 3C,9H
Cheatgra~s 0 3C,8G
~ild Oat~ o O
~heat O O
Corn 7U,9C 2C,~
Soybean 5C,9G 5C,9G
15 Rice 4C,8G 4C,9G
Sorghum 3C,9~ 4C,9
Sugar beet 9C 9C
Cot~on 5C.9G 9C
PRE-EMERGENCE
Morningglory 9G 9H
Cocklebur 3H 3H
20 Velvetleaf 5G 9G
Nut6edge 3G 2C,9
Crabgra~6 2G O
Barnyardgrass 3C,7G 4C,9H
Cheatgras~ 6G 3C,8G
~ild Oat6 3G 5G
Wheat 2G 4G
25 Corn 2C,9G 8G
Soybean 2C,5G 9H
Rice 3C,8H 4C,9H
Sorghum ~C,9H 4C,8H
Sugar beet 5C,9G 9C
Cotton 2C.8G sa
120

:~59~3
121
Table A Continued
ComPound 7 ComEound 8 ComPound g
5 Rate kg/ha 0.05 0~05 0.05
POST-EME~GENCE
Morningglory 6C,9G 9C lOC
Cocklebur 9G lOC 9C
Velvetleaf 6C,9G lOC 9C
Nutsedge 6G 3G 4C,8G
10 Crabgra~s 5G 4G O
Barnyardgras6 4C,9H 4C,9~ 8H
Cheatgrass 0 2C,3H O
Wild Oat~ O O O
Wheat O o o
C~rn 2C,9G 5C,9G 1
Soybean 5C,9G 5C,9G 3H,9G.7
15 Rice 7G 5G 6G
Sorghum 3C.9H 5C,9H 9H
Sugar beet 3C.9G 9C 9C
Cotton 9C 9C sC
PRE-EM~RGENCE
Morningglory8H 8G 3G
20 Cocklebur 9H 5G 7G
Velvetleaf 4C,8G 3C,8G 4G
Nutsedge 9 3G 3G
Crabgrass 0 0 0
Barnyardgra~s 0 3C,7ff 4G
Cheatgra~s 3G 0 0
Wild oats O O O
25 ~he~t g O O
Corn 2C,8H 3C,9H 4G
~oybean 3C~8H 3C,8H 5
Rice 3C,5H 3C,7G o
Sorghum 3C,9H 5C,9H 2Cp7G
Sugar bee~ 5C,9G 5C,9G 7G
Cotton 3G,8G BG 8G
121